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Volume 24, Issue 8
Displaying 1-50 of 53 articles from this issue
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YOSHITAKA TAKEHISA, YUICHI KAWAZOE, TANEZO TAGUCHI1976 Volume 24 Issue 8 Pages 1691-1697
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of anti-oxime (1) of 2-phenoxycyclohexanone was attempted in continuation of the former studies on the Grignard reactions of oximes. Consequently, it ended in a result entirely different from the Hoch-Campbell reaction and also the intramolecular ringclosure reaction which has been previously reported. causing the elimination of phenol and the productions of aniline and 2-phenoxycyclohexanone in main. The reaction pathway was discussed. Additionally, the government of reaction by both changes of 2-substituent on cyclohexanone oxime and Grignard reagent was preliminarily examined.View full abstractDownload PDF (862K) -
MAMORU SUGIURA, KAZUYUKI HIRANO, SHIRO IINO, HIROSHI SUZUKI, TOSHITSUG ...1976 Volume 24 Issue 8 Pages 1698-1703
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAlkaline phosphatase (E. C. 3. 1. 3. 1) from human kidney was purified by n-butanol extraction, ammonium sulfate fractionation, and chromatography over DEAE-cellulose, CM-cellulose, and Sephadex G-200. The purified enzyme exhibited a single protein band by disc electrophoresis. This enzyme was activated by MgCl2 and NiCl2, but inhibited by CdCl2, and had an optimum pH at 11.4. Other properties of kidney alkaline phosphatase were also investigated and discussed.View full abstractDownload PDF (621K) -
YOSHIRO KOBAYASHI, ITSUMARO KUMADAKI, HIROSHI HAMANA1976 Volume 24 Issue 8 Pages 1704-1707
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAlkylation of 1-position of 5-methyl-1, 2, 3, 4-tetrahydro-1, 6-naphthyridine (I) does not proceed in ordinary methods. I shows quite peculiar behavior in ultraviolet spectrum ; absorption maximum shows bathochromic shift on protonation. Based on these data alkylation was successfully carried out in the presence of sodium amide.View full abstractDownload PDF (445K) -
MITSURU FURUKAWA, TCHIAKI SUDA, SEIGORO HAYASHI1976 Volume 24 Issue 8 Pages 1708-1713
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNew compounds of N-(substituted thio) isatins (III) were synthesized and reactions with several nucleophiles were examined in comparison with the reaction using N-(substituted thio) phthalimides (I) and N-(substituted thio) succinimides (II) : All of I, II, and III reacted with organometallic compounds, cyanide ion, and trichloromethyl carbanion to give sulfides (IV), thiocyanates (V), and trichloromethyl sulfides (VI) respectively. Different from I and II, however, the reaction of III with amines afforded 3-amino-1-substituted thio-3-hydroxy-2-oxo-indoles (X), with no formation of any sulfenamides anticipated.View full abstractDownload PDF (688K) -
SEIICHIRO YOSHIDA, YOSHIAKI KAMANO, TAKESHI SAKAI1976 Volume 24 Issue 8 Pages 1714-1717
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe surface anesthetic activities of ten bufadienolides, i. e., resibufogenin, bufalin, bufotalin, desacetyl-bufotalin, cinobufagin, desacetyl-cinobufagin, cinobufotalin, desacetyl-cinobufotalin, telocinobufagin and marinobufagin, were studied using the guinea pig cornea. With exceptions of resibufogenin and marinobufagin, all substances tested were more effective than cocaine. Their anesthetic activities were in the following order : bufalin > telocinobufagin > bufotalin > cinobufagin > cinobufotalin > desacetyl-bufotalin ≨ desacetyl-cinobufagin ≨ desacetyl-cinobufotalin. Resibufogenin and marinobufagin had no appreciable effect on the cornea. There is some correlation between the chemical structure and the surface anesthetic activity in the bufadienolides tested.View full abstractDownload PDF (480K) -
TOSHIO MIYAZAKI, YASUTA NAOI1976 Volume 24 Issue 8 Pages 1718-1723
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMajor water-soluble polysaccharide obtained from the cell wall of Cladosporium trichoides by diethylaminoethyl-cellulose column fractionation is a heteroglycan, [α]20D+50°(c=1, H2O), which is composed of D-galactose, D-glucose, D-mannose, and small amount of L-rhamnose (1.4 : 1.4 : 1.0 : 1.0). The results of periodate oxidation, Smith-type degradation, methylation, and gas-liquid chromatography-mass spectrometry spectra show that the polysaccharide has branched structure and contains 1, 2-, and 1, 2, 6-linked galacto-furanosyl, 1, 3, 6-linked mannopyranosyl, and a small amount of 1, 4-linked glucopyranosyl residues as the main units. The terminal residues are glucopyranosyl and mannopyranosyl residues.View full abstractDownload PDF (791K) -
SANJI HAGISHITA, KAORU KURIYAMA1976 Volume 24 Issue 8 Pages 1724-1730
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSthreo-1-Hydroxy-2-(isopropylamino)-[10]-paracyclophane (1) was prepared and resolved into one enantiomer. The absolute configuration of 1 was deduced from the analysis of circular dichroism (CD) spectra using Snatzke's sector rule and induced CD of Cu(su)2(ip)2 and Pr(DPM)3. Intrinsic sympathomimetic activity of 1 and threo-and erythro-1-(4-tolyl)-2-isopropylamino-1-propanol were tested on the isolated guinea pig heart.View full abstractDownload PDF (765K) -
MITSUO AKIBA, YOSHIYUKI KOSUGI, TOYOZO TAKADA1976 Volume 24 Issue 8 Pages 1731-1736
