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Volume 26, Issue 6
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SUSUMU KITAGAWA, HISASHI TANAKA1978 Volume 26 Issue 6 Pages 1629-1632
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBis (N-phenyl-β-mercaptothiocinnamamido) Ni (II) was synthesized and its properties were examined. This complex decomposed gradually in pyridine to 3-phenyl-5-phenyl-imino-1, 2-dithiol, while the corresponding palladium complex never decomposed in pyridine and produced its pyridine clathrate. These differences seemed to be caused by the "soft" and "hard" character of the metal ions.View full abstractDownload PDF (505K) -
MICHIHIRO YAMAMOTO, SHIGEHO INABA, HISAO YAMAMOTO1978 Volume 26 Issue 6 Pages 1633-1651
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of 2-trihaloacetamidophenyl ketones was prepared. The 2-trichloro- or 2-tribromoacetamidophenyl ketones, in most cases, were readily converted to the corresponding 4-substituted 2 (1H)-quinazolinones by reaction with ammonia via loss of the trihalomethyl function. Treatment of 5-chloro-2-trichloroacetamidobenzophenone with ammonium acetate in dimethyl sulfoxide (method H) gave 6-chloro-4-phenyl-2 (1H)-quinazolinone in quantitative yield, whereas, under similar conditions, the 2-trifluoroacetamide derivative reacted to yield 6-chloro-4-phenyl-2-trifluoromethylquinazoline. In the case of the N-substituted derivative of 2-trichloroacetamidobenzophenones, the 4-phenyl-2H-3, 1-benzoxazin-2-ones or 2-aminobenzophenone imines were isolated depending on the reaction conditions. For the conversion of the N-substituted derivatives to the corresponding 2 (1H)-quinazolinones the best result was obtained by heating them with ammonium acetate in dioxane (method J). In the case of the trichloroacetanilides bearing an ethoxycarbonyl, cyano or hydrogen in the o-position, the corresponding cyclic or acyclic ureas were obtained by this reaction. Mechanisms for their formations are proposed.View full abstractDownload PDF (1921K) -
YOSHIHARU MACHIDA, TSUNEJI NAGAI1978 Volume 26 Issue 6 Pages 1652-1658
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIntending to explore a new peroral controlled release dosage form using hydroxypropyl cellulose (HPC), an investigation was made on the disintegration and dissolution property of directly compressed tablets of dl-isoproterenol hydrochloride (IPH) held in a simple (PM) or spray dried (SDM) mixtures of HPC and lactose. A commercially available prolonged action preparation of IPH was also examined in comparison with the above preparations. The hardness and disintegration time (dissolution time in the case of SDM tablet) increased with an increase in HPC. SDM was superior in molding property, but the tablet dissolved rapidly compared with PM tablet. A double layer tablet of IPH held in 200 mg of SDM as the initial phase and 300 mg of PM as the depot phase afforded a suitable sustained release property without taking a strikingly rapid dissolution upon changing from No. 1 medium (acidic) to No. 2 (neutral), while the commercially available prolonged action preparation showed a rapid dissolution upon such the change of dissolution media. This sustained release property could be controlled by adjusting the ratio of the active ingredient in the respective layers. Accordingly, this double layer tablet seemed to be applicable to peroral prolonged action dosage forms on the basis of the consideration regarding the absorption, elimination and other properties of the active ingredient.View full abstractDownload PDF (805K) -
TAKASHI ABE1978 Volume 26 Issue 6 Pages 1659-1665
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSince there are few reports dealing with the barrier efficiency of normal skin during childhood, in vivo experiments were carried out on 40 healthy Japanese children of both sexes aged between 3 to 12 years. Two important parameters for barrier properties : transepidermal water loss (TWL) value and the skin surface lipid value, were measured by the original methods devised during the course of our studies. Statistical analysis was employed to understand interrelations between those two parameters. The results revealed the following characteristic barrier properties of child skin surface. 1) Inverse correlations were found between TWL values and total lipid values in the forearm skin. Analogous correlations were also observed between TWL values and cholesterol values. However, there were no correlations between TWL values and squalene values. 2) The amount of cholesterol was significantly higher than the amount of squalene. 3) No statistical significance with respect to age, sex or weight of the children and the observed TWL, total lipid, squalene or cholesterol values was found in this study. 4) TWL measurements suggested that the barrier efficiency of the stratum corneum of child skin is nearly the same as that for adult skin as previously reported. 5) It was confirmed that the amount of total lipids or squalene is significantly smaller and the cholesterol amount slightly higher in children than in adults.View full abstractDownload PDF (724K) -
MINEO SHIMIZU, KENICHI SHINGYOUCHI, NAOKATA MORITA, HARUHISA KIZU, TSU ...1978 Volume 26 Issue 6 Pages 1666-1671
