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Volume 21, Issue 5
Displaying 1-43 of 43 articles from this issue
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GORO KOBAYASHI, YOSHIRO MATSUDA, REIKO NATSUKI1973 Volume 21 Issue 5 Pages 921-925
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of α, α'-dimethylthiomethylene-2-pyridylacetonitrile (I) and active methylene compounds in dimethyl sulfoxide, in the presence of potassium carbonate, afforded 1-cyano-2-methylthio-4H-quinolizin-4-ones with the corresponding substituent in 3-position. Reaction of some of these 3-substituted compounds with benzylamine produced 2-benzylamino-1-cyano-4H-quinolizin-4-ones. Reduction of one of the 3-substituted compound over Raney nickel catalyst gave 1-cyano-3β-pyridyl-4H-quinolizin-4-one.View full abstractDownload PDF (550K) -
FUMIO YONEDA, YOSHIHARU SAKUMA, MICHIKO UENO, SADAO NISHIGAKI1973 Volume 21 Issue 5 Pages 926-930
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1, 3-Dimethyl-4-thio-7-azalumazine derivatives (5-thiofervenulins) and 1, 3-dimethyl-4-thio-6-azalumazine derivatives (5-thioisofervenulins) were synthesized by the thiation of 1, 3-dimethyl-7-azalumazine derivatives (fervenulins) and 1, 3-dimethyl-6-azalumazine derivatives (isofervenulins). The 1, 3-dimethyl-4-thio-6-azalumazines were converted into theophyllines by treatment with sodium dithionite in formic acid. These thio-azalumazines displayed low antibacterial activities in vitro.View full abstractDownload PDF (595K) -
SATOSHI OMURA, AKIRA NAKAGAWA, HARUKI YAMADA, TOJU HATA, AKIO FURUSAKI ...1973 Volume 21 Issue 5 Pages 931-940
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of new antibiotics, Kinamycin A, B, C, and D which are mainly effective against gram-positive bacteria, were extracted with chloroform from the broth filtrate of Streptomyces murayamaensis sp. nov. HATA et OHTANI. Kinamycin C (I), C24H20O10N2, m/e 496 (M+), was determined to have an 8-hydroxynaphthoquinone skeleton, nitrile, acetoxyl, and tertiary methyl groups from its ultraviolet (UV), infrared (IR), and nuclear magnetic resonance (NMR) spectra, and was further found to have a unique structure of N-C-N from some chemical reactions and X-ray diffraction. Structure relationship among I and other components A, B, and D was assumed to be due to the difference in the number and position of the acetoxyl group from analyses of IR, NMR, and mass spectra of their acetylated compounds. The antimicrobial activity of the four kinamycins increases with the decreasing number of acetoxy group, in the order of kinamycin C, A, D, and B. In addition, some derivatives obtained during structural studies on I were found to have nearly equal or increased antimicrobia1 activity compared with I and kinamycin D (XI).View full abstractDownload PDF (1108K) -
SHIGERU KOBAYASHI1973 Volume 21 Issue 5 Pages 941-951
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of compounds possessing the pyrazolo[3, 4-d]pyrimidine nucleus were synthesized, characterized and screened for the ability to inhibit xanthine oxidase activity. The compounds were compared with 4-hydroxypyrazolo[3, 4-d]pyrimidine (4), which showed 100% inhibition at a 33 μmole concentration. The structure-activity relationships of the synthesized compounds were discussed. 4-Amino-6-hydroxy-3-phenyl-pyrazolo[3, 4-d]pyrimidine (30b) and 4-amino-3-(p-chlorophenyl)-6-hydroxypyrazolo[3, 4-d]pyrimidine (30c) were found to be as potent inhibitors as allopurinol.View full abstractDownload PDF (1161K) -
TAIJU KURAMOTO, HIROSATO KIKUCHI, HIROSHI SANEMORI, TAKAHIKO HOSHITA1973 Volume 21 Issue 5 Pages 952-959
