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NOBUYOSHI KANENIWA, NOBUTOSHI WATARI, HISAKO IIJIMA
1978 Volume 26 Issue 9 Pages
2603-2614
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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Experiments were made on the effect of particle size on gastrointestinal drug absorption in the rabbit and its relation to solubility using powder drugs, in a series of solubility ranging from 1 to 25 mg/ml at 37°in suspension, and a consideration was made on the relationship between solubility and bioavailability on the basis of particle size, with following results. 1) The blood concentration-time curves at the particle size up to some sizes showed a similar time course curve obtained with an aqueous solution of each drug. Provided that the maximum particle size limit which described a time course curve similar to that of solution was the critical particle size (CPS), effect of particle size on the blood level appeared above the CPS of a drug. The CPS depended mainly on the solubility with slight relation of individual absorption rate of each drug solution and increased linearly with an increase in solubility. The extent of availability for different particle size grades was almost constant in each powder drug. 2) General consideration was made on the relationship between solubility and bioavailability on the basis of a particle size. This relation may vary with other factors, especially, dosage forms such as tablet, capsule, etc., physiological factors, and individual properties of the drugs. However, this relation would be useful as a temporary standard as for considering the relationship between solubility and bioavailability on the basis of particle size.
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TSUTOMU KAMEYAMA, TOSHITAKA NABESHIMA, MAKOTO UKAI, KAZUMASA YAMAGUCHI
1978 Volume 26 Issue 9 Pages
2615-2618
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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The effects of morphine on the 3-methoxytyramine (3-MT) and normetanephrine (NM) level of various brain sites and two parts of spinal cord were investigated in mice with reference to our prior data on the effects of catecholaminergic agents on the morphineinduced Straub tail reaction (STR). Morphine (10 mg/kg) increased the 3-MT and NM content in the thoracic and lumbar regions of the spinal cord significantly, without affecting the 3-MT or NM content of the various brain sites. Naloxone (1 mg/kg) antagonized the morphine-induced increase in the 3-MT and NM in the thoracic and lumbar cord. These results suggest that morphine accelerates the release of spinal dopamine and norepinephrine. The morphine-induced STR might be due to the acceleration of catecholaminergic neuronal activities in the spinal cord in mice.
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ISAO IKEUCHI, TAMEYUKI AMANO
1978 Volume 26 Issue 9 Pages
2619-2623
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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To measure sodium mercaptoundecahydrododecaborate (I), Na
2B
12H
11SH, used for boron neutron-capture therapy, a colorimetric method with curcumine for determining boron in biological materials was developed. First, biological samples such as the tumor, surrounding tissues, and blood plasma were ashed gently using the radiofrequency combustion system with excited oxygen plasma. Urine samples were not ashed but usually required dilution with water. After oxidative degradation with potassium permanganate, boron in the degradation products was extracted with chloroform containing 2-ethyl-1, 3-hexanediol. Boron in the chloroform extract was converted into the boron-curcumine complex by adding an acetic acid solution of curcumine, followed by concentrated sulfuric acid. After dilution with 95% (v / v) ethanol, the absorbancy of the solution at 554 nm based on the complex was measured by spectrophotometry. The linear dynamic range for the assay was from 0.5 to 20 μg of boron per sample solution. Compared with the 1, 1'-dianthrimide method the present method is simple and safe, and is sensitive enough to be useful for the determination of boron in biological materials.
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MAMORU NOGUCHI
1978 Volume 26 Issue 9 Pages
2624-2629
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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Precipitation reaction was found to occur when each 5×10
-4 M aqueous solution of berberine (I) and glycyrrhizin (II) were blended. The molar ratio of I and II in the precipitate (III) was revealed to be 2 : 1 by observation of UV absorption at 251 and 350 nm. By comparison of the IR absorption near at 1715 and 1620 cm
-1 of II, III, soyasaponin III and glycyrrhetinic acid after treated at various pH, it was revealed that the quartery base moiety of I bound on the glucouronic acid moieties of II ionically in compound III. The solubility of III in aqueous solution was 0.09% at pH 3.5, while it increased up to 1.9% at pH 6.8. The solubility of III was slightly decreased by addition of II in aqueous solution.
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AKIRA MIZUTANI, MOTOHIRO TANAKA
1978 Volume 26 Issue 9 Pages
2630-2634
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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End group amino acid sequence was determined on a hypocalcemic protein TP
1 purified from bovine thymus gland. Amino-terminal amino acid sequence was deduced to be His-Asx-Ala-Glx- by the dansyl-Edman degradation method. Carboxyl-terminal amino acid sequence was analyzed by digestion with carboxypeptidase A and Y, and it was deduced to be-Thr-Ala-Lys. Furthermore, the carboxyl-terminal amino acid was confirmed to be lysine alone by the hydrazinolysis method. According to these results and from previous data, it became apparent that TP
1 did not bear the subunit structure, and it was clearly different from other hypocalcemic proteins obtained from bovine thymus and parotid gland.
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MAKOTO MIYAHARA, MASAHIRO NAKADATE, MICHIKO MIYAHARA, IKUO SUZUKI
1978 Volume 26 Issue 9 Pages
2635-2641
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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Nitrosation of bisureido compounds with sodium nitrite in the presence of acid was examined. The treatment of 1, 2-bisureidoethane with sodium nitrite in 6% sulfuric acid, afforded 1-carbamoyl-3-nitroso-2-imidazolidinone in 86% yield. Similarly, the same nitrosation of 1, 2-bisureidopropane gave an isomeric mixture of cyclized N-nitroso compounds in 87% yield. On the other hand, nitrosation of o-phenylenebisurea with sodium nitrite and 25% sulfuric acid, gave only cyclized 1-carbamoyl-2-benzimidazolidinone in 58% yield, and nitroso compound was not obtained. This nitrosative cyclization occurs only in 1, 2-bisureido compounds which have no substituent in the ureido nitrogens. The mechanism of this cyclization was also discussed.