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour triterpenoid saponins (I-IV), isolated from the root of Pulsatilla cernua, were characterized as follows : I, hederagenin (hederag.) 3-O-α-L-rhamnopyranosyl (rham·pyr)-(1→2)-α-L-arabinopyranoside ; II, 3-O-α-L-rham·pyr (1→2)-α-L-arabinopyranosyl (ara·pyr)-hederag. 28-O-α-L-rham·pyr-(1→4)-β-D-glucopyranosyl (gluc·pyr)-(1→6)-β-D-glucopyranoside ; III, 3-O-α-L-rham·pyr-(1→2)-[β-D-gluc·pyr-(1→4)]-α-L-ara·pyr-hederag. 28-O-α-L-rham·pyr-(1→4)-β-D-gluc·pyr-(1→6)-β-D-glucopyranoside ; IV, hederag. 3-O-α-L-rham·pyr-(1→2)-[β-D-gluc·pyr-(1→4)]-α-L-arabinopyranoside. III and IV are new saponins. II and III were also detected in Pulsatilla koreana and P. chinensis on TLC.View full abstractDownload PDF (690K) -
HITOSHI TAKAI, AKIRA ODANI, YOSHIO SASAKI1978 Volume 26 Issue 6 Pages 1672-1676
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe assignment of 13C nuclear magnetic resonance chemical shifts of 6-substituted quinoline and quinoxaline series were confirmed, and the additivity rules of 13C chemical shifts of 2-substituted naphthalene derivatives were approved for both 6-substituted quinoline and quinoxaline derivatives. The correlation coefficient of meta-like position is promoted by the linear combination of chemical shifts at corresponding meta position of 2-substituted naphthalene derivatives and substituent constants σπ.View full abstractDownload PDF (518K) -
KOTARO TAKAHASHI, SETSUKO MATSUZAWA, MASAKO TAKANI1978 Volume 26 Issue 6 Pages 1677-1681
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMenisdaurin, a new nitrile glucoside was isolated from the vines of Menispermum dauricum DC (Menispermaceae). The structure I, (Z)-6 (S)-(β-D-glucopyranosyloxy)-4 (R)-hydroxy-2-cyclohexene-Δ1, α-acetonitrile has tentatively proposed for menisdaurin and the structure III, (Z)-4 (R)-6 (S)-dihydroxy-2-cyclohexene-Δ1, α-acetic acid γ-lactone for menisdaurilide, the hydrolysis product of menisdaurin, on the basis of the chemical and spectral evidences.View full abstractDownload PDF (591K) -
HIROTERU SAYO, KOICHI MORI, AYAKO UEDA, TAKASHI MICHIDA1978 Volume 26 Issue 6 Pages 1682-1687
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAnodic oxidation of benzenesulfenanilides (4'-OMe (1a), 4'-Me (1b), 4'-Cl (1c), 4'-H (1d)) were investigated by cyclic voltammetry and controlled potential electrolysis at a glassy-carbon anode in acetonitrile. The value of ip/c of the first anodic peak, where ip is the peak current and c is the concentration of 1a, decreased with increase in c, which was ascribed to the hydrolysis of 1a at the surface of the anode caused by the liberation of protons during the electrolysis. Electrolysis of 1a, 1b, and 1c (10 mM) gave the corresponding phenazines, whereas that of 1d did not. The nitrenes are suggested for the formation of the phenazines. Electrolysis of 1a in the presence of water (1%) gave N-phenylthio-p-quinoneimine in addition to 2, 7-dimethoxyphenazine.View full abstractDownload PDF (643K) -
HARUO OGURA, KAZUYOSHI TAKEDA, KOJI KAJIMA1978 Volume 26 Issue 6 Pages 1688-1693
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS6-Isothiocyanatopenicillanate and 7-isothiocyanatodeacetoxycephalosporanate were prepared since they are valuable intermediates in the syntheses of penicillin and cephalosporin derivatives. When the reaction was carried out with those isothiocyanate compounds, addition products with dicyclohexylcarbodiimide were obtained as unexpected by-products. The isothiocyanate derivatives thus obtained were treated with benzylamine to give a penillic acid derivatives.View full abstractDownload PDF (698K) -
SHIUICHI SANADA, JUNZO SHOJI1978 Volume 26 Issue 6 Pages 1694-1697
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe chemical structures of ginsenoside-Rb3 and 20-glucoginsenoside-Rf, which were isolated from Ginseng (the root of Panax ginseng C.A. MEYER ; Araliaceae), were established to be 20S-protopanaxadiol-3-[O-β-D-glucopyranosyl (1→2)-β-D-glucopyranoside]-20-[O-β-D-xylopyranosyl (1→6)-β-D-glucopyranoside] (1) and 20S-protopanaxatriol-6-[O-β-D-glucopyranosyl (1→2)-β-D-glucopyranoside]-20-O-β-D-glucopyranoside (2), respectively.View full abstractDownload PDF (531K) -
KENJI OKAMOTO, SHINICHI SHIMAMURA, HARUAKI YAJIMA1978 Volume 26 Issue 6 Pages 1698-1706
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe docosapeptide, H-Arg-Pro-Ile-Lys-Val-Tyr-Pro-Asn-Ser-Phe-Glu-Asp-Glu-Ser-Val-Glu-Asn-Met-Gly-Pro-Glu-Leu-OH, corresponding to dogfish corticotropin-like intermediate lobe peptide (CLIP), was synthesized using protecting groups removable by hydrogen fluoride.View full abstractDownload PDF (1092K) -
SHIGEO UKAI, TADASHI KIHO, CHIHIRO HARA, KAZUO HIROSE1978 Volume 26 Issue 6 Pages 1707-1712
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA neutral polysaccharide has been isolated from the alkaline extract of the fruit bodies of Tremella fuciformis BERK, which grow in China. It was composed of xylose, mannose, galactose and glucose in molar ratios of 2 : 4 : 5 : 35. Its molecular weight was estimated at 8000, and it showed a positive specific rotation ([α]20D+9° in H2O). The results of periodate oxidation, Smith-type degradation, partial acid hydrolysis and methylation studies suggested that the heteroglycan consisted of main units of 1→6 linked glucopyranosyl residues possessing branch points at position 3 in part and small amounts of 1→3 linked glucopyranosyl residues, to which minor units of mannopyranosyl residues having branches at position 2 and 3, and galactofuranosyl (or galactopyranosyl) residues possessing branches at position 2 and 6 (or 3 and 6) attached. Also, the structure was proved to contain moieties of 1→4 linked glucopyranosyl, 1→2 and 1→6 linked galactfuranosyl, and non-reducing terminal glucopyranosyl and xylopyranosyl residues.View full abstractDownload PDF (827K) -