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIndazoloquinone (4) or 5-substituted indazoloquinones (5a-c) were obtained with an acid-catalyzed substitution reaction of mono-(2a-c) or diaminoquinone tosylhydrazones (3a-c) in high yields. The reaction mechanism and rate were investigated.View full abstractDownload PDF (699K) -
NORIKO MOTOHASHI, ITSUHIKO MORI, YUKIO SUGIURA1976 Volume 24 Issue 8 Pages 1737-1741
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS^13C-Nuclear magnetic resonance (CMR) and Raman spectra of ergothioneine and its mercury complex have been recorded as function of pH. The 13C-signals of ergothioneine is assigned by comparison with the chemical shifts of histidine, 2-mercaptoimidazole and betaine. Ergothioneine is present in thione form in an aqueous solution or a solid state. In basic solution, ergothioneine exists as thiolate ion upon the deprotonation of the imidazole ring, and the tautomeric form of its imidazole ring is predominantly the 1-H tautomer. The result of 13C-NMR and raman spectra support that ergothioneine coordinates to Hg (II) ion through the thiolate sulfur.View full abstractDownload PDF (615K) -
KAZUYUKI KIZUKI, CHIAKI MORIWAKI, YOSHIO HOJIMA, HIROSHI MORIYA1976 Volume 24 Issue 8 Pages 1742-1748
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPotent kininase activities were found in Japanese mushrooms. Especially Tricholoma conglobatum (shimeji, in Japanese) contained 40-334 kininase units/g and the enzyme was purified by water extraction, ammonium sulfate fractionation, diethylaminoethyl (DEAE)-Sephadex A-50 chromatography and Sephadex G-100 gel filtration. The final preparation gave a single band in disc electrophoresis and its kininase activity, that was expressed in terms of μg bradykinin degraded in 1 min at 30°, was 480 units/E280. This value was extremely potent, so this enzyme could be expected as a useful agent on the clinical purposes or other investigations of kallikrein-kinin system. The sites of action of this enzyme on bradykinin molecule were investigated by examination of 1-dimethylaminonaphthalene-5-sulphonyl (DNS)-modified products, which were liberated from bradykinin by this enzyme, on thin layer chromatography. It cleaved Gly4-Phe5 and Pro7-Phe8 bonds and the former bond was split more easily than the latter one.View full abstractDownload PDF (872K) -
AKIRA NAKAGAWA, KAZUHIRO SUZUKI, KAZUYOSHI IWASAKI, KIYOFUMI KAJI, SAT ...1976 Volume 24 Issue 8 Pages 1749-1756
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn aglycone moiety of leucomycin-A3 (1), leuconolide-A3-5, 18-hemiacetal (3), was isolated by the application of a modified Polonovski-reaction to leucomycin-A3 N-oxide (2). Two neutral macrolides, 2'-O-acetyl-3'-N-desdimethylamino-3'-oxo-leucomycin-A3 (5) and 2'-O-acetyl-3'-N-desmethyl-N-acetyl leucomycin-A3 (8) in which the mycaminose moiety of 1 was modified, were also isolated from the same reaction. In a similar manner, an aglycone, 9-dehydro-18-dihydro-leuconolide-A3 (12) was obtained from 9-dehydro-18-dihydro-leucomycin-A3 (10). While the latter as an isomer of 1, differing with respect to the position of carbonyl group on the lactone ring, has significant antimicrobial activity neither its aglycone 12 nor the aglycone of leucomycin-A3 show antimicrobial activity.View full abstractDownload PDF (929K) -
SHINICHIRO HASHIMOTO, MICHIYO SHIZU, SHIRO TAKAHASHI1976 Volume 24 Issue 8 Pages 1757-1764
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe in vitro metabolism of generally labelled 3H-3-(1-hydroxy-2-piperidinoethyl)-5-phenylisoxazole (3H-31252-S) using the 9000xg supernatant fraction of rabbit liver homogenate was studied. The metabolites were indentified and determined quantitatively by reverse isotope dilution analysis. The results indicated that it was extensively metabolized and the main metabolic pathways were N-oxidation of piperidine and p-hydroxylation of phenyl ring. 3-{1-Hydroxy-2-(4-hydroxypiperidino) ethyl}-5-phenylisoxazole (XVII) showed slightly stronger analgesic activity than the parent compound 31252-S. All metabolites were less foxic than the parent 31252-S.View full abstractDownload PDF (986K) -
HIDEO OISHI, YOICHI USHIO, KAZUMI NARAHARA, MITSUNORI TAKEHARA1976 Volume 24 Issue 8 Pages 1765-1773
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSComparative studies of oily vehicles, hydrocarbons (HC), esters (E), and tri-glycerides (TG), were done on percutaneous absorption of salicylic acid (SA), physicochemical parameters. and trans-epidermal water loss(TEWL) in rat. The diffusion concept was supported experimentally ; vehicle viscosity was found to be an important restriction factor of drug absorption. In HC, which had low affinity to SA as estimated by solubility and partition coefficient, good correlation was obtained between drug absorption and viscotity, but this correlation could be seen only within the series. In spite of using the same series, the reverse effect was obtained in the lower molecular weight range of TG ; absorption decreased according to increase in affinity to SA, and maximum absorption appeared with the medium-chain length TG. In E, the skin-altering effect may have a rather important role in absorption, although the viscosity effect was seen. TEWL was suppressed by HC, promoted by E. and promoted slightly by TG. TEWL values correlated well with SA absorption suggesting the importance of the physiological effect of the vehicle in drug absorption.View full abstractDownload PDF (880K) -