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YOSHIHARU KARUBE, YUKIO ONO, YOSHIKAZU MATSUSHIMA, YO UEDA
1978 Volume 26 Issue 9 Pages
2642-2648
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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The theoretical energies and oscillator strengths of the π-π
* transitions were calculated by the Pariser-Parr-Pople type ASMO-SCF-LCAO-CI-MO method for the spectroscopic models for the active site of pyridoxal enzymes. The calculated structures are eight molecular species distinguished by the state of the protonation at the phenolate and the pyridine and azomethine nitrogens in the aldimine of 3-hydroxy-4-formylpyridine (1) with methylamine, species of the quinoid intermediate in which the α-carbon is deprotonated in the aldimine of 1 or 1-methyl-3-hydroxy-4-formylpyridinium (6) with alanine methyl ester, species of the aldimine of 6 and α-aminoacrylate anion, and species of the quinoid intermediate derived from 6 and 2-amino-3-butenoate anion. The calculated transition energies agreed satisfactorily with the observed ones and gave support for the band assignments made previously.
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YOSHIHISA MATSUDA, MARI MIHARA
1978 Volume 26 Issue 9 Pages
2649-2656
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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Five sulfonamide tablets, those of sulfaphenazole, sulfadimethoxine, sulfisomidine, sulfisoxazole, and sulfamethizole, were exposed to exaggerated and ordinary ultraviolet (UV) rays for stability studies in the solid state, and the relationship between coloration stability and chemical degradation was investigated. The color change of tablet surface was measured by colorimetric method. Sulfisoxazole and sulfamethizole were photostable in coloration, and sulfadimethoxine was eventually not colored contrary to what was stated in the Pharmacopeia of Japan. Photosensitive similarity between exaggerated and ordinary exposure was not established in coloration. Photolytic degradation was examined spectrophotometrically and crystallographically. Interesting absorption changes were observed in UV spectra, whereas no apparent changes in either infrared spectra or X-ray diffraction patterns. These evidences were discussed in relation to the results obtained by the complementary tristimulus colorimetry using the UV absorption data. For all the sulfonamides, evident correlation did not exist between coloration and photolytic degradation.
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HIDEO INOUE, TOHRU UEDA
1978 Volume 26 Issue 9 Pages
2657-2663
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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5'-O-Acetyl-2', 3'-O-isopropylidene-5-bromouridine (1) gave the 6-cyanouridine (2) by treatment with sodium cyanide at room temperature. Heating of 2 with sodium cyanide afforded the 5-cyanouridine derivative (3) by the addition-elimination mechanism. This method provides a convenient route of the preparation of 5-cyanouridine and 5-cyano-2'-deoxyuridine. The cyano function of 2 was converted to the amide, thioamide, carboxyl, hydroxymethyl, chloromethyl, methyl, cyanomethyl, and carboxymethyl group, respectively. The circular dichroism (CD) spectra of 6-substituted uridines prepared in this work showed all positive CD bands, though existed mainly as the syn-form as determined by the nuclear magnetic resonance measurements.
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HIDEO INOUE, TOHRU UEDA
1978 Volume 26 Issue 9 Pages
2664-2667
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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Treatment of 5'-acetylthio-5'-deoxy-2', 3'-O-isopropylidene-5-bromouridine, prepared from 2', 3'-O-isopropylidene-5-bromouridine, with sodium methoxide in methanol afforded 5'-deoxy-5'-thio-2', 3'-O-isopropylidene-S
6, 5'-cyclouridine. Deacetonation of the product gave 5'-deoxy-5'-thio-S
6, 5'-cyclouridine, a sulfur-bridged cyclouridine fixed in the"anti"conformation. Starting from the 5'-amino derivative a N
6, 5'-cyclouridine was similarly prepared. The nuclear magnetic resonance and mass spectra of a series of O-, N- and S-cyclouridines were compared and the characteristic features were discussed.
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ITSURO YOKOTA, SHOJI SHIBATA
1978 Volume 26 Issue 9 Pages
2668-2670
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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The polysaccharides of Stereocaulon japonicum Th. Fr. were studied to find that a cold water-soluble fraction, SJ-2-I, is an α (1→3) (1→4) glucan (2.7 : 1) (DP : 64) partially branched at 3, 4- or 2, 3-positions.
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MASAYUKI SHIBUYA, KENICHI ABE, YOSHITAKA NAKAHASHI, SEIJU KUBOTA
1978 Volume 26 Issue 9 Pages
2671-2673
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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Four phenolic compounds were isolated from the leaf oil of Illicium anisatum L. Spectroscopic and synthetic studies showed that they were 1-allyl-2-methoxy-4, 5-methylenedioxybenzene (I), 4-allyl-2, 6-dimethoxyphenol (II), 1-allyl-3-methoxy-4-(3-methylbut-2-enyloxy) benzene (III) and 1-allyl-3, 5-dimethoxy-4-(3-methylbut-2-enyloxy) benzene (IV). Of the four, III and IV were new compounds.