KIYOSHI TATSUMI, SHIGEYUKI KITAMURA, HIDETOSHI YOSHIMURA, YUICHI KAWAZ ...1978 Volume 26 Issue 6 Pages 1713-1717
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reduction of aromatic nitro compounds was investigated in purified milk xanthine oxidase-xanthine system. The p-substituted nitro compounds with electron-withdrawing groups served as an efficient acceptor of electron, whereas those with electron-repelling groups were less active. The reduction products formed from some nitro compounds were also examined by thin-layer chromatography and spectrophotometry. As a result, the corresponding hydroxylamines were identified in all cases. Furthermore, the reduction of ortho, meta and para isomers of some nitro compounds was investigated in the same manner. The reduction rate was greatest at para substitution of electron-withdrawing group and at meta substitution of electron-repelling group, respectively.View full abstractDownload PDF (683K) -
GIICHI GOTO, KOUICHI YOSHIOKA, KENTARO HIRAGA, MICHIO MASUOKA, RYO NAK ...1978 Volume 26 Issue 6 Pages 1718-1728
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to examine the antiandrogenic activity, a series of 16β-substituted-17β-hydroxysteroids (9 and 16) were synthesized by stereoselective introduction of β-substituents at position 16 of steroids. The corresponding 6-chloro-16β-substituted-17β-hydroxysteroids (20 and 28) and 1, 2α-methylene derivative (36) were also prepared. Among these new steroids synthesized, 17β-hydroxy-16β-ethylestr-4-en-3-one (9b : TSAA-291) was found to have the most potent antiandrogenic activity with very weak side effects and also found to be useful for a treatment of the benign prostatic hypertrophy.View full abstractDownload PDF (1147K) -
SHIGEO UKAI, CHIHIRO HARA, TADASHI KIHO, KAZUO HIROSE1978 Volume 26 Issue 6 Pages 1729-1736
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo kinds of arabinans AL-I and AL-II, as neutral homoglycan, have been isolated by alkaline extraction from azuki beans, which are the seeds of Phaseolus radiatus L. var. aurea PRAIN. Both arabinans were homogeneous as judged by gel filtration (Sephadex G-200), and electrophoresis. Structural analysis indicated that these arabinans had a chain of 1→5 linked L-arabinofuranose units bearing a highly branched structure with branching points either at each of position 2 and 3 or at both these positions, to which non-reducing terminal furanosyl residues were attached. At the branching points, the proportion of 1→2 linkage was larger than that of 1→3 linkage. Both arabinans were similar, but some significant differences between AL-I and AL-II were observed in physical properties such as molecular weight and solubility in 80% aqueous ethanol solution. The structural differences between two were found in such respects that the amount of non-reducing terminal residues in AL-I was slightly larger than that in AL-II, and the proportion of 1→5 linkage bearing branch point at position 2 or 3 in AL-I was lower than that in AL-II.View full abstractDownload PDF (975K) -
TOSHIO SHIBAZAKI, TOKIKO NISHIMURA, MACHIKO HARA, TADASHI IIJIMA1978 Volume 26 Issue 6 Pages 1737-1745
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe fluorescence reaction of salicylic acid and its derivatives with boric acid was successfully applied to their micro-analyses. The recommened procedures were as follows : Seven milliliters of the glacial acetic acid solution of a sample of salicylid acids (5×10-6-5×10-8M) was mixed with 1.0 ml of sulfuric acid-glacial acetic acid solution with concentration represented in Table II, 1.0 ml of acetic anhydride, and 1.0 ml of boric acid-glacial acetic acid solution, stoppered and allowed to keep at 60° for 10 min. Then the fluorescence intensity of the solution was measured at the excitation and fluorescence maxima of each of the samples shown in Table II. In the case of 4-hydroxysalicylic acid and 5-aminosalicylic acid, 8.0 ml of each solution was mixed with 1.0 ml of 5% boric acid-acetic anhydried solution, and the mixture was kept at 60° for 10 min. Then 1.0 ml of 0.01 N sulfuric acid solution in-glacial acetic acid was added to the mixture. The coefficients of variation for these four compounds (1×10-6M) were 0.8-1.0%. Among diverse compounds, quinie ethylcarbonate disturbed the determination. This fluorometry was applied to the determination of salicylid acid in fermented liquor, blood plasma and urine, and the analytical results agreed well with those obtained by the colorimetric method.View full abstractDownload PDF (896K) -
TOSHIYUKI CHIKUMA, KAZUO NEGISHI, HIKOYA HAYATSU1978 Volume 26 Issue 6 Pages 1746-1752