TOSHIO NAKAGAWA, MITSUNORI TAKEHARA, HIDEO OISHI1976 Volume 24 Issue 8 Pages 1774-1778
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDrug absorption across the skin has been interpreted as the diffusional mass transfer of the drug starting from the vehicle, travelling through the skin tissue, and terminating at the blood stream. There may be some non-diffusional resistance against the drug migration at the vehicle-skin interface and the skin-blood interface. Simulation calculation using an electronic computer can be applied to this simple model of the thickness of the administrated vehicle, that of the skin, the diffusion coefficient in the vehicle, that in the skin, the partition coefficient between these two phases, and the non-diffusional resistance at the vehicle-skin and the skin-blood interface. The present paper describes the method of simulation which has been applied to the experimental results detailed in the succeeding paper.View full abstractDownload PDF (472K) -
MITSUNORI TAKEHARA, TOSHIO NAKAGAWA, YOICHI USHIO, KAZUMI NARAHARA, HI ...1976 Volume 24 Issue 8 Pages 1779-1783
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDiffusion coefficients of salicylic acid (SA) in the vehicles and the skin and partition coefficients of SA between the intact or stripped skin and a saline solution were measured, the simulation of drug absorption from the vehicles, based on the theory in Part II, was carried out, and the proportionalities between the calculated and the experimental absorption values were sufficient for all vehicles. It was found that the skin layer has an unknown nondiffusional resistance by an absorption experiment through the stripped skin. Volume effect of the drug phase on the percent absorption was interpreted by an accumulation of the vehicle at the circumference of the cell caused by an interfacial tension between the vehicle and the cell.View full abstractDownload PDF (523K) -
MASATOSHI HARADA, YUICHI FUJII, JYOJI KAMIYA1976 Volume 24 Issue 8 Pages 1784-1788
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEffects of cinnamaldehyde (CA), the main component of Chinese cinnamon which has frequently been prescribed as a remedy in Chinese medicine, on the spontaneous electroencephalograms (EEGs) as well as on the recruiting response and the augmenting response in rabbits were studied. CA converted resting patterns in the EEGs recorded from the frontal cortex, the hippocampus, the amygdala, and the midbrain reticular formation to arousal patterns in the gallamine-paralyzed preparation with the intact brain. In the midpontine pretrigeminal transected preparation, CA also induced an arousal pattern in the electrocorticogram (ECoG). In the low cerveau isole preparation, CA either converted a resting pattern in the ECoG to a sequence of low voltage fast waves or did not elicit such an action depending upon each individual preparation. In the high cerveau isole preparation, CA was not capable of producing any effect on the ECoG. CA, in higher doses, inhibited the recruiting response and the augmenting response. It was concluded that CA produced a centrally originating EEG activation through a direct or indirect excitatory action on the brainstem reticular formation.View full abstractDownload PDF (694K) -
NOBUYUKI KITAMORI, TSUGIO SHIMAMOTO1976 Volume 24 Issue 8 Pages 1789-1794
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA study was made on the effect of dimensions on the disintegration time of tablet. The ln-ln plot of the disintegration time against the tablet thickness gave a straight line. The relation may be expressed simply by the equation, tD=KTn where tD is the disintegration time of the tablet which is compressed at a fixed pressure and has a constant diameter and thickness T, and K and n are constants. The relation expressed by this equation held good not only for directly compressed tablets but also for tablets made from granules. A tablet disintegration mechanism can be assumed by this equation. The rate of deaggregation of particles from the surface of the tablet changes with time depending upon the degree of the acceleration of deaggregation through the swelling of the disintegrant.View full abstractDownload PDF (647K) -
MASAYUKI ONDA, REIKO YABUKI, KEIJI TAKEUCHI, YAEKO KONDA1976 Volume 24 Issue 8 Pages 1795-1798
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe compounds obtained from alumina-induced reaction of 3β, 5α-diacetoxy-6-nitri-minocholestane (3) are revised as 3β-acetoxy-6-Nα-, 7α-(4) and 7β-O-(Nβ-oxido) diazoxy-cholest-5-ene (5) the basis of their spectral data. Formation pathways of the oxadiazoles (4) and (5) from the nitrimine (3) and conversion pathways of the oxadiazoles (4) and (5) into 3β-acetoxy-6-formyl-B-nor-cholest-5-ene (8) are briefly examined.View full abstractDownload PDF (446K) -
IKUO MORIGUCHI, YAYOI KANADA, KATSUICHIRO KOMATSU1976 Volume 24 Issue 8 Pages 1799-1806
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe correlations of Hansch's hydrophobic constant (log P) with van der Waals volume (Vw) and with van der Waals surface area (Aw) were studied using 60 molecules including apolar organic compounds and inert gases, and superiority of Vw over Aw was recognized. From the obtained highly significant relation of Vw to log P and a great number of log P values for polar molecules, hydrophilic effects (Vw) of various polar groups were evaluated. These parameters (Vw and Vw) could be satisfactorily applied to the regression analysis of water-solubility of 156 organic liquids and frog muscle narcosis of 39 drugs. These parameters may especially be useful for drug design because they can easily be calculated for a wide variety of molecules.View full abstractDownload PDF (728K) -