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBile salts of six different species of the Anura were investigated by means of thin-layer chromatography, gas-liquid chromatography, and mass spectrometry. Bile of Xenopus laevis contained taurine-conjugated and free forms of 3α, 7α, 12α-trihydroxy-5β-cholestanoic acid and 5β-cyprinol sulfate2) as its chief constituents. Smaller amounts of cholic acid and chenodeoxycholic acid were also detected in the hydrolyzed bile. Neither conjugated bile acids nor bile alcohol sulfates were found in the bile of Bombina orientalis, the chief constituents of which were free 3α, 7α, 12α-trihyboxy- and 3α, 7α, 12α, 24-tetrahydroxy-5β-cholestanoic acids. Hyla arborea japonica contained 5β-ranol sulfate as almost the only bile salt. Rana brevipoda contained taurine-conjugated and free forms of cholic acid and 3α, 7α, 12α-trihydroxy-5β-cholestanoic acid, and 5β-cyprinol sulfate. Rana rugosa had mainly 5α-cyprinol sulfate in its bile. There was also a minor amount of tauro-3α, 7α, 12α-trihydroxy-5α-cholestanoate. Rana limnocharis limnocharis contained taurine-conjugated and free forms of cholic acid and 3α, 7α, 12α-trihydroxy-5β-cholestanoic acid, and 5β-bufol sulfate.View full abstractDownload PDF (998K) -
NORIYASU HIROSE, SHIGERU SOHDA, SHIZUO KURIYAMA, SHOJI TOYOSHIMA1973 Volume 21 Issue 5 Pages 960-971
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThirty one derivatives of 3-alkoxy-1[ω-(N-substituted amino)-3-phenylindolin-2-one and related compounds were synthesized for pharmacological testing. As a preliminary screening test compounds were tested for analgetic-antiphlogistic activity by anti-writhing test in mice. Acute toxicity and gross behavioral changes in mice were also determined. The majority of the compounds produced anti-writhing activity.View full abstractDownload PDF (1267K) -
KEISUKE SHIGEZANE, TOMISHIGE MIZOGUCHI1973 Volume 21 Issue 5 Pages 972-980
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSModifications were attempted on the renin inhibitors, leucylleucylvalyltyrosine ethyl ester or leucylleucylvalylphenylalanine ethyl ester which were reported in the preceding paper. Borohydride reduction of the above peptide esters, prepared by the solid phase method using bromoacetyl polystyrene, afforded the respective C-terminal carbinol derivatives, which were moderately soluble in water and the renin inhibitory activity was found to be retained. Elongation of the aforementioned tetrapeptide esters or carbinols by a hydrophilic amino acid residue or introduction of the sodiumsulfomethyl group was rather fruitless with regards to solubility as well as to renin inhibitory activity. Octapeptide-carbinol derivative, prolylphenylalanylhistidylleucylleucylvalyltyrosyl-serinol was synthesized, whose dihydrochloride was moderately soluble in water and exhibited the highest renin inhibitory activity among the compounds tested throughout this series of work.View full abstractDownload PDF (1363K) -
YOUICHI SHIOKAWA, SADAO OHKI1973 Volume 21 Issue 5 Pages 981-988
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCycloaddition reactions of 2-azido-1-methylbenzimidazole (I) with such reagents as diphenylketene, dimethyl acetylenedicarboxylate, methyl propiolate, and N, N-diethyl-phenylethynylamine were investigated. The diester exclusively reacted with the carbonnitrogen double bond of imidazole ring to give the 1 : 1 molar adduct (IV). On the other hand, the ynamine added to azido group at C2-position and only triazole derivative (XI) was obtained. For thermal decomposition of the adduct (XI), the presence of 2-azirine compound (XIX), a four electron system, as intermediate was assumed from consideration of structures of the decomposition products (XII and XIII). Reaction of I with the ester gave a mixture of the triazolo derivative (VI) as major product and the 1 : 1 molar adduct (VII). Also, diphenylketene exothermically reacted with I and gave 2, 3-dihydro-9-methyl-3-oxo-2, 2-diphenyl-9H-imidazo[1, 2-a] benzimidazole (II).View full abstractDownload PDF (1028K) -
MASASHI TOMODA, MACHIKO TANAKA1973 Volume 21 Issue 5 Pages 989-994
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPlantasan, the seed mucilage of Plantago major L. var. asiatica DECAISNE, has been subjected to partial acid hydrolysis, and three disaccharides were obtained. Analysis of components, periodate oxidation, methylation and enzymic degradation studies provided the evidences that they are O-β-D-xylopyranosyl-(1→2)-D-xylopyranose, O-β-D-xylopyranosyl-(1→4)-D-xylopyranose, and O-β-D-glucopyranosyl-uronic acid-(1→5)-L-arabino-furanose.View full abstractDownload PDF (834K) -