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDehalogenations of 5-bromo- and 5-iodo-2'-deoxyuridine by thiol compounds in aqueous solutions were studied. The thiols used were cysteine, cysteine methyl- and ethyl-esters, cysteamine, homocysteine, glutathione, 2-mercaptoethanol, and 2-mercaptopropionic acid. The products of these reactions and the rate constants were determined. At pH 8 and 37°, the dehalogenation rates by these thiols decreased in above-mentioned order. 5-Alkylthiouracil derivatives were found in products of the reactions between 5-bromo-2'-deoxyuridine and cysteine, cysteine ethyl ester, cysteamine, homocysteine and glutathione, as well as of the reaction between 5-iodo-2'-deoxyuridine and cysteine. This indicated that the SN2 mechanism proposed in a previous paper (Y. Wataya, K. Negishi and H. Hayatsu, Biochemistry, 12, 3992 (1973)) is generally operating in the dehalogenations of these compounds with thiols.View full abstractDownload PDF (781K) -
KAZUHIDE KAMIYA, YOSHIKAZU WADA, KOICHI KONDO1978 Volume 26 Issue 6 Pages 1753-1760
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe complete three dimensional structure of 9-propionylmaridomycin III (PMDM III) has been determined by the X-ray analysis of its iodo adduct. This is the first case that the structure of the intact 16-membered ring marcrolide has been determined by the X-ray analysis. Hydrophilic substituent groups of the 16-membered macrocyclic ring of PMDM III lie on one side of the ring, while the hydrophobic substituents are directed to the other side of the ring. This characteristic arrangement of the substituents gives the macrocyclic ring of PMDM III two physicochemically different faces, which have previously been pointed out in the case of the 14-membered ring of erythromycin A. Similar spatial arrangement of substituents on the macro ring is also found in the conformation of demycarosyl isoleucomycin A3 elucidated by X-ray analysis of its hydrobromide. The spatial interrelation of 6-formylmethyl, 2'-hydroxyl and 3'-dimethylamino groups, which have been known most important substituents for the biological activities of the 16-membered ring macrolide antibiotics, is strikingly similar between PMDM III and demycarosyl isoleucomycin A3.View full abstractDownload PDF (767K) -
TAKEO KOBAYASHI, YUJI IWANO, KOICHI HIRAI1978 Volume 26 Issue 6 Pages 1761-1767
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe chloro-β-lactam derivatives (VII and XIIIa, b, c) were prepared from the readily available 4-acetoxy-2-azetidinone (III) in four steps. Silver triflate treatment of these chloro β-lactam derivatives in the presence of NaH gave the oxapenam derivatives (VIII and XIVa, b, c) in 3.5-11.6% yield after careful chromatography separation. Preliminary biological activities of natural and synthesized oxapenam derivatives are listed.View full abstractDownload PDF (876K) -
JUNZO HIROSE, YOSHINORI KIDANI1978 Volume 26 Issue 6 Pages 1768-1775
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe mechanism and rate of cobalt removal reaction from cobalt-enzyme with various chelating agents were investigated, in comparing with that of zinc-enzyme. The mechanism of cobalt removal reaction was the same as that of zinc-enzyme and the selectivity of chelating agents against zinc-enzyme and cobalt-enzyme was almost the same. The second-order rate constant of cobalt removal from cobalt-enzyme with various chelating agents (kapp) was much larger (13-30 times) than that of zinc-enzyme. The thermodynamic parameter of metal removal reaction was measured by the reaction of 5-methyl-1, 10-phenanthroline with cobalt- and zinc-enzyme. Activation enthalpy for breakdown of the ternary complex of cobalt- and zinc-enzyme was almost the same (28-29 kcal mol-1) but activation entropy (33 cal deg-1 mol-1) for breakdown of the ternary complex of cobalt-enzyme was much larger than that (22 cal deg-1 mol-1) of zinc-enzyme. This is the reason why kapp of the cobalt-enzyme is much larger than that of zinc enzyme.View full abstractDownload PDF (878K) -
TETSUYA AONO, SHOJI KISHIMOTO, YOSHIAKI ARAKI, SHUNSAKU NOGUCHI1978 Volume 26 Issue 6 Pages 1776-1785
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAntiinflammatory 4-aroyl-1-indancarboxylic acids (I) were synthesized from the corresponding 4-aroyl-1-indanones (XI) by the one-carbon homologation reaction using p-toluenesulfonylmethylisocyanide (TosMIC, II) via 4-aroyl-1-indancarbonitriles (XIV). Among them, three compounds (Ia, b and c) were resolved into their enantiomers and it was found that the antiinflammatory activity virtually resides in the levo isomers, the absolute configurations of which were assigned the sinister series by the optical rotatory dispersion spectra.View full abstractDownload PDF (1064K) -
TERUO HAYASHI, TEIKI IWAOKA, NORIKO TAKEDA, EIJI OHKI1978 Volume 26 Issue 6 Pages 1786-1797
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS3-Dithiocarbonates (1d, 1e, 3a) and 3, 4-bis analog (1b) derived from methyl 2, 6-dibenzyloxycarbonylamino-2, 6-dideoxy-α-D-glucopyranoside (1a) were converted into 3-deoxy compounds (1c, 1f, 3b) and 3-eno compound (2) respectively in good yield on treatment with tributylstannane. This reaction process was extended into the field of aminoglycoside antibiotics, giving 5-deoxykanamycin B (8a), 3', 4', 5-trideoxykanamycin B (8c), 3', 4', 5-trideoxy-3'-enokanamycin B (8b), 6-deoxybutirosin A (9a), and 3'-deoxybutirosin A (9b) whose antibacterial activities were discussed. Structures of these deoxysugars were confirmed by carbon-13 nuclear magnetic resonance spectrometry.View full abstractDownload PDF (1250K) -
AKIRA YAGI, NOBUYUKI OKAMURA, YASUSHI HARAGUCHI, KANJI NODA, ITSUO NIS ...1978 Volume 26 Issue 6 Pages 1798-1802