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HIDEMI ISHII, YOSHIO NAKAGAWA, TETSUYA SUGA, SHINKICHI NIINOBE
1978 Volume 26 Issue 9 Pages
2674-2678
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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In this paper, the mechanism of inhibition by aminotriazole (3-amino-1, 2, 4-triazole) of fatty acid synthesis was studied with cell free system of the ratliver. The concentration of this compound in the liver was 20 mM at 30 min after the injection of the compound (100 mg/100 g, i.p.). About 80% of this compound in the liver cell was recovered in the supernatant fraction (cytoplasm) by subcellular fractionation of the liver homogenate. In the experiment of cell free system, the incorporations of
14C-acetate and
14C-acetyl-CoA into fatty acid were inhibited about 50% by the addition of 20 mM aminotriazole into the system and this inhibition depended on the concentration of the compound. However, the incorporation of
14C-malonyl-CoA into fatty acid was not inhibited by aminotriazole. Aminotriazole repressed the activation and stabilization of acetyl-CoA carboxylase in the rat liver by citrate and inhibited this enzyme non-competitively.
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AKIRA ITO, KENJI KITAMURA, HISAE ISHII, YO MORI
1978 Volume 26 Issue 9 Pages
2679-2683
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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Dipeptidase activity was determined in rat carrageenin granuloma as a chronic inflammation model. The specific activity of dipeptidase in the granulation tissue was about 230 and 40 times higher than those in the exudate and in the serum, respectively. Most part of this activity was distributed in the soluble fraction. The dipeptidase partially purified was most active in the pH range 8.1 to 9.3 and preferentially hydrolyzed dipeptides, such as Gly-L-Leu, L-Val-L-Leu, L-Leu-L-Ala, L-Val-L-Phe and L-Leu-L-Len. This enzyme, however, did not split dipeptides containing C-or N-terminal L-proline, tripeptides, L-leucineamide, L-leucine-p-nitroanilide and hippuryl-L-Phe. After injection of carrageenin, the dipeptidase activity in the granulation tissue increased gradually and reached a maximum level on the 15th day.
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KIMIKO AOKI, YUKIO KUROIWA
1978 Volume 26 Issue 9 Pages
2684-2688
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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Liquid chromatography with o-phthalaldehyde as a fluorogenic reagent and sodium citrate as an elution buffer was applied to the assay of taurine, aspartic acid, glutamic acid, glycine, and γ-aminobutyric acid in the rat brain. These amino acids were quantified at picomol level. This sensitive assay procedure and microdissection technique of Palkovits were used to measure their content in the substantia nigra and cerebral cortex in the brain of rats killed by decapitation or microwave exposure.
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KOTARO TAKAHASHI, MASAKO TAKANI
1978 Volume 26 Issue 9 Pages
2689-2693
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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A new tetrahydroxy triterpene acid, named clethric acid (I), in addition to barbinervicand rotundic-acids, has been isolated from the leaves of Clethra barbinervis SIEB. et ZUCC and clethric acid was elucidated as 3α, 19α, 23, 24-tetrahydroxyurs-12-en-28-oic acid by the chemical and spectral evidences. The
13C-nuclear magnetic resonance spectra of the methylates and acetyl methylates of clethric acid, pomolic acid, rotundic acid and barbinervic acid were studied.
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HIDEKO KAWAKI, HIDEAKI FUJIWARA, YOSHIO SASAKI
1978 Volume 26 Issue 9 Pages
2694-2697
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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From the two step equilibria of the complex formation between the shift reagent Eu (DPM)
3 and a large excess of aliphatic alcohol, the two complex shifts Δ
1, Δ
2 and equilibrium constants K
1, K
2 are estimated. Δ
1 and K
1 are comparable with Δ
c and K
c obtained in an equimolar condition, and the magnitudes of K
2 are included within the errors of K
1. The infinite concentration shift Δ
ic obtained in the presence of a large excess of the donor is also comparable with Δ
1. These results suggest the role of the solvent molecule occupying an overwhelming majority in the sample solution, where the molecular interaction is a time-averaging 1 : 1 donor-acceptor collision in the nuclear magnetic resonance time scale.
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YUKIO KAMEDA, TETSU HASE, SHOICHI KANATOMO, YOKO KITA
1978 Volume 26 Issue 9 Pages
2698-2704
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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AAA 6029 (Pseudomonas sp.) was isolated from soil by using the synthetic medium containing N-benzoyl-D-phenylalanine as a sole source of carbon. The bacteria produce a D-acylase which hydrolyzes N-acyl-D-amino acids. The D-acylase was extracted by means of sonic oscillation and purified by ammonium sulfate fractionation, DEAE cellulose chromatography, and Sephadex G-100 gelfiltration. The purified enzyme was represented about 900 fold purification over the cell free extract. The molecular weight of this enzyme was estimated to be about 45000 by gelfiltration. This enzyme can hydrolyze N-benzoyl and N-acetyl derivatives of the D-form of phenylalanine, methionine, leucine, alanine, and valine. But the acylase can not hydrolyze N-acyl derivatives of L-amino acids.
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KAZUMI DANJO, AKINOBU OTSUKA
1978 Volume 26 Issue 9 Pages
2705-2709
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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The compaction behavior and adhesive properties of original and surface-modified quartz powders were examined under various conditions of relative humidity. Adhesive force at a contact point (H) decreased with the progress of surface modification in the whole region of the relative humidity. H falls at small water contents and shows a minimum when the amount of adsorbed water is close to that required to monolayer complection (V
m). The patterns of the porosity of powder bed (s) in a centrifugal field as a function of adsorbed water showed a striking resemblance to those for the adhesion force at a contact point. Finally, the relationship among H, s and the average force acting on a particle (F) was examined. A fairly good correlation was observed between log (s-0.26) and log (H/F), regardless of the degree of surface modification.