MASANORI SONO, HIKOYA HAYATSU1973 Volume 21 Issue 5 Pages 995-1000
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs an extension of the work on the permanganate oxidation and the oxygen-mediated bisulfite reaction of 4-thiouridine, the reactions of 2-thiouracil were studied. On treatment with a stoichiometric amount of permanganate at pH 7 and 0°, 2-thiouracil yielded uracil-2-sulfonate. The sulfonate was susceptible to hydrolysis with weak acid but was stable in alkali. Kinetic studies of the acid hydrolysis were carried out. 2-Thiouridine also underwent a rapid oxidation on treatment with permanganate under similar conditions. Uridine and a small amount of uracil were detected as the products of the reaction of the nucleoside, suggesting that the intermediate uridine-2-sulfonate is more susceptible to hydrolysis compared with uracil-2-sulfonate. Treatment of 2-thiouracil with dilute bisulfite at pH 7 and room temperature under oxygen-bubbling resulted in quantitative formation of uracil-2-sulfonate. The mechanism of the reaction involves action of the free radicals generated during the autoxidation of bisulfite, a mechanism already had been described in the bisulfite reaction with 4-thiouridine.Oxygen-mediated bisulfite reaction with 2-thiouridine was shown to be complex, yielding not only uridine but also other products including an appreciable amount of uracil.View full abstractDownload PDF (820K) -
HIDEO IIDA, HONG-CHING HSU, TOYOHIKO KIKUCHI1973 Volume 21 Issue 5 Pages 1001-1004
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBischler-Napieralski reaction of phenolic bromo amide (VIII), which was obtained from the Schotten-Baumann reaction of 4-benzyloxy-2-bromo-5-hydroxyphenethylamine (VI) with 2-bromo-4, 5-dimethoxyphenylacetyl chloride (VII) and then reduction with NaBH4 of the resultant dihydroisoquinoline (IX) gave 7-benzyloxy-5-bromo-1-(2-bromo-4, 5-dimethoxybenzyl)-8-hydroxy-1, 2, 3, 4-tetrahydroisoquinoline(X). N-Methylation of X afforded XI. The Ullmann reaction of XI in the presence of potassium carbonate and cupric oxide in pyridine gave 6-benzyloxy-4-brome-1-methyl-9, 10-dimethoxy-1, 2, 3, 12, 12a-pentahydrobenzoxepino[2, 3, 4-i, j]isoquinoline (XII). Subsequent debenzylation and debromination of XII with hydrogen over 10% palladium-charcol gave dl-cularidine (Id) which was identified with natural cularidine by infrared and nuclear magnetic resonance spectral comparisons.View full abstractDownload PDF (535K) -
NORIYASU HIROSE, SHIZUO KURIYAMA, SHIGERU SOHDA, KENYA SAKAGUCHI, HIRO ...1973 Volume 21 Issue 5 Pages 1005-1013
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of 1- or 3-substituted spiro[cycloalkane-1', 2(1H)quinazolin]4(3H)-ones and the related compounds were synthesized for pharmacological testing. They could be prepared via anthranilic acid N-substituted amides or N-substituted anthranilamides with appropriate ketones, but attempts for introduction of the substituents at 1 or 3 position of spiro[cyclohexane-1', 2(1H)quinazolin]-4(3H)-one were failed. Mass fragmentation pathways are described for the several representative compounds briefly.View full abstractDownload PDF (1041K) -
YOSHIHIRO NISHIKAWA, KAZUHIKO MICHISHITA, GOICHI KURONO1973 Volume 21 Issue 5 Pages 1014-1019
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe low molecular weight carbohydrate constituents of eight species of lichens (Cetraria islandica, Cladonia crispata, C. rangiferina, C. squamosa, Peltigera aphthosa, P. nigripunctata, Umbilicaria caroliniana, and Usnea rubescens) have been analysed as their acetyl, trifluoroacetyl, and trimethylsilyl derivatives by gas chromatography. Glycerol, erythritol, ribitol, arabinitol, mannitol, fructose, glucose, sucrose, and trehalose were detected commonly in these lichens. In addition, the occurrence of 3-O-β-D-glucopyranosyl-D-mannitol in P. aphthosa and P. nigripunctata and of 2-O-β-D-galactofuranosyl-D-arabinitol (umbilicin) in C. islandica and U. caroliniana have been found.View full abstractDownload PDF (840K) -