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new p-coumaroylates of alphitolic acid were isolated from the fruits of Zizyphus jujuba (Rhamnaceae) and were characterized to be 3-O-trans-p-coumaroyl-, 2-O-trans-p-coumaroyl- and 3-O-cis-p-coumaroyl alphitolic acid on the basis of chemical and spectral evidence.View full abstractDownload PDF (704K) -
TOSHIHIKO HASHIMOTO, YOICHI KAWANO, SACHIKO NATSUME, TERUO TANAKA, TAI ...1978 Volume 26 Issue 6 Pages 1803-1811
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS7-Acylamido-3-[2-(1-methyl-1H-tetrazol-5-yl) vinyl]-3-cephem-4-carboxylic acids including the 7-methoxy derivatives were prepared by two synthetic methods. The first method involves the reaction of the 3-bromomethylcephalosporin derivative (III) with 5-methylsulfinylemthyl-1-methyl-1H-tetrazole (IV) followed by thermal elimination leading to an olefinic compound (VI). An alternative olefin formation was carried out by utilizing the Wittig reaction of the 3-formylcephalosporin derivative (X). Among the 3-tetrazolylvinylcephalosporin derivatives, the mandelamido derivative (XVa) showed the best in vitro antibacterial activities against gram negative bacteria.View full abstractDownload PDF (1020K) -
ISAO IKEUCHI, TAMEYUKI AMANO1978 Volume 26 Issue 6 Pages 1812-1817
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn abnormally greenish tint appeared in the blood plasma of adult rhesus monkeys that had been daily administered an intramuscular injection of 1-methyl-2-(β-naphtyl)-aziridine or chlorpromazine. This greenish component in the monkey plasma could not be extracted with cyclohexane, 1, 2-dichloroethane or n-butyl alcohol, and the greenish tint was scarcely changed by the addition of ethylenediaminetetraacetate. The greenish monkey plasma showed a visible absorption band at 610 nm like the blue fraction separated from it. These absorption bands at 610 nm, both in the greenish monkey plasma and the separated blue fraction, disappeared with the addition of ascorbic acid and reappeared with oxygen, as with human ceruloplasmin (Cp). The electron spin resonance spectrum of the greenish monkey plasma was similar to that of human Cp. Furthermore, the major portion of copper in monkey plasma was in the blue fraction, and the total plasma copper and p-phenylenediamine oxidase activity (PPD activity) increased with deepening of the green tint. These results suggested that the abnormal greenish tint of the monkey plasma is due to the presence of the blue copper protein Cp in the plasma. Based on examination of the relationships between total plasma copper and PPD activity in monkey and rat plasma, monkey Cp activity was compared with those of other mammalian species.View full abstractDownload PDF (639K) -
TAKUMI KOJIMA, MITSURU HASHIDA, SHOZO MURANISHI, HITOSHI SEZAKI1978 Volume 26 Issue 6 Pages 1818-1824
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA timed-release derivative of mitomycin C (MMC), agarose bead conjugate (MMC-AB), was synthesized using cyanogen bromide method. MMC was released successively for considerably longer period from MMC-AB in vitro and in vivo after intraperitoneal injection to mice. MMC-AB exhibited almost identical inhibitory effect against growth of Ehrlich ascites carcinoma (EAC) cells to free MMC and less toxicity to ddY mouse than free MMC. Calculated therapeutic index (LD10/ED90) of MMC-AB was two times greater than that of free MMC, suggesting its advantage in cancer chemotherapy. On the life span of EAC bearing ddY mouse, MMC-AB showed almost similar efficiency with that of free MMC but less activity was exhibited against BDF1 mouse transplanted L1210 leukemia.View full abstractDownload PDF (767K) -
YUTAKA YAMAMOTO, YUTAKA AZUMA, KYOKO MIYAKAWA1978 Volume 26 Issue 6 Pages 1825-1831
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of 6-methyl-2-phenyl-4H-1, 3-oxazin-4-one (1) with hydrazine hydrate, methylhydrazine and phenylhydrazine was found to yield the corresponding 1, 2, 4-triazoles 3a, 2b and 3c in 91, 52 and 76.5% yield, respectively. Whereas, 1 was treated with the respective sulfates of hydrazine, methylhydrazine and phenylhydrazine to be transformed into the corresponding pyrazoles 9a, 9b and 9c in 73.4, 61 and 42% yield, respectively. Analogously, the reaction of 14a, b with phenylhydrazine yielded the corresponding 1, 2, 4-triazole 15a, b.View full abstractDownload PDF (869K) -
AKIRA UENO, KUNIO MORINAGA, SEIGO FUKUSHIMA, SHIGENOBU OKUDA1978 Volume 26 Issue 6 Pages 1832-1836
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe alkaloids of the epigeal part of Japanese Sophora flavescens AITON were investigated for the first time, and (-)-Δ7-dehydrosophoramine (XII), the most highly unsaturated compound among the known lupin alkaloids of matrine type, was isolated and the structure was determined, and (+)-sophocarpine-N-oxide (XI) was isolated from this plant at first time.View full abstractDownload PDF (626K) -
MAKOTO UCHINO, KUNIO SUZUKI, MINORU SEKIYA1978 Volume 26 Issue 6 Pages 1837-1845
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSConvenient syntheses of sodium alkane- and arenesulfinates in high yields and purities have been provided by nucleophilic substitution reactions of alkyl phthalimidomethyl sulfones and aryl succinimidomethyl sulfones, respectively, with ethoxide or thiolates.View full abstractDownload PDF (826K) -
HIDEHARU YOKOI, SABURO ENOMOTO1978 Volume 26 Issue 6 Pages 1846-1851