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YUKIO KAMEDA, TETSU HASE, SHOICHI KANATOMO, KEIKO MIYAZAKI
1978 Volume 26 Issue 9 Pages
2710-2717
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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Screening experiment in soil bacteria have been carried out for the purpose of finding out new acylases. As a result, AAA 6020 (Pseudomonas sp.) which produces a new acylase (tentatively called phenylacetyl-DL-acylase) was isolated. AAA 6020 was incubated in the synthetic medium containing of phenylacetyl-D-leucine and the bacterial cells were harvested. The phenylacetyl-DL-acylase was extracted from AAA 6020 by means of sonic oscillation and purified by ammonium sulfate fractionation, DEAE cellulose chromatography and Sephadex G-200 gelfiltration. The purified enzyme was represented about 29 fold purification over the cell free extract and the specific activity toward N-phenylacetyl-D-leucine was 124 units/mg. The homogeneity of purified enzyme was demonstrated by means of disc electrophoresis and analytical ultracentrifugation. A molecular weight of the enzyme was estimated to be about 115000 by gelfiltration. The optimal pH toward N-phenylacetyl-D-leucine was 8.0. This enzyme hydrolysed not only N-phenylacetyl-D-amino acids but also N-phenylacetyl-L-amino acids. However N-benzoyl and N-acetyl derivatives of D- and L-amino acids were not hydrolyzed. Thus this DL-acylase has specificity toward phenyl-acetyl-amino acids but has not optical specificity.
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MASAYUKI MUROI, TOYOKAZU KISHI
1978 Volume 26 Issue 9 Pages
2718-2722
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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Epoxidation of 18-dihydroleucomycin A
s (5) with m-chloroperbenzoic acid afforded 18-dihydromaridomycin II (6). Conversion of leucomycin A
s (1) into maridomycin II (2) was also accomplished in a similar process. This evidence together with the result of X-ray analysis of 9-propionylmaridomycin III has finally confirmed the absolute stereochemistry of leucomycin A
s. In addition, Δ
2-9-epi-18-dihydromaridomycin III (12) was prepared by the NaBH
4 reduction of 9-dehydromaridomycin III (11) and the effect of the C-9 hydroxyl group on optical rotations was discussed.
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SUMIE YOSHIOKA, HIROYASU OGATA, TOSHIO SHIBAZAKI, AKIRA EJIMA
1978 Volume 26 Issue 9 Pages
2723-2728
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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The kinetics of the copper (II) ion catalyzed oxidation of sulpyrine by molecular oxygen was investigated. Sulpyrine was hydrolyzed to 4-methylaminoantipyrine (MAA) and then MAA was oxidized to antipyrinyl-4-peroxide (AP) via 4-aminoantipyrine (AA), and hydroxymethanesulfonate formed in the hydrolysis is not effective on the rate of the oxidation of MAA. Below pH 4 the oxidation of MAA to AP was the rate-determining step. On the other hand above pH 5 the hydrolysis of sulpyrine to MAA was the rate-determining step. The rate constants of the oxidative reactions of MAA to AA, and of AA to AP could not be determined because of the difficulties of determining the reaction orders. The complexation of MAA and AA with copper (II) ion and molecular oxygen was suggested from the observation that the both reactions were of first order with respect to copper (II) ion and of 0.5 order with respect to molecular oxygen.
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HIROAKI TAKAYANAGI, HARUO OGURA, YOICHI IITAKA
1978 Volume 26 Issue 9 Pages
2729-2733
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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The crystal structure of monochlorosantonin, C
15H
17CIO
3 has been determined in order to elucidate the molecular structure. The crystals are orthorhombic with space group P2
12
12
1 and the unit-cell dimensions are a=11.180Å, b=13.894Å, c=9.211Å, Z=4. The crystal structure was solved by the heavy-atom method and the atomic parameters were refined to a final R value of 0.076 for 842 reflexions. From the analytical data the compound was confirmed to be 14-chlorosantonin (I).
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NOBUYOSHI KANENIWA, AKIKO IKEKAWA, MASAHIRO SUMI
1978 Volume 26 Issue 9 Pages
2734-2743
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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Amobarbital was ball-milled, triturated, mortar-ground or stamp-milled in the absence or in the presence of various kinds of the diluents, and influence of the mechanical treatment on the physical and chemical state of amobarbital powders was investigated. Intensity of the signals of amobarbital in the X-ray diffraction diagram decreased by the mechanical treatment. The signal of amobarbital in the DTA thermogram was not influenced by the mechanical treatment in the absence of the diluent. But the signal branched off into more than two signals, shifted to the lower temperature, decreased in intensity and disappeared by the mechanical treatment in the presence of the diluents. These phenomena were influenced more remarkably by the kind of the diluents than by the kind of the mechanical treatment. These tendencies were remarkable in the presence of precipitated silica, carbon black, granules of activated charcoal or ethyl cellulose and for the mixtures containing small amount of amobarbital. Roughly speaking, the decrease in the melting point of amobarbital in the mechanically treated mixture was remarkable, when the intensity of the signals of amobarbital in the X-ray diffraction diagram decreased markedly. It was suggested from the infrared spectra and the electron spin resonance spectra of various kinds of the samples that the interaction was caused between amobarbital and the diluent by the mechanical treatment.
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NOBUYOSHI KANENIWA, AKIKO IKEKAWA, MASAHIRO SUMI
1978 Volume 26 Issue 9 Pages
2744-2758
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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Amobarbital was ball-milled, triturated, mortar-ground or stamp-milled in the absence or in the presence of various kinds of diluents, and the variation of solubility of amobarbital from these samples in the KH
2PO
4-Na
2HPO
4 buffer solution of pH of 6.0 at 30°was investigated. It was suggested from the results of the elemental analysis, measurement of the mass spectra and the infrared spectra, and the chemical analysis by thin-layer chromatography and gas chromatography that amobarbital in the mechanically treated mixtures of precipitated silica or carbon black was hydrolyzed by the addition of water. It was also suggested that amobarbital decomposed or formed complex by ball-milling in the presence of potato starch. But, it was considered that decomposition of amobarbital by the mechanical treatment in the absence and in the presence of the other diluents was negligible. Solubility of amobarbital in the buffer solution increased by mechanical treatment in the presence of methyl cellulose or hydroxypropyl cellulose. It was considered that solubilization of amobarbital was related to the decrease in the intensity of the signals of amobarbital in the X-ray diffraction diagrams and dropping of the melting point of amobarbital by mechanical treatment in the presence of the diluent. It was also considered that solubilization of amobarbital was due to the interaction with the diluent in the suspension caused by mechanical treatment and to the kind of the crystal structure of amobarbital formed by recrystalization after dissolution.