GENICHIRO NONAKA, YOSHIKO KODERA, ITSUO NISHIOKA1973 Volume 21 Issue 5 Pages 1020-1026
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structure (I) of a new alkaloid, corydalic acid methyl ester, mp 140-141°, [α]D+85.4°, C22H23O6N, isolated from Corydalis incisa PERS. (Papaveraceae) only in the vegetative stage, was established by the spectroscopic studies and chemical correlation with mesotetrahydrocorysamine. Furthermore, on the basis of the stereochemical investigation of mesotetrahydrocorysamine, the stereostructure of corydalic acid methyl ester was determined as XII. Corydalic acid methyl ester is a noteworthy natural alkaloid in which aromatic ring is attached to the position-3 of the tetrahydroisoquinoline, and biogenetically it is supposed to be derived from protoberberine skeleton by a fission of B-ring, possibly through an aldehyde-type intermediate.View full abstractDownload PDF (828K) -
KIKUO ISHIZUMI, KAZUO MORI, SHIGEHO INABA, HISAO YAMAMOTO1973 Volume 21 Issue 5 Pages 1027-1030
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSChromic acid oxidation of N-phthalimidoacetylindoles (4) caused cleavage of the indole 2, 3-double bond affording the expected 2'-benzoyl-2-phthalimidoacetanilides (5). Ozonolysis, on the other hand, resulted in the formation and isolation of the stable crystalline ozonides (6). Ozonides (6) as well as 5 were shown to be converted into benzodiazepin-2-one (7) by treatment with hydrazine hydrate.View full abstractDownload PDF (615K) -
KAZUTAKE SHIMADA, YOUICHI FUJII, TOSHIO NAMBARA1973 Volume 21 Issue 5 Pages 1031-1036
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to obtain the more potent cardiotonic drug digitoxigenin 3-suberoylpeptides whose peptide moieties are derived from the partial structure of kinin, have been synthesized. Some of the desired compounds were prepared from digitoxigenin 3-suberoyl-p-nitrophenol (I) by direct condensation with the pertinent di- or tri-peptide. As for the steroidal peptides having the readily unavailable amino acid sequence the stepwise method involving the repeated p-nitrophenyl ester formation was carried out. The condensation reaction of p-nitrophenyl ester with amino acid or peptide was considerably improved in respect with the yield, when the amino group was activated by leading to the carbamate.View full abstractDownload PDF (853K) -
KAZUHIDE KAMIYA, YOSHIKAZU WADA, HIROAKI NOMURA, MASAO NISHIKAWA, SHIR ...1973 Volume 21 Issue 5 Pages 1037-1041
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe absolute configuration of (-)-α-sulfophenylacetic acid (II), the side chain acid of a novel antipseudomonal semisynthetic penicillin, (-)-α-sulfobenzylpenicillin (I), has been determined and confirmed to be in the D-series. Accordingly, the biologically more active diastereoisomer which is derived from II has been assigned to be D(-)-α-sulfobenzylpenicillin.View full abstractDownload PDF (596K) -
EUGENE L. PARROTT, ROBERT J. BRAUN1973 Volume 21 Issue 5 Pages 1042-1046
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSUsing micellar diffusion coefficients calculated by means of dissolution-rate and solubility measurements, the Stokes-Einstein equation was employed to estimate the relative micelle size and the micellar weight of benzoic acid-micelle species in solutions of polysorbate 80. The necessity of considering the relative viscosity of the micellar solutions and the variance of diffusion coefficients with concentration was demonstrated. Under the experimental conditions described it does not seem justifiable to use the Stokes-Einstein equation in the determination of micellar weight and/or size.View full abstractDownload PDF (583K) -
TETSUZO KATO, YUTAKA YAMAMOTO, SHIR0 TAKEDA1973 Volume 21 Issue 5 Pages 1047-1052