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSComposition and degree of polymerization of polysilicic acids in magnesium silicates were studied by the trimethylsilylation method. The trimethylsilylated derivatives of silicic acids obtained by acid hydrolysis of the silicates were separated into soluble and insoluble fractions. Orthosilicic acid and a few species of polysilicic acids were determined by gas-liquid chromatography in the soluble fraction. The results are as follows : monosilicic acids (0.16-0.96%), disilicic acids (0.02-0.31%), trisilicic acids (-0.06%), cyclic tetrasilicic acids (-0.11%), the other soluble polysilicic acids (0.35-1.45%), and insoluble polysilicic acids (75.78-82.07%). These results apparently suggest that, when magnesium silicate is hydrolyzed in gastric juice, most of silicic acids produced may lead to insoluble silica gel and the other, such as orthosilicic acid and several polysilicic acids with low degree of polymerization, may disperse in gastric juice. Possible absorption of silicic acids from digestive tracts following oral administration of the antacid was discussed.View full abstractDownload PDF (952K) -
ISAO KITAGAWA, MOTOMASA KOBAYASHI, TAMIO SUGAWARA1978 Volume 26 Issue 6 Pages 1852-1863
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe saponin mixture has been isolated from the whole body of starfish Acanthaster planci L. (crown of thorns). By use of the glycosidase mixture from the large marine gastropod Charonia lampas, which is known as a natural enemy of A. planci, two genuine sapogenols named thornasterol A (8) (major) and thornasterol B (9) (minor) have been isolated as their diacetates from the saponin mixture. On the basis of chemical reactions and physicochemical evidence, the structures of diacetyl-thornasterol A and diacetyl-thornasterol B have been elucidated to be 3β, 6α-diacetoxy-5α-cholest-9 (11)-en-20-ol-23-one (8a) and 24ε-methyl-3β, 6α-diacetoxy-5α-cholest-9 (11)-en-20-ol-23-one (9a), respectively. Furthermore, the sulfate group contained in the parent saponins of thornasterol A (8) and B (9) has been shown to attach to 3β-OH of the respective sapogenols. It has been also suggested that the pregnane-type sapogenol (1), which has been hitherto isolated not only from A. planci but also from many other species of Asteroidea, may be an artifact sapogenol.View full abstractDownload PDF (1305K) -
ISAO KITAGAWA, MOTOMASA KOBAYASHI1978 Volume 26 Issue 6 Pages 1864-1873
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe major saponin named thornasteroside A (5) has been isolated from the whole body of starfish Acanthaster planci L. (crown of thorns). In order to facilitate the structural study, thornasteroside A (5) has been converted to a pentaglycoside (designated as dsp-1), which corresponds to a desulfated pregnane-type derivative of 5. On the bases of chemical reactions and physicochemical evidence, the structure of dsp-1 has been elucidated as 10. Based on the accumulated evidence in this and the preceding papers, the structure of thornasteroside A has been established as 20-hydroxy-6α-O-{β-D-fucopyranosyl (1→2)-β-D-galactopyranosyl (1→4)-[β-D-quinovopyranosyl (1→2)]-β-D-xylopyranosyl (1→3)-β-D-quinovopyranosyl}-5α-cholest-9 (11)-en-23-on-3β-yl sodium sulfate (5).View full abstractDownload PDF (1177K) -
SHINZO KANO, TSUTOMU YOKOMMATSU, TOSHIHIRO ONO, SATOSHI HIBINO, SHIROS ...1978 Volume 26 Issue 6 Pages 1874-1879
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe Knoevenagel condensation of methylthioacetonitrile with carbonyl compounds such as benzaldehyde, cyclopentanone, phenylacetone, was examined to give the corresponding α-methylthio unsaturated nitriles. Desulfurization of β-aryl-α-methylthioacrylonitriles (5a-f) with Raney Nickel afforded cis-β-arylacrylonitriles (6a-f). Reduction of 5a-c with sodium borohydride gave α-methylthiophenylpropionitriles (7a-c), which were converted to trans-cinnamonitriles (9a-c). α-Methylthio-α, β-unsaturated nitriles (11a-d) were lead to α-ethyl-α-methylthio-β, γ-unsaturated nitriles (12a-d). Furthermore, the α-methylthiophenylpropionitrile (7b) was converted to 4-methoxybenzyl methyl ketone.View full abstractDownload PDF (623K) -
NARAO TAKAO, KINUKO IWASA, MIYOKO KAMIGAUCHI, MAKIKO SUGIURA1978 Volume 26 Issue 6 Pages 1880-1889
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn some hydrobenzo [c] phenanthridine-type alkaloids, the preferred conformation of the B and C rings in solution and the orientation of the N-methyl group in solution and in crystalline state were examined using infrared, proton magnetic resonance, and carbon magnetic resonance spectroscopies. The alkaloids, chelidonine (1), corynoline (2), 6-quasi-axial and quasi-equatorial alkyl-substituted derivatives of 2 (2a'-c' and 2a-c), and corynolamine (3), exist in the conformation with type I-cis and B/C-half chair/half chair, 6-quasi-axial alkyl-substituted derivatives of 2-acetate (2b'-Ac and 2a'-Ac) and 3-diacetate adopt the conformation with type I-cis and B/C-twist half-chair/half chair, and 2-acetate and its 6-quasi-equatorial alkylsubstituted derivatives (2a-Ac and 2b-Ac) possess the conformation with type I-cis and B/C-half chair/twist halfboat. Chelidonine acetate (1-Ac) exists in the conformation with type II-cis and B/C-half chair/twist half-chair. (+)-14-Epicorynoline (4) and its acetate adopt the conformation with trans and B/C-half chair-twist half-chair. The preferred conformation of the N-methyl group in solution in 1, 2, 2a-c, 2a'-c', 2a-Ac, 2b-Ac, and 3 is equatorial and that in 1-acetate, 2a'-Ac, 2b'-Ac, 3-diacetate, 4, and 4-acetate is axial. In 2-acetate, the position of equilibrium in the N-Me(ax)⇄N-Me-(eq) shifts to the equatorial side than the axial side. Orientation of the N-methyl group in a crystalline state is in accord with the preferred conformation in solution.View full abstractDownload PDF (967K) -
