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Volume 100, Issue 3
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KITARO OKA1980 Volume 100 Issue 3 Pages 227-240
Published: March 25, 1980
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSSynthetic studies on salamander alkaloids isolated from animal venom in the skin gland of Salamandra maculosa LAURENTI were performed. Syntheses of three groups of alkaloids, one with a bicyclo-oxazolidine, one with a carbinolamine, and another with a pure 3-aza-A-homo steroid, are discussed. Regio- and stereospecific syntheses of the alkaloids are discussed in connection with the construction of the bicyclo-oxazolidine system of the major alkaloids and in connection with Beckmann rearrangement of steroid 3-ketoximes for the syntheses of the other alkaloids. A theoretical approach to the resolution of the geometrical isomers of oximes by adsorption chromatography is also discussed.View full abstractDownload PDF (1044K) -
KAZUO KIGASAWA, HIROAKI SHIMIZU, MORIHIRO SAITO, TOSHIHIRO HAYASHI, MA ...1980 Volume 100 Issue 3 Pages 241-248
Published: March 25, 1980
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe serum concentration of unchanged pentazocine (PA) was investigated in rabbits when PA was administered concurrently with acetaminophen, salicylamide (SAM), salicylic acid, acetylsalicylic acid, or p-aminosalicylic acid. The serum concentration of unchanged PA increased when 20 mg/kg PA was administered concurrently with 80 mg/kg SAM as compared with the administration of 20 mg/kg PA alone, but no similar results were obtained with the other drugs. The co-administration of PA and SAM also decreased serum and urinary PA glucuronide. On the other hand, when 80 mg/kg SAM and 375.6 mg/kg PA were administered together, the serum and urinary concentration of unchanged SAM was increased, while SAM glucuronide was decreased. We posit that the effect noted in the simultaneous 20 mg/kg PA and 80 mg/kg SAM administration experiments is due to competitive inhibition of glucuronidation.View full abstractDownload PDF (949K) -
KAZUO KIGASAWA, HIROAKI SHIMIZU, MORIHIRO SAITO, TOSHIHIRO HAYASHI1980 Volume 100 Issue 3 Pages 249-255
Published: March 25, 1980
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe glucuronidations of pentazocine (PA) and salicylamide (SAM) were investigated in the microsomes of rabbit liver and the small intestine. 1) PA glucuronidation was inhibited competitively by the addition of SAM. 2) The inhibitory effect on PA glucuronidation was found to be greater with the addition of o-, m- or p-nitrophenol, and lesser with the addition of SAM and o-aminophenol. Salicylic acid, p-aminosalicylic acid or gentisic acid showed only slight inhibitory effect, and acetaminophen showed no effect. 3) It appeared that the degree of inhibition of PA glucuronidation by the addition of one of the phenolic compounds was almost the same in the liver and small intestine.View full abstractDownload PDF (692K) -
HIROSHI KASHIWAGI, SABURO ENOMOTO1980 Volume 100 Issue 3 Pages 256-261
Published: March 25, 1980
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSA search for catalysts effective for the ammoxidation of o-, m-, and p-methylanisole was undertaken. When a mixture of V2O5-ZrO2 (wt ratio of 8 : 2) was used, o-methyl-anisole was converted to o-methoxybenzonitrile with a conversion of 48% and a selectivity of 55% (380°), m-methylanisole was converted to m-methoxybenzonitrile with a conversion of 49% and a selectivity of 41% (410°), and p-methylanisole was converted to p-methoxy-benzonitrile with a conversion of 64% and a selectivity of 51% (380°). A catalyst with a large V2O5 content showed an initially large catalytic activity which, however, deteriorated rapidly. High selectivity to methoxybenzonitrile was observed at small partial pressure of methylanisole. Catalytic activity was not very sensitive to the partial pressure of ammonia, but was very sensitive to the partial pressure of oxygen. For example, very rapid deterioration of catalytic activity was observed at small partial pressure, and considerable oxidation reaction was observed at a large partial pressure of oxygen. Time-and temperature dependence of the selectivity of the reaction products of ammoxidation of p-methylanisole were discussed.View full abstractDownload PDF (640K) -
TAKAKO HORI, CHOSAKU YOSHIDA, YASUO KIBA, JOJI NAKANO, SUMIKO KISHIMOT ...1980 Volume 100 Issue 3 Pages 262-271
Published: March 25, 1980