MASASHI TOMODA, SATOMI KIMURA1976 Volume 24 Issue 8 Pages 1807-1812
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPartial acetolysis of Bletilla-glucomannan, the mucilage from the tubers of Bletilla striata REICHENBACH fil., has led to the isolations of fourteen oligosaccharides. Analysis of components, methylation and partial degradation studies provided the evidences that they are O-β-D-mannopyranosyl-(1→4)-D-mannopyranose, O-α-D-mannopyranosyl-(1→4)-D-mannopyranose, O-β-D-mannopyranosyl-(1→4)-D-glucopyranose, O-β-D-glucopyranosyl-(1→4)-D-mannopyranose, O-β-D-glucopyranosyl-(1→4)-D-glucopyranose, O-β-D-mannopyranosyl-(1→4)-O-β-D-mannopyranosyl-(1→4)-D-mannopyranose, O-β-D-glucopyranosyl-(1→4)-O-β-D-mannopyranosyl-(1→4)-D-mannopyranose, O-β-D-mannopyranosyl-(1→4)-O-β-D-mannopyranosyl-(1→4)-D-glucopyranose, O-β-D-mannopyranosyl-(1→4)-O-β-D-mannopyranosyl-(1→4)-D-glucopyranose, O-β-D-mannopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→4)-D-mannopyranose, O-β-D-glucopyranosyl-O-β-D-glucopyranosyl-(1→4)-O-β-D-mannopyranosyl-(1→4)-D-mannopyranose, O-β-D-mannopyranosyl-(1→4)-O-β-D-mannopyranosyl-(1→4)-O-β-D-mannopyranosyl-(1→4)-D-mannopyranose, O-β-D-glucopyranosyl-(1→4)-O-β-D-mannopyranosyl-(1→4)-O-β-D-mannopyranosyl-(1→4)-D-mannopyranose, and O-β-D-mannopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→4)-O-β-D-mannopyranosyl-(1→4)-D-mannopyranose. Among them, it is conceivable that mannobiose having α-glycosidic linkage is the artifact produced during the reaction.View full abstractDownload PDF (745K) -
ISAO TAKEUCHI, YOSHIKI HAMADA1976 Volume 24 Issue 8 Pages 1813-1821
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1, 7-Naphthyridine (II) was prepared by the reduction of 8-chloro-1, 7-naphthyridine over palladium-carbon. 1, 5-Naphthyridine 1-oxide (III) and 1, 5-naphthyridine (IV) were synthesized by the reaction of 3-aminopyridine 1-oxide with glycerol in the presence of Sulfo-mix, ferrous sulfate, and boric acid. Phenylation of 1, X-naphthyridine (X=5, 6, 7, and 8) with phenyllithium afforded monophenylated compounds, phenyllithium having reacted in the 2-position. Methylation of II with methylsulfinyl carbanion afforded 4, 8-dimethyl-1, 7-naphthyridine (XI), and the Reissert reaction of II with benzoyl chloride and potassium cyanide afforded the normal Reissert compound (XII). Insecticidal activity of V, VIII-X, and XIII-XVIII was also examined.View full abstractDownload PDF (865K) -
MAMORU SUGIURA, MASAKAZU ISOBE1976 Volume 24 Issue 8 Pages 1822-1828
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe hydrolytic activity of the lipase (EC 3. 1. 1. 3) from Chromobacterium for the monomeric esters was found. The hydrolysis of p-nitrophenyl acetate by the lipase proceeded with three step reaction in which acylation and deacylation processes of the enzyme were involved. The rate limiting step was found to be the acylation. The enzymic hydrolysis was accelerated about 2-fold by the additions of hydrophobic glass beads. Water soluble organic solvents did not activate but inhibit the enzymic hydrolysis and they did not affect significantly on the activating effect by hydrophobic glass beads. It was found that the lipase was adsorbed on the glass beads and once adsorbed enzyme was difficult to desorb. These results were discussed relation to the reaction mechanism of lipolysis by lipase and an assumption was made.View full abstractDownload PDF (823K) -
MASAYUKI ONDA, KEIJI TAKEUCHI1976 Volume 24 Issue 8 Pages 1829-1831
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhotolysis of 3β, 5α-diacetoxy-6-nitriminocholestane (1) gives 3β, 5α-diacetoxycholestan-6-one (2), 3β-acetoxy-5α-cholestan-6-one (8), 3β, 5α-diacetoxy-6-hydroximinocholestane (9), and 3β, 5α-diacetoxy-6-iminocholestane (10) as nitrate. The structure of 10 is proved by its catalytic reduction and subsequent acetylation to 6β-acetamido-3β, 5α-diacetoxycholestane (11). The structure of 9 is identified by its reduction with titanium trichloride to 10. Also, formation pathways of these photo-products are briefly examined.View full abstractDownload PDF (429K) -
SHOZO MIYAZAKI, MASAHIRO NAKANO, TAKAICHI ARITA1976 Volume 24 Issue 8 Pages 1832-1838
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA quantitative method was described which utilized infrared spectroscopy for the determination of chlortetracycline hydrochloride (CTC-HCl) crystalline forms in mixtures. Data were included which demonstrated that the method could be utilized to follow the rate of transformation taking place in the biologically available crystalline form (β form). Transformation of the crystalline form under different conditions such as solid state and aqueous suspension was investigated. The solid CTC-HCl β form was shown to change to the more stable α form in high humidities, over 75% relative humidity (R. H.) at 20°. The rate of transformation was found to be proportional to the humidity. On the other hand, under 65% R. H. no polymorphic transformation was observed for 40 days at 20°. Transformation of the β form was also not detected by heating at 70°. In aqueous suspensions, rapid solution phase transformation was observed from the CTC-HCl β form to the water-stable α form. The rate of transformation in the suspensions was found to be temperature and pH dependent. Results obtained from these transformation studies suggested that water and water vapor were important factors in the transformation of the CTC-HCl β form.View full abstractDownload PDF (723K) -