TAKASHI TSUCHIYA, JYOJI KURITA1978 Volume 26 Issue 6 Pages 1890-1895
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe previously unknown 3H-1, 2- (5), 3-acetoxy-3H-1, 2- (6), and 3-methoxy-3H-1, 2-(7) benzodiazepines were prepared from the 1H-1, 2-benzodiazepines (1) in high yields and the energy barriers to ring inversion for the 3H-diazepines (5) were estimated from nuclear magnetic resonance spectral data. Treatment of 5 with both bases and acids resulted in the tautomerization to give the 1H-isomers (1). However, the 3H-diazepines (5) gave 3-vinylindazoles (8 or 9) by thermolysis and gave the indazoles (8 or 9) and indenes (10) by photolysis in good yields, probably via the diradical (11) or the tetracyclic intermediates (12).View full abstractDownload PDF (628K) -
TAKASHI TSUCHIYA, JYOJI KURITA1978 Volume 26 Issue 6 Pages 1896-1900
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of the 3H-1, 2-benzodiazepine 2-oxides (8), prepared from the 3H-1, 2-benzodiazepines (7) and m-chloroperbenzoic acid, with both acids and bases such as hydrogen chloride, acetic acid, sodium alkoxides, carbanions, and sodium cyanide afforded the corresponding previously unknown 3-substituted 1, 2-benzodiazepines (10-17) in moderate yields.View full abstractDownload PDF (646K) -
MAKIKO SUGIURA, NARAO TAKAO, KINUKO IWASA, YOSHIO SASAKI1978 Volume 26 Issue 6 Pages 1901-1907
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe equilibriums"trans⇄cis"a""of some benzo [a] quinolizidine derivatives were investigated by three different approaches ; 13C chemical shift of C-6 and 13C paramagnetic shift induced by Ni (AA)2 as well as Bohlmann bands of infrared spectra. By means of these approaches, the equilibrium states of these derivatives were determined, and the displacement of C-6 chemical shift was approved as a guide to estimate the state of the equilibrium and to indicate the relative weight of each conformer.View full abstractDownload PDF (736K) -
KAZUO ITO, JENGSHIOW LAI1978 Volume 26 Issue 6 Pages 1908-1911
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe substance M described in our previous paper was found to be a mixture of two similar triterpenoid compounds, which were named marsformoxide A and B. As the result of spectroscopic and chemical investigation, it has been demonstrated that the stereostructures of marsformoxide A and B were represented, respectively, by the formulas I and II.View full abstractDownload PDF (565K) -
YOSHINORI KIDANI, KENJI INAGAKI1978 Volume 26 Issue 6 Pages 1912-1914
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1-(Methylthio) phenazine (mtph) reacts with platinum (II) and palladium (II) in acetone-water to give orange complexes. The mtph coordinates to metal through the sulfur and nitrogen atoms as a bidentate ligand, and the two halogen atoms of the complexes are in cis-configuration. When the orange complex, PtCl2 (mtph), was refluxed in N, N-dimethylformamide, a reddish violet S-demethylated complex was produced. On the other hand, PdCl2 (mtph) did not give any demethylated complexes under similar conditions.View full abstractDownload PDF (418K) -
MASAYOSHI YAMAGUCHI, TAKEO YAMAMOTO1978 Volume 26 Issue 6 Pages 1915-1918
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA calcium binding substance has been isolated from the soluble fraction of normal rat liver. The calcium binding substance was purified by means of gel filtration on Sephadex G-75 and G-50 followed by ion-exchange chromatography on diethylaminoethyl-cellulose. By these methods, the calcium binding activity from the soluble fraction has been purified several 100-fold and the homogeneity of the calcium binding substance has been established by polyacrylamide gel electrophoresis.View full abstractDownload PDF (616K) -
TETSUJI KAMETANI, YOSHIO KIGAWA, KIMIO TAKAHASHI, HIDEO NEMOTO, KEIICH ...1978 Volume 26 Issue 6 Pages 1918-1922
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of 2, 3-dihydro-7-methoxy-6-methyl-1H-pyrrolo [1, 2-a] indole-9-carboxaldehydes (2), (3), (4), (5), and (6) with thiolacetic acid in the presence of 6 N sulphuric acid at room temperature gave 9-diacetylthiomethyl-2, 3-dihydro-7-methoxy-6-methyl-1H-pyrrolo [1, 2-a] indoles (12), (13), (14), (15), and (16), respectively. The same reaction of the compound (2) at 0° afforded 1-acetoxy-9-diacetylthiomethyl-2, 3-dihydro-7-methoxy-6-methyl-8-nitro-1H-pyrrolo [1, 2-a] indole (11). Successive treatment of the compound (11) with absolute methanol in the presence of sodium methoxide gave 2, 3-dihydro-1-hydroxy-7-methoxy-9-dimethoxymethyl-6-methyl-8-nitro-1H-pyrrolo [1, 2-a] indole (17).View full abstractDownload PDF (637K) -
TETSUJI KAMETANI, TATSUSHI OHSAWA, MASATAKA IHARA, KEIICHIRO FUKUMOTO1978 Volume 26 Issue 6 Pages 1922-1926