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HIROSHI YAMANAKA, HIROSHI EGAWA, TAKAO SAKAMOTO
1978 Volume 26 Issue 9 Pages
2759-2764
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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In order to introduce a carbon function to the 2-position of quinoline, the reaction of quinoline 1-oxide with some isoxazole derivatives whose 4-positions are free, was investigated. The products, such as 2-(5-amino-3-methyl-4-isoxazolyl)-, 2-(5-ethylamino-3-methyl-4-isoxazolyl)-, 2-(5-hydroxy-3-methyl-4-isoxazolyl)-, and 2-(5-ethoxy-3-methyl-4-isoxazolyl)-quinolines were hydrogenated in the presence of Raney nickel catalyst to give the quinoline derivatives possessing the desired side chains. Treatment of 2-(5-hydroxy-3-methyl-4-isoxazolyl) quinoline with excess phosphoryl chloride afforded 2-(5-chloro-3-methyl-4-isoxazolyl) quinoline whose chlorine atom could be substituted by diethylamine and ethoxide ion. These reactions were equally applied to isoquinoline 2-oxide yielding the corresponding products.
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TADAKAZU TSUJI, YOSHIMI OTSUKA
1978 Volume 26 Issue 9 Pages
2765-2767
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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3-Amino-6-methyluracil and its thio analogs were synthesized. From these thio analogs, 7-methyl-5H-1, 3, 4-thiadiazolo [3, 2-α] pyrimidin-5-one, its 2-amino and 2- or 5-thio derivatives were prepared. Reflux of thiadiazolopyrimidines with chloroacetic acid or hydrochloric acid led to the ring opening of the thiadiazole moiety to give unexpected 3-amino-6-methyluracil.
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MASASHI TOMODA, NORIKO SATOH, CHIEKO OHMORI
1978 Volume 26 Issue 9 Pages
2768-2773
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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A mucous polysaccharide, named Lilium-Lo-glucomannan, has been isolated from the bulbs of Lilium longiflorum THUNB. It was homogeneous on glass-fiber paper electrophoresis and in ultracentrifugal analysis. The component sugars of it were D-mannose and D-glucose in the molar ratio of 5 : 2, and its molecular weight was estimated at 263000. Methylation, periodate oxidation, and partial acetolysis studies suggested that the polysaccharide is mainly composed of β-1→4 linked aldohexopyranose residues and it contains about ten aldohexose units per non-reducing terminal group on the average. D-Mannose units occupy non-reducing terminal positions and branch points linked through positions 2 or 3. The O-acetyl groups in the polysaccharide were identified and determined as the content of 3.2%. They were located in positions 6, 2, 6, 3, 6, and 2, 3, 6 of a part of D-mannose units, and 6 and 2, 3, 6 of a part of D-glucose units.
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TAKAHARU MIZUTANI, KAZUKO WATANABE, REIKO SHIMIZU, POFENG KUO, AKIRA M ...
1978 Volume 26 Issue 9 Pages
2774-2781
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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An active core in a limited chymotryptic digest of a bovine parotid hypocalcemic substance was purified and some properties of that core were investigated. After digestion of hypocalcemic protein (400 mg) for 2 hr with chymotrypsin (8 mg) at 37°, the mixture (20 ml) was chromatographed at 4°on a column of Sephadex G-100 (4×70 cm) and the fraction eluted at Kav 0.2 was obtained. The fraction was active on hypocalcemic activity and further rechromatographed on Sepharose 6B in 6M guanidine hydrochloride (Gdn-HCl)-0.1M Tris-HCl at pH 8.0. Major fraction on rechromatography (Kd 0.49) was purified by preparative disc electrophoresis and the purified protein (CPD-P) was active in a dose of 0.06 mg/kg (Ca lowering rate 6.5±1.1%). Molecular weight of CPD-P was 11000 by sodium dodecyl sulfate gel (20%) electrophoresis and 12500 by gel chromatography in 6M Gdn-HCl. The amino-terminal sequence of CPD-P was Lys-Leu-identical to that of native hypocalcemic protein and the carboxyl-terminal amino acid was phenylalanine. Amino acid composition of CPD-P was shown and secondary structure of CPD-P was composed of α-helix (90%) by the measurement of CD spectrum.
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HARUO OGURA, KIMIO FURUHATA, HIROSHI TAKAHASHI, YOICHI IITAKA
1978 Volume 26 Issue 9 Pages
2782-2787
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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In order to determine the absolute configuration of product from a reaction of sugar lactone and lithiated heterocycles, and X-ray crystal structural analysis of 1-(1, 3-dithian-2-yl)-2, 3 : 5, 6-di-O-isopropylidene-β-L-gulofuranose was carried out. This compound was prepared from 2, 3 : 5, 6-di-O-isopropylidene-L-gulono-1, 4-lactone and lithiated 1, 3-dithiane. The crystals are monoclinic with space group P2
1 and unit cell dimensions of a=18.566 (7) Å, b=9.544 (2) Å, c=6.462 (1) Å, β=91.68 (3)°, z=2. The X-ray analysis was carried out with the heavy-atom method and refined by the block-diagonal least-squares method including anisotropic thermal parameters, and the final R value was 0.071. In conclusion, the absolute configuration of the anomeric position was determined to be R chirality.