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of diketene with ketene acetals (Ia-f) has been studied on cycloaddition reaction to form 4-pyrone derivatives (II and III). Cyanoketene diethylacetal reacted with diketene to give 3-cyano-4-ethoxy-6-methy1-2-pyrone besides the formation of IIIf. IIa, b and IIIa, b, c, d, f were converted in good yields to corresponding 2-ethoxy-6-methyl-3-substituted-4-pyridone (V), respectively, whereas VI was converted to VIII and IX by treatment with ammonia.View full abstractDownload PDF (698K) -
SHUNSAKU SHIOTANI, TADASHI KOMETANI1973 Volume 21 Issue 5 Pages 1053-1060
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNew synthetic routes of 3-methyl-2, 3, 4, 5, 6, 7-hexahydro-2, 7-methano-1H-3-benzazonine (A) and 4-methyl-2, 3, 4, 5, 6, 7-hexahydro-1, 6-methano-1H-4-benzazonine (B) were described. A Schmidt reaction of ethyl 2-oxo-5-phenylcyclohexanecarboxylate (I) gave the corresponding lactam (II), which in turn was reduced with lithium aluminum hydride to afford 2-hydroxymethyl-4-phenyl-2, 3, 4, 5, 6, 7-hexahydro-1H-azepioe (III). The N-ben-zoyl derivative (IV) of III was oxidized with dimethylsulfoxide and dicyclohexylcar-bodiimide to give the corresponding aldehyde (V), which was submitted to oxidation with silver hydrodde to give N-benzoyl-4-phenyl-2, 3, 4, 5, 6, 7-hexahydro-1H-azepine-2-carboxylic acid (VI). Cyclization of VI by heating with polyphosphoric acid yielded 2, 3, -4, 5-tetrahydro-2, 7-methano-1H-3-benzazonin-7(6H)-one (VII). A Wolff-Kishner reduction and the successive N-methylation gave the final compound A. While, Wolff-Kishner reduction of the N-methyl derivative (IX) of VII gave an elimination product, 1-(N-methylaminopropyl)-1, 2-dihydronaphthalene (XI) . Treatment of 4-(N, N-dimethylaminoethyl)-3, 4-dihydronaphthalen-1(2H)-one (XII) with ethyl chlorocarbonate afforded a carbamate, 4-(N-methyl-N-ethoaycarbonylaminoethyl)-3, 4-dihydro-naphthalen-1(2H)-one (XIII), which was hydrolized, followed by a Mannich reaction with formaldehyde to yield 4-methyl-2, 3, 4, 5-tetrahydro-1, 6-methano-1H-4-benzazonin-7(6H)-one (XV). Reduction of the ketone XV with lithium aluminum hydride or by catalytic hydrogenation over Adams' catalyst gave the corresponding hydroxyl derivative (XVI), which was reduced with hydriodic acid and red phosphorus to give the final compound B.View full abstractDownload PDF (1044K) -
TAKASHI HARAYAMA, MITSUAKI OHTANI, MASAHARU OKI, YASUO INUBUSHI1973 Volume 21 Issue 5 Pages 1061-1068
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn connection with the synthesis of serratinine (A), the selective cyclization reaction of the 1, 2-cyclohexanediacetaldehyde derivatives, IIIa and IITb, through the intramolecular aldol condensation reaction was investigated. Cyclization reaction of IIIa or IITb by basic alumina or by the enamine method2) using piperidine acetate in dry benzene gave selectively IVa or IVb. On the other hand, cyclization reaction of IIIa or IIIb using excess pyrrolidine acetate in abs. MeOH afforded selectively Va or Vb which is suitable for the present purpose.View full abstractDownload PDF (1106K) -
MASARU KOBAYASHI, HIROSHI MITSUHASHI1973 Volume 21 Issue 5 Pages 1069-1075
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of nitrous acid with steroidal amides (I, VII, IX and X), α, β-unsturated ε-lactams (XIX and XXI), and enamine-type lactams (XXIV, XXVIII, XXX and XXXI) was studied. The amides mainly gave esters in low or modest yield with retention of the configuration. The α, β-unsaturated lactams gave N-nitroso-lactams quantitatively. The enamine-type δ-lactams gave oximino-δ-lactams in a high yield.View full abstractDownload PDF (1097K) -
JUN'ICHI HASE, KYOICHI KOBASHI, REIKO KOBAYASHI1973 Volume 21 Issue 5 Pages 1076-1079
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSInvestigations were performed on the correlation between the inhibitory power on Na+, K+-ATPase activity of phlorizin, asebotin, coreopsin, naringin-and hesperidin-chalcone and their chemical structure. Both chalcone and dihydrochalcone inhibited Na+, K+-ATPase activity, depending upon the number and position of phenolic hydroxyl group in their carbon skeleton. Free hydroxyl group at 4' position of phlorizin played an important role in the inhibitory power.View full abstractDownload PDF (524K) -