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe 1, 4-benzoquinone derivatives I, II and III (Chart 1) were synthesized. In the synthesis of I (m=0), a new reaction was found, in which 1, 4-benzoquinones reacted with 1-trimethylsilyl-4-substituted-2, 3-dioxopiperazine derivatives to yield 2-(4-substituted-2, 3-dioxo-1-piperazinyl) hydroquinones. In this reaction, the substituent effect was investigated and the reaction mechanism was discussed. Compound II of this series showed antitumor activity against L1210 and S180.View full abstractDownload PDF (954K) -
KAZUKI TAIRA, YUKIHIRO YASUDA, TAKASHI SHINDO, NARUO MITANI, AKIRA AKA ...1980 Volume 100 Issue 3 Pages 272-279
Published: March 25, 1980
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe biological fate of 4-butyl-4-(β-carboxypropionyloxymethyl)-1, 2-diphenyl-3, 5-pyrazolidinedione : suxibuzone (SB) was studied in rats and beagle dogs. Furthermore, the effects of SB on liver microsomal drug metabolizing enzyme systems in rats were compared with those of phenylbutazone (PB), after daily oral administration of SB or PB for 1 week. 1) The biological fate of SB was different in rats and dogs and in the former a sex difference was noted. 2) Liver microsomal drug metabolizing enzyme systems were induced especially in male. 3) No difference between the two drugs was noted. However, when a single oral dose of SB was administered, keeping the PB schedule the same as above, the plasma half-life of PB was markedly shortened and maximum plasma levels of metabolites were rapidly reached. These results suggest that the biological fate of SB was stimulated by the enhancement or induction of liver microsomal drug metabolizing enzyme systems due to PB and its metabolites after daily oral administration.View full abstractDownload PDF (705K) -
TAKESHI KATO, KIYOHISA KAWAI, YOICHI SAWA1980 Volume 100 Issue 3 Pages 280-288
Published: March 25, 1980
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSIn a search for new synthetic non-narcotic analgesics, the reduction of 2-aminomethyl-3-anilino-2-cyclohexen-1-ones (I) which had both analgesic and narcotic activities was studied. 2-Aminomethyl-3-anilinocyclohexanols (IV), (6-anilino-1-cyclohexenyl) methyl-amines (VI) and (2-anilinocyclohexyl) methylamines (VIII) were obtained by reduction of the corresponding I with lithium aluminum hydride. Configurations of IV and VIII were determined by analysis of the NMR spectra of IV, VIII and their acyl derivatives. 3-(2-Chloroanilino)-5, 5-dimethyl-2-piperidinomethylcyclohexanol (IVc) exhibited the most potent analgesic activity among the compounds synthesized. However, it was impossible to separate the analgesic from the narcotic activities in these compounds.View full abstractDownload PDF (923K) -
SHUJIRO GOYA, AKIRA TAKADATE, TOSHIAKI TANAKA, FUMIKO NAKASHIMA1980 Volume 100 Issue 3 Pages 289-294
Published: March 25, 1980
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESS7-Methoxycoumarin-4-carbonyl chloride (1), 7-methoxycoumarin-4-carbohydrazide (2), 4-methylcoumarin-7-isothiocyanate (3), and 7-dimethylamino-4-methylcoumarin-3-isothiccyanate (4) were synthesized to examine their reactivities with various functional groups and the fluorescence characteristics of the resulting derivatives. The reaction of 1 with alcohols and amines readily yielded the esters and the amides respectively. The hydrazones were obtained by the reaction of 2 with carbonyl compounds, and 3 and 4 reacted with amines to yield the thioureides. The fluorescence spectra and the quantum yields of these coumarin derivatives were measured, and it was found that 1 was useful as a fluorescent acylating reagent for alcohols and primary amines. The thioureides derived from 4 also showed a high quantum fluorescence yield.View full abstractDownload PDF (626K) -
TOMOHIKO YOSHIDA, HIROKAZU TANIGUCHI, TAKAKO YOSHIDA, SABURO NAKANO1980 Volume 100 Issue 3 Pages 295-301
Published: March 25, 1980
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSA fluorometric method for the determination of p-aminophenol (AP) with 3-amino-2 (1H)-quinolinethione (AQT) was described. AP was oxidized with ceric ammonium sulfate dihydrate and allowed to react with AQT in the presence of a small amount of hydrogen peroxide in a dilute sulfuric acid solution. In an alkaline solution, the reaction product developed a yellow green fluorescence which had an excitation maximum at 394 nm and an emission maximum at 530 nm. The fluorescence intensity was linear over the range 0.5-4.5μg/ml of AP. On the other hand, acetaminophen (AAP) was hydrolyzed to AP in a dilute sulfuric acid solution, and 0.5-6.0μg/ml of AAP was determined by the same method as AP. The coefficients of variation were 1.0% (n=10) and 1.2% (n=10) for 3.0μg/ml of AP and AAP, respectively. The fluorometric method for AAP was applicable to the determination of AAP in anti-cold pharmaceutical preparations.View full abstractDownload PDF (568K) -