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of the sulfinamide anhydride (2), prepared from anthranilic acid (1), with 3, 4-dihydro-6, 7-dimethoxyisocarbostyril (9) gave 5, 6, 7, 8-tetrahydro-2, 3-dimethoxy-8-oxoisoquinolo [1, 2-b] quinazoline (10), which was also obtained by heating isatoic anhydride (3) with 9. Similarly, rutecarpine (6) was synthesised by the reactions of 1, 2, 3, 4-tetrahydro-1-keto-β-carboline (13) with the sulfinamide anhydride (2) or isatoic anhydride (3). Heating 3, 4-dihydro-β-carboline (5) with 3 also afforded rutecarpine (6). Furthermore the phosphates (8a) and (12) were isolated on treatment of the urethanes (7a) and (11) with phosphoryl chloride.View full abstractDownload PDF (700K) -
HAJIME GOTO, MASAMI MORI, SETSUZO TEJIMA1978 Volume 26 Issue 6 Pages 1926-1929
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEffects of solvents and catalysts in catalytic hydrogenation of the exocyclic double bond in disaccharide-5-ene heptaacetates, synthesized from maltose, lactose, and cellobiose, were investigated. A stereospecific hydrogenation proceeded in such a way that the corresponding 6-deoxy-L-ido isomer was predominant over the 6-deoxy-D-gluco isomer. Preparations of 6-deoxy-maltose, 6-deoxy-α-cellobiose, 4-O-α-D-glucopyranosyl-6-deoxy-L-idopyranose, and 4-O-β-D-glucopyranosyl-6-deoxy-L-idopyranose were also described.View full abstractDownload PDF (571K) -
TOZO FUJII, TAISUKE ITAYA, TOHRU SAITO, MITSURU KAWANISHI1978 Volume 26 Issue 6 Pages 1929-1936
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeveral 1-substituted 5-aminoimidazole-4-carboxamidines (5g-j) have been prepared from the corresponding N'-alkoxyamidines (4a-f) by catalytic hydrogenolysis. In the hydrogenolysis of 4a-f using Raney Ni catalyst, addition of one molar equivalent of hydrochloric acid accelerated the reaction to give 5g-j in acceptable yields. The structures of 5g-j have been confirmed by cyclization to 9-substituted adenines (6g-j) and by alkaline hydrolysis to 1-substituted derivatives (7g-j) of 5-aminoimidazole-4-carboxamide (AICA).View full abstractDownload PDF (1026K) -
SHIN MATSUURA, MUNEKAZU IINUMA1978 Volume 26 Issue 6 Pages 1936-1941
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSStructure of substances XIV and XVIII, obtained previously among the constituents of the calyx of persimmons (Diopyros kaki, Ebenaceae), was examined, and XIV was determined as astragalin (kaempferol 3-β-D-glucopyranoside) and XVIII as n-butyl-β-D-fructopyranoside, although the latter was considered to be an artifact. Carbon-13 NMR spectra of kaempferol, quercetin, trifolin, astragalin, and hyperin were measured and their structure was proved from the assignment of NMR signals.View full abstractDownload PDF (673K) -
ISAMU MURAKOSHI, FUMIO IKEGAMI, KAORU HARADA, JOJU HAGINIWA1978 Volume 26 Issue 6 Pages 1942-1945
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA cell free system from leguminous plants has been shown to catalyze the formation of O-ureidoserine (4) from O-acetyl-L-serine (2) and N-hydroxyurea (3). Other possible products, β-(1-hydroxyureido) alanine (5) and β-(3-hydroxyureido) alanine (6), were not formed under the same conditions.View full abstractDownload PDF (593K) -
TAKAFUMI WATANABE, TETSUYA SUGA1978 Volume 26 Issue 6 Pages 1945-1946
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new method of colorimetric determination of uric acid, using uricase and catalase is reported. This method is based on the combination of enzyme reactions and colorimetric procedure with using 4-amino-3-hydrazino-1, 2, 4-triazole, a highly sensitive reagent for formaldehyde. The color developed in a straight line passing through the original point at least within the absorbance unit of 1.5 at 550 nm, corresponding to 16 mg/dl of the uric acid concentration of the sample.View full abstractDownload PDF (343K) -
KENTARO HIRAI, TERUYUKI ISHIBA, HIROHIKO SUGIMOTO, KAZUYUKI SASAKURA, ...1978 Volume 26 Issue 6 Pages 1947-1950
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA number of peptido-aminobenzophenones were prepared as ring-opened derivatives of 1, 4-benzodiazepines. These compounds were prepared from 2-aminobenzophenones, 2-aminobenzhydrols, or indoles and appropriate protedcted dipeptides or protected amino acids by coupling, oxidation (if necessary), and deprotection. Some title compounds had very high activities in antipentylenetetrazole and fighting tests in mice when orally administered. Very weak toxicity was also found in these compounds. Water solubility of peptido-aminobenzophenone salts and pH of their aqueous solution were also tested.View full abstractDownload PDF (474K) -
YOSHIYASU KITAHARA, HARUHIRO OKUDA, KOICHI SHUDO, TOSHIHIKO OKAMOTO, M ...1978 Volume 26 Issue 6 Pages 1950-1953
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAza-arene oxides, dibenz [a, j] acridine-5, 6-oxide, dibenz [a, h] acridine-12, 13-oxide, dibenz [c, h] acridine-5, 6-oxide, and 10-azabenzo [a] pyrene-4, 5-oxide were synthesized and their mutagenic activity to Salmonella typhimurium strains TA 98 and TA 100 was tested.View full abstractDownload PDF (481K) -
MASAICHIRO MASUI, CHIHIRO UEDA, HIDENOBU OHMORI1978 Volume 26 Issue 6 Pages 1953-1954
Published: June 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAnodic oxidation of N-alkylcarboxanilides in methanol at controlled potentials resulted in the formation of N-alkylbenzoxazolium perchlorate via nucleophilic attack of the carbonyl oxygen to the phenyl ring.View full abstractDownload PDF (358K)
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