HIROAKI YANAGISAWA, HIDEO NAKAO, AKIKO ANDO1973 Volume 21 Issue 5 Pages 1080-1089
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSulfonamide or phosphonic acid analogs of oxolinic acid (I) and nalidixic acid (II), in which the carboxyl groups of I and II were replaced by sulfamoyl and phosphono groups, were synthesized conveniently by the modification of the Camps'es quinoline synthesis. They were evaluated for antimicrobial activity but no significant activity was noted.View full abstractDownload PDF (1259K) -
KOICHI HIRAI, HIDEBUMI MATSUDA, YUKICHI KISHIDA1973 Volume 21 Issue 5 Pages 1090-1095
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAttempts were made to prepare sulfur substituted 2-azetidinones by the reaction of vinylsulfide with chlorosulfonyl isocyanate (CSI). The main product of the reaction of β-methylthiostyrene (I) with CSI was pyridone derivative (II), but in the case of 1-phenylthio-1-propene (V) the main products were dihydrouracil derivatives (VI and VII) and acrylic acid derivatives (VIII and IX). Reaction of 1-p-chloro- or p-methylphenylthio-1-propene (Xa and b) with CSI in dry ether at -30°gave the desired 2-azetidinone (β-lactam) derivatives (XIa and b) in 63 and 66.4% isolated yield respectively.View full abstractDownload PDF (742K) -
NARAO TAKAO, HANS-WERNER BERSCH, SACHIKO TAKAO1973 Volume 21 Issue 5 Pages 1096-1102
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEs wird die Struktur des (+)-14-Epicorynolins, das provisorisch als Base II gezeichnet wurde, ein neues Alkaloid aus Corydalis incisa beschrieben. Das Des-N-Produkt (9) der Base II, das durch die aweimaligen Emde-Abbauen erhalten wurde, stimmt mit der optisch aktiven Form des Des-N-Produkts (7) des Corynolins uberein. Base II stimmt weder mit Corynolin (1) noch mit 11-Epicorynolin (3) uberein. Die aus Base II abgeleitete Anhydrobase (6) erwies sich als nicht identisch mit der optisch aktiven Anhydrobase (5) des Corynolins. Daher wurde festgestellt, dass die Verknupfungsweise der Ringe B und C in der Base II trans sein muss. (+)-14-Epicorynolin stellt den ersten Beispiel der Benzo(c)-phenanthridintyp-Alkaloide mit der trans-Verknupfung der Ringe B und C dar, die in der Natur vorkommen.View full abstractDownload PDF (1036K) -
YASUKO SUMI, FUJIO KAMETANI1973 Volume 21 Issue 5 Pages 1103-1107
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo of five isomers of 2, 3, 5, 6-tetramethyl-1, 4-dioxane were isolated. Their configurations were assigned with the coupling constants of the methine protons of the 1, 4-dioxane ring by nuclear magnetic resonance (NMR) spectrometry. 2, cis-3-Bis(Iodomethyl)-cis-5, trans-6-dimethyl-1, 4-dioxane (IIa) and 2, trans-3-bis-(iodomethyl)-trans-5, cis-6-dimethyl-1, 4-dioxane (IIb) were obtained by the cyclization reaction of meso- and dl-2, 3-butanediol, respectively, and 1, 3-butadiene with mercuric oxide and iodine. 2, cis-3, cis-5, trans-6-Tetramethyl-1, 4-dioxane (IIIa) and 2, trans-3, trans-5, cis-6-tetramethyl-1, 4-dioxane (IIIb) were obtained by reduction of IIa and IIb, respectively, with LiAlH4. The coupling constants and τ values of the methine protons of the 1, 4-dioxane ring were 3.3, 9.0 Hz, 6.16, 6.30, 6.54, 6.76 τ for IIIa, and 9.0 Hz, 6.77 τ for IIIb.View full abstractDownload PDF (561K) -
SANSEI NISHIBE, SUEO HISADA, ISAO INAGAKI1973 Volume 21 Issue 5 Pages 1108-1113
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new lignan glucoside named nortracheloside (IV), C26H32O12·H2O, mp 95-100°, was isolated from the stems of Trachelospermum asiaticum NAKAI var. intermedium NAKAI (Apocynaceae). The lignan derivatives were prepared from tracheloside (III) and nortracheloside (IV). From the discussion of mass spectra of the lignan derivatives, the structures of III and IV were established as 8(S), 8'(S)-4', 8'-dihydroxy-3, 4, 3'-trimethoxy-lignan-olid(9, 9')4'-β-D-glucopyranoside and 8(S), 8'(S)-4, 4', 8'-trihydroxy-3, 3'-dimethoxy-lignan-olid(9, 9')4'-β-D-glucopyranoside, respectively.View full abstractDownload PDF (767K) -