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TAIJU KURAMOTO, NAOKO MATSUMOTO, TAKAHIKO HOSHITA
1978 Volume 26 Issue 9 Pages
2788-2792
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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The syntheses of four new bile alcohols, 5β-cholestane-3α, 7α, 12α, 22α-tetrol, 5β-cholestane-3α, 7α, 12α, 22β-tetrol, 5β-cholestane-3α, 7α, 12α, 23α-tetrol, and 5β-cholestane-3α, 7α, 12α, 23β-tetrol, were described. The 22-hydroxy compounds were prepared from bisnorcholyl aldehyde by the Grignard reaction with 3-methylbutylmagnesium chloride. The 23-hydroxy compounds were prepared from norcholic acid by the condensation with diisobutylcadmium and the subsequent lithium aluminum hydride reduction of the resulting 3α, 7α, 12α-trihydroxy-5β-cholestan-23-one. One of the synthetic tetrols, 5β-cholestane-3α, 7α, 12α, 23β-tetrol was identical with a bile alcohol isolated from a patient with cerebrotendinous xanthomatosis.
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SUSUMU KITAGAWA, HISASHI TANAKA
1978 Volume 26 Issue 9 Pages
2793-2798
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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Novel dithio ligands, N-(2-methylphenyl)- and N-(2, 6-dimethylphenyl)-β-mercaptothiocinnamamide were synthesized and their pK
a values in 10% EtOH aqueous solution were determined spectrophotometrically to be 3.15±0.03 and 3.14±0.04, respectively. Bis {N-(2-methylphenyl)- and bis {N-(2, 6-dimethylphenyl)-β-mercaptothiocinnamamido}-Pd (II) were prepared and their interaction with pyridine were examined. It was observed that both complexes were capable of forming their pyridine clathrates bis {N-(2-methylphenyl)- and bis {N-(2, 6-dimethylphenyl)-β-mercaptothiocinnamamido} Pd (II) bipyridine by recrystallization from their pyridine solution. These pyridine molecules were supposed to interact with the thioamido protons of the ligands.
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TOSHIO KAMEI, YOSHIKO TAKIGUCHI, HAJIME SUZUKI, MEIKI MATSUZAKI, SHOSH ...
1978 Volume 26 Issue 9 Pages
2799-2804
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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Cholesterol could be used to adsorb the 3β-hydroxysteroid oxidase of Streptomyces violascens origin from a crude enzyme solution, and the adsorbed enzyme could be eluted with a suitable detergent such as Triton X-100. The enzyme was purified by ammonium sulfate precipitation and affinity chromatography on cholesterol with a recovery of 79% from the culture filtrate. The purified enzyme was detected as a single band on SDS-polyacrylamide gel electrophoresis. The molecular weight of the enzyme was 61000 by SDS-polyacrylamide gel electrophoresis. The purified enzyme exhibited a characteristic spectrum of flavoenzyme. The flavin moiety of the enzyme was isolated and identified as flavin adenine dinucleotide.
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MASAHIRO NAGAI, MASAYOSHI KUBO, MASAO FUJITA, TAKAO INOUE, MITSUYOSHI ...
1978 Volume 26 Issue 9 Pages
2805-2810
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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The structure of aceroside I, C
25H
32O
8, mp 170-171°(acetone), [α]
20D-7.7°, which was isolated from the stem bark of Acer nikoense MAXIM. (Aceraceae), was established to be acerogenin A β-D-glucopyranoside represented by formula 1. Acerogenin A, C
19H
22O
3, mp 151-152°, [α]
20D+57.3°, was concluded to be a m-, p'-bridged diphenyl ether type diarylheptanoid (2) on the basis of chemical and spectroscopic (especially NMR) evidences. The stereostructure of 2 was determined by derivation of acerogenin A (2) into (S)-1-(p-hydroxyphenyl)-7-(p-methoxyphenyl)-heptan-3-ol. Acerogenin A (2) is the first example of a novel type of diarylheptanoid-20-oxa-[7, 1]-metapara-cyclophane.
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MIKIO HORI, TADASHI KATAOKA, HIROSHI SHIMIZU, KAZUHIRO ONOGI
1978 Volume 26 Issue 9 Pages
2811-2818
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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Reactions of sulfides with SbCl
5 or perchloric acid were examined. Sulfoxides having no α-hydrogens produced very stable 1 : 1 adducts of them and SbCl
5. On the other hand, sulfoxides having α-hydrogens formed the intermediates of sulfonium or carbonium ion. In the reactions of benzyl phenyl sulfoxide (12) and 11-phenyl-6, 11-dihydrodibenzo-[b, e] thiepin 5-oxide (21a) the intermediates reacted with MeONa to give sulfides substituted by a methoxy group at α-position. A novel transannular reaction and an intramolecular 1, 2-rearrangement of the intermediate were found in the reaction of 11-phenyl-6, 11-dihydrodibenzo [b, e] thiepin-11-ol 5-oxide (26) or 11-methoxy-11-phenyl-6, 11-dihydrodibenzo [b, e] thiepin 5-oxide (34). The bridged sulfonium intermediate (32) was isolated in good yield from the reaction of 26 or 34 with perchloric acid. The mechanism of the reactions was discussed.