YASUO AKITA, KEIKO MISU, TOKUHIRO WATANABE, AKIHIRO OHTA1976 Volume 24 Issue 8 Pages 1839-1841
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSN-Oxides of pyridine, quinoline, and pyrazine derivatives were reduced with chromium (II) chloride in acetone, methanol, or chloroform at room temperature to give the deoxygenation products in excellent yields. Quinaldine and 2-ethoxyquinoline 1-oxides, possessing an electron donating group at 2-position of the quinoline ring, were not reduced at room temperature, but, under reflux, the reaction gave the deoxygenation products in good yields. In the case of the reaction of 4-chloroquinoline 1-oxide with chromium (II) chloride for 20 min occured dechlorination and deoxygenation, but for 1 min only deoxygenation. The reaction of 4-nitropyridine 1-oxide and 3-, 4-, and 5-nitroquinoline 1-oxides was not successful.View full abstractDownload PDF (462K) -
HIDEO BANDO, TAKASHI YAMAGISHI, KOJI HAYASHI, HIROSHI MITSUHASHI1976 Volume 24 Issue 8 Pages 1842-1844
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new 5, 6α-glycolic compound, glycocaudatin, isolated from Cynanchum caudatum, in addition to glycocynanchogenine and 12β-O-cinnamoyl-20-O-acetyl-glycosarcostin, was identical with the derivative obtained in a good yield via the epoxidation of caudatin, which had been isolated from the same plant.View full abstractDownload PDF (459K) -
YOKI MORI, KYOKO SAITO, YASUTOSHI TONOI, HIROSHI KUMAOKA, MASUO AKAGI1976 Volume 24 Issue 8 Pages 1845-1852
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of glucose and galactose on the formation of respiratory enzymes and cytochromes in yeast cells was compared both in aerobic culture and during adaptation of anaerobically grown cells to oxygen. (1) In aerobic culture, activities of reduced nicotinamide-adenine dinucleotide (NADH) cytochrome c reductase and malate dehydrogenase and QO2 of cells were reduced considerably with increasing concentration of glucose in the medium. On the other hand, galactose did not repress NADH cytochrome c reductase significantly and QO2 of cells was not reduced with increasing concentration of gllactose in the growth medium, although it slightly repressed malate dehydrogenase. (2) Formation of cytochromes, and NADH cytochrome c reductase and malate dehydrogenase during the adaptation of anaerobic cells to oxygen were inhibited by a high concentration of glucose but not by galactose, and glucose was consumed rapidly but galactose was consumed slowly. On the other hand, when yeast cells grown anaerobically in the presence of galactose were transferred to aerobic culture in the presence of galactose, it was consumed rapidly and the formation of cytochromes, NADH cytochrome c reductase and malate dehydrogenase was inhibited. NADH ferricyanide reductase activity did not changed significantly during the adaptation of anaerobic cells to oxygen.View full abstractDownload PDF (968K) -
YUZURU YAMAMOTO, KENICHI NISHIMURA, NORIKI KIRIYAMA1976 Volume 24 Issue 8 Pages 1853-1859
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe metabolites of Aspergillus terreus IFO 6123 were studied. 3-Methylorsellinic acid, 4-O-demethylbarbatic acid and a new metabolite named asterriquinone were isolated. The chemical structure of asterriquinone was established as 2, 5-bis-[N-(1", 1"-dimethyl-2"-propenyl)-indoyl-3']-3, 6-dihydroxy-1, 4-benzoquinone by chemical and physical experimental data. The incorporation experiments using 14C-labeled compounds showed that asterriquinone is biosynthesized from tryptophan and isopentenyl unit derived from mevalonate.View full abstractDownload PDF (875K) -
HIROSHI HOSODA, KOUWA YAMASHITA, NORIKO CHINO, TOSHIO NAMBARA1976 Volume 24 Issue 8 Pages 1860-1864
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe titled compounds (1, 2) have been prepared from dehydroepiandrosterone. Introduction of the hydroxyl group into the 15α-position was attained by hydroboration of the 14, 15-double bond with diborane and subsequent oxidation of the organoborane with alkaline hydrogen peroxide under the protection of the 5, 6-double bond as the 3, 5-cyclo structure. A simple method for regeneration of the 3β-hydroxy-Δ5-steroid from the 3, 5-cyclo derivative was also developed.View full abstractDownload PDF (667K) -
HIROSHI HAMADA, YOSUKE OHKURA1976 Volume 24 Issue 8 Pages 1865-1869
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new photometric method is presented for the assay of serum glutamate pyruvate transaminase activity on the basis of the determination of 2-oxoglutaric acid produced in the enzyme reaction under its optimal conditions by means of the previously established method for selective determination of the acid with diazotized sulfamethizole. The method gives reliable results and is simply performed with a small amount of sample with a wide range of activity.View full abstractDownload PDF (633K) -