SANSEI NISHIBE, SUEO HISADA, ISAO INAGAKI1973 Volume 21 Issue 5 Pages 1114-1117
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new lignan diglucoside was isolated from the stems of Trachelospermum asiaticum NAKAI var. intermedium NAKAI (Apocynaceae) and its structure was established as nortrachelogenin-4, 4'-di-O-β-D-glucopyranoside (I). Also the presence of α-conidendrin glucoside was suggested.View full abstractDownload PDF (628K) -
YOSHIRO KOBAYASHI, ITSUMARO KUMADAKI, YASUO SEKINE, TERUO KUTSUMA1973 Volume 21 Issue 5 Pages 1118-1123
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe 1, 3-dipolar cycloaddition of dicyanoacetylene (IIb) to isoquinolinium ylides did not give the primary adduct but the aromatized and/or isomerized products. Further, in the reaction of isoquinolinium bis(methoxycarbonyl)methylide (Ia), possibly a rearranged addition product, 1, 10b-dihydropyrrolo[2, 1-α]isoquinoline (VII), was obtained beside 2, 3-dihydropyrrolo[2, 1-α]isoquinoline (Va) and pyrrolo[2, 1-α]isoquinoline (VIa). In the reaction of isoquinolinium cyano(methoxycarbonyl)methylide (Ib), 2, 3-dihydropyrrolo[2, 1-α]isoquinoline (VIII), formed by the liberation of a methoxycarbonyl group, was obtained in addition to VIa and pyrrolo[2, 1-α]isoquinoline-1, 2, 3-tricarbonitrile (VIb).View full abstractDownload PDF (758K) -
TETSUJI KAMETANI, EIKO TAGUCHI, KAZUYA YAMAKI, ATSUTO KOZUKA, TSUNEKAZ ...1973 Volume 21 Issue 5 Pages 1124-1126
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
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MITSURU FURUKAWA, YOKO KOJIMA, SEIGORO HAYASHI1973 Volume 21 Issue 5 Pages 1126-1131
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
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HIROSHI NAGASE1973 Volume 21 Issue 5 Pages 1132-1135
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
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SHIRO TERASHIMA, KATSUMI TAKASHIMA, TADAO SATO, SHUN-ICHI YAMADA1973 Volume 21 Issue 5 Pages 1135-1139
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
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YASUMITSU TAMURA, YOSHIO SUMIDA, SHIGEHARU TAMADA, MASAZUMI IKEDA1973 Volume 21 Issue 5 Pages 1139-1142
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
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AKIHIRO YAMAZAKI, MASAO AKIYAMA, IZUMI KUMASHIRO, MORIO IKEHARA1973 Volume 21 Issue 5 Pages 1143-1146
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
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TOKISHI HAYASHI, SATOSHI KAWAI, TAKEO OHNO1973 Volume 21 Issue 5 Pages 1147-1151
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
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KIYOMI KIKUGAWA, MOTONOBU ICHINO1973 Volume 21 Issue 5 Pages 1151-1155
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
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SANSEI NISHIBE, SUEO HISADA, ISAO INAGAKI1973 Volume 21 Issue 5 Pages 1155-1157
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
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YOSHIKAZU YAMATAKE, HITOSHI KATO, KEIJIRO TAKAGI1973 Volume 21 Issue 5 Pages 1157-1160
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
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SHUNSAKU SHIOTANI, TADASHI KOMETANI1973 Volume 21 Issue 5 Pages 1160-1163
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
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YASUHIRO FUJIWARA, SHOSHICHIRO KIMOTO, MASAO OKAMOTO1973 Volume 21 Issue 5 Pages 1166-1167
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
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HIDETOSHI YOSHIMURA, HIROAKI YAMAMOTO1973 Volume 21 Issue 5 Pages 1168-1169
Published: May 25, 1973
Released on J-STAGE: March 31, 2008
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