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HISAO SONE, MASAHARU KOJIMA
1978 Volume 26 Issue 9 Pages
2819-2823
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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anti-6α- and anti-6β-Hydroxycortisol 6-hemisuccinate-BSA antisera (anti-F-6α-HS and anti-F-6β-HS) were obtained by immunizing rabbits. The specificity of each antiserum was assessed by determining the cross-reactivities with 37 kinds of steroids and was compared with that of anti-cortisol 21-hemisuccinate-BSA conjugate antiserum (anti-F-21-HS). anti-F-6β-HS had higher specificity than that of anti-F-6α-HS for the steroids structurally different to cortisol in ring A. anti-F-21-HS had an obviously lower specificity than those of anti-F-6α-HS and anti-F-6β-HS for the steroids differing structurally from cortisol only in the 17-side chain.
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HISAO TOMIDA, TOSHIHISA YOTSUYANAGI, KEN IKEDA
1978 Volume 26 Issue 9 Pages
2824-2831
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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The solubilization of 34 benzoic acid derivatives by polyoxyethylene lauryl ether micelles was quantitatively studied by solubility measurement and equilibrium dialysis. The logarithms of partition coefficients (K) of solubilizates between aqueous and micellar phases were directly related to the logarithms of their partition coefficients between aqueous solution and n-octanol (P
oetanol). The plots could be grouped in four parallel linear relationships, each of which was characterized by the intercept b value. When the b value is connected with the positional distribution of hydrophilicity of the palisade layer with reference to n-octanol water content, the physical meaning of the value is probably related to the site of incorporation of solutes within the polyoxyethylene mantle. The results show that benzoic acid derivatives examined are classified into dicarboxylic acids, nitro and cyano compounds, the majority of compounds, and salicylic acids group, which are located in order from the outer layer of the mantle toward the hydrocarbon core.
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HISAO TOMIDA, TOSHIHISA YOTSUYANAGI, KEN IKEDA
1978 Volume 26 Issue 9 Pages
2832-2837
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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As a further approach to an understanding of a relationship between the magnitudes of micellar solubilization and the hydrophobicities of solubilizates, steroid hormones (19 species) were selected to explore the meaning of the intercept b value. Two linear free energy relationships were established between the aqueous-polyoxyethylene lauryl ether micellar partition coefficient (K) and the partition coefficient (P
octanol) between aqueous solution and n-octanol. One consisted of the steroids carrying a fluorine atom at a carbon 9 and the other of those carrying no fluorine atom. The b value predicted that the fluorine steroids are solubilized in the outer layer of the mantle while the others are incorporated into rather inner position, which was consistent with the experimental results.
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PRITAM SINGH, YOSHIHISA MIWA, JUTARO OKADA
1978 Volume 26 Issue 9 Pages
2838-2843
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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The kinetics and mechanism of vapor-phase ammoxidation of furfural to 2-furonitrile, and of 2-thiophenealdehyde to 2-thiophenenitrile, were studied over the Mo-Bi-Sb catalyst (molar ratio 3 : 5 : 2) in an integral flow fixed bed reactor under atmospheric pressure. The reaction temperature was 390°for furfural and 400°for 2-thiophenealdehyde. In both cases, the selectivity of nitrile was maximum with high conversion of aldehyde and the by-products formed were negligible in amounts. The reaction rate depended on the partial pressure of aldehyde and oxygen, but unaffected by that of ammonia. Model fitting was tried by the non-linear least square method, and the experimental data were well interpreted by the Langmuir-Hinshelwood mechanism, where the rate controlling step was the surface reaction between adsorbed aldehyde molecules and adsorbed oxygen molecules.
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MASAHIRO IKEHARA, YASUO SHIBATA, TOKUHIKO HIGASHI, SYUICHI SANADA, JUN ...
1978 Volume 26 Issue 9 Pages
2844-2849
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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Rats fed on high-fat diet showed a higher level of cholesterol in liver and a lower incorporation of
14C-acetate into liver cholesterol. The activity of HMG-CoA reductase, which is a key enzyme in cholesterol biosynthesis, was repressed in those rats. Ginsenoside-Rb
1 purified from Ginseng (the root of Panax ginseng C.A. MEYER) has been found to reverse such effect of high-fat diet when administered on earlier days of feeding.
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FUJIO KAMETANI, HIROSHI TERADA, IKUKO KONO, JUNKO TAKEDA
1978 Volume 26 Issue 9 Pages
2850-2854
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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Binding affinity of 2-benzenesulfonamide-5-(β-methoxyethoxy)-pyrimidine (GL) to bovine serum albumin (BSA) was investigated by equilibrium dialysis and fluorescence titration. Binding parameters of GL to BSA was calculated from the results of equilibrium dialysis assuming two classes of binding sites on BSA. The values for n
1, n
2 and k
1, k
2 were 0.109, 2.47 and 3.71×10
5M
-1, 4.78×10
3M
-1, respectively. The association constant of GL which was obtained by fluorescence titration would be the secondary association constant calculated from the results of equilibrium dialysis.
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TEISUKE OKANO, MAKOTO HAGA, KUNIO UJIIE, NOBORU MOTOHASHI
1978 Volume 26 Issue 9 Pages
2855-2859
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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Half-wave reduction potential and half-peak oxidation potential have been measured for 11 methyl-substituted benz [c] acridines and unsubstituted benz [c] acridine in acetonitrile with tetraethylammonium perchlorate electrolyte. A linear correlation was obtained between the energy of the lowest unoccupied molecular orbital calculated by LCAO-SCF method and the half-wave reduction potential, and also between the energy of the highest occupied molecular orbital and the half-peak oxidation potential. The correlations between carcinogenic activity and both half-wave oxidation and reduction potentials were interpreted in connection with the electron charge density of the K-region. The results of LCAO-SCF calculation for the electron charge density and the electrophilic superdelocalizability index indicated that the electrophilic reactivity of the K-region or the ring nitrogen atom of methyl-substituted benz [c] acridines may be essential for their carcinogenic activity.