TETSUJI KAMETANI, YOSHIO KIGAWA, TAKIKO TAKAHASHI, HIDEO NEMOTO, KEIIC ...1976 Volume 24 Issue 8 Pages 1870-1878
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of 3-carboxy-1, 2-dihydro-1-methyl-2-oxopyridine (V) with diazomethane afforded 6, 7-dihydro-1, 6-dimethyl-7-oxopyrazolo [3, 4-c] pyridine (VI), 4, 5, 6, 7-tetrahydro-1, 6-dimethyl-7-oxopyrazolo [3, 4-c] pyridine (VII), and 1, 2-dihydro-3-methoxycarbonyl-1, 4-dimethyl-2-oxopyridine (VIII). 1-Ethyl-6, 7-dihydro-3, 6-dimethyl-7-oxopyrazolo [3, 4-c] pyridine (XXI), 8a-ethoxycarbonyl-1, 4, 4a, 7, 8, 8a-hexahydro-3, 4, 7-trimethyl-8-oxopyrido [3, 4-c] pyridazine (XXII), and 3-ethoxycarbonyl-4-ethyl-1, 2-dihydro-1-methyl-2-oxopyridine (XXIII) were obtained from the reaction of compound (V) with diazoethane. The treatment of 4-carboxy-1, 2-dihydro-1-methyl-2-oxopyridine (XXVIII) with diazomethane gave 1, 2-dihydro-4-methoxycarbonyl-1-methyl-2-oxopyridine (XXIX), 6-methoxycarbonyl-3-methyl-2-oxo-3-azabicyclo [4. 1. 0] hept-4-ene (XXX), and 1, 2-dihydro-4-methoxycarbonyl-1, 3-dimethyl-2-oxopyridine (XXXI). The reaction of compound (XXIX) with diazoethane afforded 3-ethyl-1, 2-dihydro-4-methoxycarbonyl-1-methyl-2-oxopyridine (XXXII), 6α-methoxycarbonyl-3, 7β-dimethyl-2-oxo-3-azabicyclo [4, 1, 0]-hept-4-ene (XXXIII), and 1-ethyl-6-methoxycarbonyl-3, 7-dimethyl-2-oxo-3-azabicyclo [4. 1. 0] hept-4-ene (XXXIV). In case of the treatment of 5-carboxy-1, 2-dihydro-1-methyl-2-oxopyridine (XXXV) and 1, 5-dihydro-1, 5-dioxo-3H-oxazolo [3, 4-a] pyridine (XXXVIII) with diazomethane, 1, 2-dihydro-5-methoxycarbonyl-1-methyl-2-oxopyridine (XXXVI) and 1, 2-dihydro-6-methoxycarbonyl-1-methyl-2-oxopyridine (XXXIX) were obtained, respectively.View full abstractDownload PDF (1079K) -
YOSHIO ARATA, SHINGO YASUDA, KENJI TOKUNO, MIYOJI HANAOKA1976 Volume 24 Issue 8 Pages 1879-1883
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe Stevens rearrangement of the N-benzyl bromide (VII), derived from 1-oxoquinolizidine (V), afforded 9a-benzyl-1-oxoquinolizidine (VIII). Reduction of the methiodides (VI and IX) of V and VIII with sodium amalgam gave the ten-membered aminoketones (XII and XIII), respectively. The yield of XIII was much more excellent than that of XII, because of the influence of the C9a-benzyl substituent in IX. The C9a-benzyl substituent, however, produced little effect on the reductive cleavage in the Birch reduction of IX leading to XIII and XV in comparison with that of VI leading to XIV, though 9a-benzylquinolizidine methiodides (XIa and XIb) furnished the ten-membered amine (XVI) in considerable yields.View full abstractDownload PDF (691K) -
SEIICHI UESUGI, TAKEO NAGURA, EIKO OHTSUKA, MORIO IKEHARA1976 Volume 24 Issue 8 Pages 1884-1892
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSUltraviolet absorption and circular dichroism properties of ApUpG and its analogs in which the adenosine is modified are reported. The adenosine analogs include formycin (F), 8, 5'-S-cycloadenosine (sA), 8, 2'-S-cycloadenosine (As), 8, 5'-O-cycloadenosine (oA), 8, 2'-O-cycloadenosine (Ao), 8-bromoadenosine (Br-A) and 8-oxyadenosine (HO-A). S-and-O-Cyclonucleosides and F take torsion angles of anti type, while Br-A and HO-A assumed to take syn conformation in these analog trinucleotides. All analogs have very weak stacking interaction and show a tendency to form an aggregate at low temperature.View full abstractDownload PDF (815K) -
TARO OGISO, KAZUNORI KUHARA, NOBUTAKA NODA, YOSHIO KATO1976 Volume 24 Issue 8 Pages 1893-1901
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn attempt has been made to clarify the action of drugs for liver disease, protoporphyrin (PP) and phosphorylcholine (PC) on the structure of liver microsomal membrane during carbon tetrachloride (CCl4) intoxication, by measuring ultraviolet (UV) absorbance, infrared (IR) spectroscopy, circular dichroism (CD) and ribonucleic acid (RNA) content, and by using some hydrophobic probes, 1-anilinonaphthalene-8-sulfonate (ANS) and 2, 4, 6-trinitro-benzenesulfonate (TNBS). Administration of PC to CCl4-poisoned rats was found to decrease the increased nonribosomal RNA content of the microsomes at 5 days, to some extent. ANS binding to microsomes little changed in all groups. A double reciplocal plot of ANS binding to the microsomes indicated that the affinity of the membrane of all groups for ANS was not affected by CCl4 or the drug administrations. TNBS binding to the amino-phospholipids, phosphatidylserine (PS) and phosphatidylethanolamine (PE), however, on the membrane was extremely decreased in CCl4-poisoned rats at 2 and 5 days, by 21-25% for PS and 25-34% for PE, as compared with those of control rats, indicating a significant alteration of the phospholipid composition in the membrane. Administration of PC for 8 days produced a significant increase in its binding to both aminophospholipids. It was found from CD spectra of the membrane that CCl4 administered caused partially conformational changes of the proteins, significant at 5 days, and administration of PC to the poisoned rats for 5 days recovered the decreased ordered structure to the nativelevel. A semigraphical method of CD data analysis exhibited that the membrane contained approximately 55% α-helix, 21% β-structure and 24% unordered structure and CCl4 administration decreased the helix content by 9% without significant alteration of β-structure. IR spectra also indicated that the membrane contained β-structure. PP had no appreciable effects on the structure of the membrane. Thus, it is concluded that PC has an excellent reconstructive action of phospholipid and protein structure of the injured microsomal membrane.View full abstractDownload PDF (1028K) -