SHIGERU KOBAYASHI, MASARU KIHARA, TETSURO SHINGU1980 Volume 100 Issue 3 Pages 302-306
Published: March 25, 1980
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSPhotolysis of the hydrochloride of 2-iodo-N-(2-iodobenzyl)-β-phenethylamine (9) gave the apogalanthamine analogs, 5, 6, 7, 8-tetrahydrodibenz [c, e] azocine (1), 9-iodo-, and 4-iodo-5, 6, 7, 8-tetrahydrodibenz [c, e] azocines (10 and 11, respectively).View full abstractDownload PDF (639K) -
TOSHIKO UTAMURA, KYOKO KOIZUMI1980 Volume 100 Issue 3 Pages 307-312
Published: March 25, 1980
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe 13C-NMR spectra of methyl 6-and 6'-O-trityl-β-cellobiosides in pyridine-d5 were recorded, and their signals were assigned by comparison of their spectra and those of methyl β-D-glucopyranoside, methyl 6-O-trityl-β-D-glucopyranoside, methyl 4-O-methyl-β-D-glucopyranoside, and methyl 4-O-methyl-6-O-trityl-β-D-glucopyranoside. On the basis of tritylation and β-D-glucosidation shifts estimated from the 13C chemical shifts of these compounds, the effects of 6- and 6'-O-tritylations upon the conformation around the inter-glycosidic linkage of the cellobioside are discussed.View full abstractDownload PDF (632K) -
KENICHI YAKUSHIJIN1980 Volume 100 Issue 3 Pages 313-318
Published: March 25, 1980
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSReaction of 1-phenylfuro [2, 3-c] isoquinolin-5 (4H)-one (IIIa) with acetyl nitrate and bromine in the presence of ethanol or water gave 1, 2, 3, 4-tetrahydroisoquinolines (IV and VI). 5-Chloro-1-phenylfuro [2, 3-c] isoquinoline-2-carbaldehyde (VII) was obtained from the Vilsmeir formylation of IIIa and 5-chloro-1-phenylfuro [2, 3-c] isoquinoline (VIII). Nitration of VIII with acetyl nitrate gave 5-chloro-2-nitro-1-phenylfuro [2, 3-c] isoquinoline (IX) and 2, 5-dichloro-1-phenylfuro [2, 3-c] isoquinoline (X). 3-Alkyl-7-phenylfuro [2, 3-c]-sym-triazolo [3, 4-a] isoquinolines (XIIIa-c) and Shiff's bases (XIVa-c) were prepared from the condensation of 5-hydrazino-1-phenylfuro [2, 3-c] isoquinoline (XII) with aliphatic acids and aromatic aldehydes.View full abstractDownload PDF (616K) -
TOSHIO MASHIKO, SHIRO TERASHIMA, SHUNICHI YAMADA1980 Volume 100 Issue 3 Pages 319-327
Published: March 25, 1980
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSBecause of the increasing importance of optically active epoxides in biological and pharmaceutical chemistry as well as in organic syntheses, the asymmetric epoxidation reaction was selected from less-developed asymmetric oxidation reactions, and the possible exploitation of the asymmetric epoxidation catalysts was investigated. Two types of the chiral molybdenum (VI) catalysts (1 and 2) involving optically active N-alkyl-β-aminoalcohols (9 and 10) as stable chiral ligands and acetylacetone as a replaceable bidentate ligand, were designed, based on the proposed mechanism for the epoxidation of allylic alcohols with alkyl hydroperoxides which could be catalyzed by metal complexes. Although attempted preparations of the former metal complexes (1) were unsuccessfull, the latter molybdenum (VI) complexes (2b-d) were successfully synthe-sized by the ligand exchange reaction of molybdenum dioxyacetylacetonate [MoO2 (acac)2] (3) with (1R, 2S)-N-alkylephedrines (10b-d).View full abstractDownload PDF (867K) -
TOSHIO MASHIKO, SHIRO TERASHIMA, SHUNICHI YAMADA1980 Volume 100 Issue 3 Pages 328-336
Published: March 25, 1980
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe catalytic asymmetric epoxidation of allylic alcohols (2a-c) with alkyl hydro-peroxides (4a, b) was attempted using chiral oxidation catalysts, (acetylacetonato)-[(1R, 2S)-N-alkylephedrinato] dioxomolybdenum (1a-c). Examination of factors, including reaction temperature, solvent, nature of oxidants, and amount of catalyst, which may affect both the chemical and optical yields of optically active 2, 3-epoxy alcohols (3a-c), resulted in the establishment of the optimal reaction condition for asymmetric epoxidation. Based on these results, the preparation of 3a-c having a (2R)-configuration was achieved with a maximum optical yield of 33% ee. The absolute configurations and optical purity of 3a-c were determined by chemical correlation with (R)-3-methylbutane-1, 2, 3-triol (8), (R)- and (S)-linalool (11 and 14), respectively. The epoxidation mechanism is discussed in detail.View full abstractDownload PDF (863K) -