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SEIKI TANADA, KEITO BOKI, TAKAMICHI TAMURA, YOSHIHIRO HORI, KAZUOKI MA ...
1978 Volume 26 Issue 9 Pages
2860-2865
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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Adsorption equilibria of trimethylamine as the offensive odor substance was measured by a gravimetric method to elucidate the mechanism of its adsorption on activated carbon, silicate, and zeolite. The mechanism of adsorption was discussed on the basis of application of the Dubinin-Astakhov equation to the adsorption isotherms and relation between the characteristic energy (E), exponent (n) and pore size distribution. The Dubinin-Astakhov equation was well applicable to the adsorption isotherms of activated carbon, silicate, and zeolite. The exponent (n) of activated carbon, silicate, and zeolite was 2, 3, and 3, respectively. It was confirmed that the adsorption of trimethylamine on the adsorbents resulted in the volume filling of their micropores by the mechanism of capillary condensation, and that the two or three degrees of freedom in translation of trimethylamine was lost by its adsorption on the micropores or ultramicropores, respectively. The amount of trimethylamine adsorbed on the microporous adsorbents was determined by their micropore volume of pore radius less than about 20 Å.
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YASUMITSU TAMURA, MOONWOO CHUN, HIROSHI NISHIDA, SUNDO KWON, MASAZUMI ...
1978 Volume 26 Issue 9 Pages
2866-2873
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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Several new 3-azidoindolenines have been synthesized in high yields (i) by the reaction of 2, 3-disubstituted indoles with iodine azide or bromine azide, and (ii) by the reaction of 3-chloroindolenines with sodium azide in acetic acid. The 3-azidoindolenines undergo thermal rearrangement in variable yields and ratios to quinoxalines and quinazolines, along with the formation of the parent indoles. The ring-expansion of 3-azido-2, 3-diphenylindolenine to 2, 3-diphenylquinoxaline also occurs on treatment with acid but in much lower yield. Photolysis of the 3-azidoindolenines gives the parent indoles as major products.
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YASUMITSU TAMURA, MOONWOO CHUN, KAZUNORI OHNO, SUNDO KWON, MASAZUMI IK ...
1978 Volume 26 Issue 9 Pages
2874-2879
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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Several 3-substituted 2-azidomethylindoles have been synthesized in high yields either by the reaction of 3-substituted 2-alkylindoles with iodine azide in dry acetonitrile or by treatment of 3-substituted 2-alkyl-3-chloroindolenines with sodium azide in acetic acid. 1, 3-Dipolar cycloaddition of the 2-azidomethylindoles with dimethyl acetylenedicarboxylate gives 2-triazolylmethylindole derivatives. Ozonolysis of 3-phenyl-2-azidomethylindoles in acetic acid gives 2-azidoacetamidobenzophenones, which cyclize to 1, 4-benzodiazepines by treating with triphenylphosphine in toluene at room temperature and then refluxing.
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TAKASHI TSUCHIYA, HARUKI SASHIDA, HIROYUKI SAWANISHI
1978 Volume 26 Issue 9 Pages
2880-2885
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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The thermolysis of the N-ethoxycarbonylimino-1, 2, 5, 6-tetrahydropyridinium ylides (8), which were prepared from the corresponding parent N-ethoxycarbonyliminopyridinium ylides (10) by successive sodium borohydride reduction and methylation with methyl iodide, gave the [2, 3] rearrangement products, 3-vinyltetrahydropyrazoles (15), and the elimination products, pentadienylhydrazines (16). In contrast, the thermolysis of the pyrrolinium ylide (9), which was prepared from N-methyl-Δ
3-pyrroline by N-amination and ethoxycarbonylation, gave the [1, 2] rearrangement product, tetrahydropyridazine derivative (18), and did not give the [2, 3] rearrangement product (20).
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TADAO FUJITA, HIROKO MASUNO, TAKEICHI SAKAGUCHI
1978 Volume 26 Issue 9 Pages
2886-2889
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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Mixed ligand complexes containing uracil and 6-methyluracil were prepared. The complexation and coordination sites of the mixed ligand complexes, Cu (II) (GG) (UraH)HBr·3/2H
2O and Cu(II) (GG) (6-MeuraH) HBr·H
2O, were discussed. It is suggested that the nitrogen atom N1 of uracil bases is the coordination site and that glycylglycine behaves as a tridentate chelate.
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MICHIHIKO MIYAZAKI, TAKEO IWAKUMA, TADASU TANAKA
1978 Volume 26 Issue 9 Pages
2889-2893
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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Major metabolites of the antianginal drug, Diltiazem, 3 (S)-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2, 3-dihydro-2(S)-(4-methoxyphenyl)-1, 5-benzothiazepin-4(5H)-one, have been synthesized. In connection with these metabolites, several S- and N-oxides were prepared.
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TATSUO YAMAUCHI, FUMIKO ABE, MASATOSHI NISHI
1978 Volume 26 Issue 9 Pages
2894-2896
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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^<13>C-Chemical shifts were obtained on 5α-cardenolides, including uzarigenin and its C-19-, C-11β-, C-15α-hydroxyl-, and Δ
14- and Δ
8(14)-anhydro-derivatives.
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NORIHIDE UMINO, TAKEO IWAKUMA, MUNEYOSHI IKEZAKI, NOBUO ITOH
1978 Volume 26 Issue 9 Pages
2897-2898
Published: September 25, 1978
Released on J-STAGE: March 31, 2008
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Sodium acyloxyborohydrides, [NaBH
3 (OCOR)], prepared from an equivalent mol sodium borohydride and various carboxylic acids in tetrahydrofuran reduced oxime ethers to the corresponding amines. Particularly sodium trifluoroacetoxyborohydride gave best results.
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