KOJI YAMAKAWA, HAJIME KANEOYA1976 Volume 24 Issue 8 Pages 1902-1908
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSUnsymmetrical β-diketonate metal (III) chelates, tris (formylacetonato) cobalt (III) and-chromium (III) chelates, were synthesized. Fac and mer isomers of these chelates were separated by column chromatography, and the stereochemistry of paramagnetic cobalt (III) chelate is discussed from nuclear magnetic resonance (NMR) spectra. Electrophilic substitution reactions (chlorination, bromination, iodination, nitration, and thiocyanation) of the fac and mer isomers of these chelates were successful. Infrared, ultraviolet, and NMR spectra were measured for these chelates.View full abstractDownload PDF (828K) -
JOHJI YAMAHARA, TAKAO KONOSHIMA, YAYOI SAKAKIBARA, MAKIKO ISHIGURO, TO ...1976 Volume 24 Issue 8 Pages 1909-1912
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTetrahydropalmatine is known to have potent sedative and hypnotic action and the depressant effect on the central nervous system of some compounds to realted berberine was tested. The levorotatory isomer of tetrahydroberberine had a stronger activity among the synthesized compounds.View full abstractDownload PDF (502K) -
TAKEKI OKUMOTO, HIROSHI IMAMURA1976 Volume 24 Issue 8 Pages 1913-1916
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSImprosulfan had the topical antitumor activity against Yoshida sarcoma cells, in comparison with cyclophosphamide. The mean survival time of rats bearing the tumor treated intraperitoneally with each optimal dose of improsulfan (10 mg/kg/day) or cyclophosphamide (5 mg/kg/day) from day 3 for 2 weeks was 32.2 or 31.7 days, respectively. In the sequential treatment of the two drugs, the mean survival time of the group administered with improsulfan for the first week and with cyclophosphamide for the second week was 46.3 days, which was the longest day among all of the groups tested. The therapeutic effect may be improved even by combinations of alkylating agents.View full abstractDownload PDF (544K) -
KEITARO SENGA, YUKAKO KANAMORI, SADAO NISHIGAKI, FUMIO YONEDA1976 Volume 24 Issue 8 Pages 1917-1921
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new synthetic method of 2-vinyl-v-triazolo [4, 5-d] pyrimidines, which consists of the nitrosative cyclization of 1, 3-dimethyl-6-(α-methylalkylidenehydrazino) uracils with a mixture of N-nitrosodimethylamine and phosphorus oxychloride (NDA+POCl3) is described. The reaction of 1, 3-dimethyl-6-hydrazino-5-nitrosouracil with acetophenone gave 1, 3-dimethyl-6-phenyl-7-azalumazine (3-phenylfervenulin) (X). The nitrosation of 6-benzylidenehydrazino-1, 3-dimethyluracil with NDA+POCl3 also gave X.View full abstractDownload PDF (583K) -
HIROSHI HARA, OSAMU HOSHINO, BUNSUKE UMEZAWA1976 Volume 24 Issue 8 Pages 1921-1925
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBy the treatment of the p-quinol acetate (Xa) and (Xb) with trifluoroacetic acid, (±)-10-benzyloxy-1-hydroxy-2, 9-dimethoxyaporphine (XIa) and (±)-9-benzyloxy-1-hydroxy-2, 10-dimethoxyaporphine (XIb) were given in good yield, respectively. Furthermore, XIa and XIb were converted to (±)-bracteoline (XIIa) and (±)-isoboldine (XIIb) by catalytic debenzylation, or to (±)-10-hydroxy-1, 2, 9-trimethoxyaporphine (XIVa) and (±)-N-methyllaurotetanine (XIVb) by methylation and successive debenzylation, respectively.View full abstractDownload PDF (720K) -
YOSHIO OKADA, SHOHEI TANI, YUKO YAWATARI, MASAMI YAGYU1976 Volume 24 Issue 8 Pages 1925-1927
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs analogues of D-cycloserine, the part structure of penicillin and D-D carboxypeptidase substrate of peptidoglycan of bacterial cell wall, D-alanine derivatives and their stereoisomers and D-alanyl-D-alanine derivatives and their stereoisomers (R1-Ala-R2, R1-Ala-Ala-R2 : R1=Z, H ; R2=NHNH2, NHCH3, NHCH2CH2OH) were synthesized. All compounds obtained did not show any antibacterial activity against Staphylococcus aureus, Sarcina lutea, Pseudomonas aeruginosa and Escherichia coli.View full abstractDownload PDF (502K) -
TORU TAKESHITA, SACHIO ISHIMOTO, NOBUO IKEKAWA1976 Volume 24 Issue 8 Pages 1928-1931
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDesmosteryl acetate, a useful key intermediate for synthesis of the metabolites of vitamin D3, was synthesized from fucosterol by two routes ; (1) 24, 28-epoxyfucosteryl acetate was treated with solid acids such as zeolite, silica-alumina and alumina-boria to give desmosteryl acetate in a yield of 16%-40%, (2) dehydration of 24-hydroxycholesteryl acetate, which was obtained by ozonolysis of fucosteryl acetate followed by reduction with sodium borohydride, with P2O5 in benzene afforded desmosteryl acetate in a yield of 85%.View full abstractDownload PDF (542K) -
KOJI YAMAKAWA, HAJIME KANEOYA1976 Volume 24 Issue 8 Pages 1931-1934
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIntroduction of chlorine, bromine, and iodine atom into the ring of labile bivalent metal acetylacetonates, bis (acetylacetonato) nickel (II) and-cobalt (II) chelates, is effected by N-halosuccinimide in carbon tetrachloride. Infrared and ultraviolet spectra of halogenated metal (II)-acetylacetonate chelate derivatives were measured. The masses of substituent at the central carbon atom of these metal (II)-acetylacetonates affected the frequencies of C=O and C=C stretching bands.View full abstractDownload PDF (567K) -