JUNICHI KUNITOMO, YOSHIKO MURAKAMI, MICHINORI AKASU1980 Volume 100 Issue 3 Pages 337-341
Published: March 25, 1980
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSAir oxidation of dehydroaporphines (Ia, Ib, Ic) with alkali catalyst gave corresponding 7-oxo (IIa, IIb, IIc), 4, 5-dioxo derivatives (IIIa, IIIb, IIIc) and N-methylaristolactamtype substances (IVa, IVb, IVc) in a low yield. The structure of"1, 2, 10-trimethoxy-oxoaporphine"thought to be one of the products of the sodium-liquid ammonia reduction of dehydrothalicarpine, was found to be 2, 10-dimethoxy-4, 5-dioxodehydroaporphine (IIIa). The structure of 4, 5-dioxodehydronantenine (IIIc) from Nandina domestica THUNB. was confirmed.View full abstractDownload PDF (609K) -
TEISUKE OKANO, TAKASHI HORIE, HIROKO OHARA, NOBORU MOTOHASHI1980 Volume 100 Issue 3 Pages 342-346
Published: March 25, 1980
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSWe examined the photodynamic action of 6-mercaptopurine on calf thymus DNA and the mechanisms involved in this reaction. When the aqueous mixture of 6-mercapto-purine and DNA was irradiated by light from a 290 nm distance, the melting point and viscosity of DNA decreased, the alkaline sucrose density gradient centrifugation pattern of DNA shifted towards the less dense side, and malonaldehyde was produced in the reaction mixture. These changes were inhibited when the reaction mixture was degassed, or when a quencher for singlet oxygen or excited triplets was added to the reaction mixture. We concluded that single-chain scission of the DNA molecule occurred as a result of the photodynamic action of 6-mercaptopurine, and that singlet oxygen produced in the reaction mixture played an important role in the photosensitization of DNA.View full abstractDownload PDF (603K) -
KIYOSHI YAMADA, RYOZO KOSHIURA, KENICHI MIYAMOTO, FUJIKO SANAE1980 Volume 100 Issue 3 Pages 347-354
Published: March 25, 1980
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe pharmacological properties of DL-1-(γ-chloropropyl)-2-chloromethylpiperidine hydrobromide (CAP-2), a new nitrogen mustard type antitumor agent, were investigated in various experimental animals. The LD50 value by intraperitoneal single injection of CAP-2 was 60.0 mg/kg for female mice and 65.0 mg/kg for male mice 7 days after injection. Female and male received a maximum tolerated dose of 30 mg/kg and 25 mg/kg, respectively, of CAP-2 intraperitoneally once a day for 7 days. Decrease of spontaneous motalities, mild prolongation of sleeping time, hypothermia, and analgesic action were observed by intraperitoneal injection in mice of a dose of 30 mg/kg of CAP-2, but not at smaller doses. In the isolated large intestine of the guinea pig, a low concentration of CAP-2 caused relaxation and a decrease of activity which was antagonistic for acetylcholine, but not for barium chloride. Intestinal relaxation disappeared and changed to intestinal contraction by the repeated application of CAP-2 (1×10-4g/ml). CAP-2 (1×10-4g/ml) caused intestines relaxed by atropine to contract and increased their activity. This contraction was inhibited by paraverine. In the isolated heart of the frog, CAP-2 showed a negative inotropic action and a concentration of 1×10-4g/ml inhibited the diastric standstill by acetylcholine. CAP-2 did not affect femoral vessel flow in the frog even at a concentration of 3×10-2g/ml. CAP-2 tended to contract the rectus abdominis muscle of the frog. In the rabbit, CAP-2 (1-5mg/kg, i.v.) exhibited a temporary hypotensive action and weak respiratory stimulation. From these results, it was confirmed that CAP-2 has a depressant effect on the central nervous system and an anticholinergic action on the peripheria.View full abstractDownload PDF (959K) -
YOSHIHISA TANABE, ATSUKO KITA1980 Volume 100 Issue 3 Pages 355-358
Published: March 25, 1980
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESS1β-O-Cinnamoyl-D-glucopyranose and 1β-O-cinnamoyl-6-O-(γ-hydroxy-α-methylene-butyroyl)-D-glucopyranose were isolated from the summer leaves of Spiraea thunbergii SIEB. and their structures were elucidated. The latter is a new compound and was given the name spirarin.View full abstractDownload PDF (505K)
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