HAJIME KANEOYA, KOJI YAMAKAWA1976 Volume 24 Issue 8 Pages 1934-1935
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of bis (o-phenylenediamine) nickel (II) chloride and acetylacetone is examined and bis (acetylacetonato) (o-phenylenediamine) nickel (II) chloride dihydrate and 2, 4-dimethyl-1, 5-benzodiazepinium chloride were isolated.View full abstractDownload PDF (365K) -
TOSHIAKI MORIMOTO, MINORU SEKIYA1976 Volume 24 Issue 8 Pages 1935-1938
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIt has now been found that trichloroacetyl chloride is capable to react with Schiff bases in the presence of triphenylphosphine to give 3, 3-dichloro-2-azetidinones. Mechanistically the reaction appears to involve the chlorine cation extraction from the initially formed adduct by triphenylphosphine.View full abstractDownload PDF (515K) -
YASUO KIKUGAWA, YUUSAKU YOKOYAMA1976 Volume 24 Issue 8 Pages 1939-1943
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSodium acetanilidoborohydride prepared from acetanilide and sodium borohydride in α-picoline reduced acid chlorides to alcohols in dichloromethane. On the other hand, this reducing reagent prepared in pyridine did not reduce acid chlorides but reduced the pyridine ring to give acylpiperidines.View full abstractDownload PDF (653K) -
SHUNICHI NAITO, KIYOKO SHIODA, MACHIKO SAWADA, SHOKO NIKI, MIKIO AWATA ...1976 Volume 24 Issue 8 Pages 1943-1947
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe laxative action of bis (p-hydroxyphenyl) pyridyl-2-methane disulfate is considered to be dependent on the formation of the free phenolic compound, bis (p-hydroxyphenyl)-pyridyl-2-methane by hydrolysis. Therefore, the activity of the parent compound as a laxative must be governed by arylsulfatase activity in the human intestine. When examinations of human feces were made, arylsulfatase activity in the intestine was detected, and about 98% of the samples were shown to be positive. Validity of the fecal arylsulfatase test in the test population might be supported by the liquefaction test of rat feces with the injection of the parent compound into duodenum.View full abstractDownload PDF (600K) -
MASUO MORISAKI, KIYOSHI BANNAI, NOBUO IKEKAWA1976 Volume 24 Issue 8 Pages 1948-1949
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOxymercuration-demercuration of 3β-acetoxycholesta-1, 5-diene (2) followed by saponification gave 2β-hydroxycholesterol (3) and 1α-hydroxycholesterol (4) in 14% and 26% yield, respectively.View full abstractDownload PDF (383K) -
DAISUKE SATOH, TOSHIHIRO HASHIMOTO1976 Volume 24 Issue 8 Pages 1950-1953
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReduction of 16-anhydrogitoxigenin 3-acetate (II) with NaBH4-transition metal chloride systems as well as with transition metal hydrides gave geometrically isomeric card-17 (20)-enolides, V and VI, new type of cardenolide. Stereochemistry of the products was discussed on the basis of Cotton effect, 1H-and 13C-nuclear magnetic resonance spectra. The structure and ratio of the products varied depending on the kind of transition elements.View full abstractDownload PDF (446K) -
KEIICHI TANIKAWA1976 Volume 24 Issue 8 Pages 1954-1956
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA difference in detection sensitivity of β-diketone metal chelates by gas chromatography is produced by the difference in the metal present, irrespective of the difference in ligands or of detectors and the reason for it was examined by gas chromatography-mass spectrometry (GC-MS). When the chelates of copper (II) and iron (III), which show poor sensitivity in gas chromatography, were introduced directly into the ion source of a mass spectrometer, their ionic intensity was large but the ratio of molecular ion to total ion was smaller than that of the chelates of rhodium (III) and chromium (III), which show good detection sensitivity. When the sample was heated for gasification and collected in a gas reservoir for mass spectrometry, chelates of copper (II) and iron (III) showed great disintegration of the molecular ion and a large number of fragment ion species was produced. Ratio of molecular ions to total ions was greater in rhodium (III) and chromium-(III) chelates, with smaller number of fragment ions. Thus the difference in detection sensitivity according to the kind of a metal present was related to the ratio of molecular ions present to total ions of the metal chelates, and the difference in the detection sensitivity of β-diketone metal chelates in gas chromatography is affected largely by thermal stability of the chelates rather than by ionization efficiency of flame ionization detector and electron caputure ionization detector or to the stability of these chelates to ionization.View full abstractDownload PDF (503K) -
EIICHI YOSHII, TORU KOIZUMI, TOSHIJI KAWAZOE1976 Volume 24 Issue 8 Pages 1957-1958
Published: August 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSKetene triethylsilyl methyl acetals obtained by hydrosilation of α, β-unsaturated esters were reacted with phenyl (bromdichloromethyl) mercury to give homologated 2-chloroacrylatesView full abstractDownload PDF (361K)