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Volume 21, Issue 6
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MASATAKE HORI, NORIO SUGITA, MITSUYO MIYAZAKI1973 Volume 21 Issue 6 Pages 1171-1174
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEnduracidin, a depsipeptide antibiotic, was separated into A and B by column chromatography. The amino acid compositions of A and B were found to be the same. This method also can be used for the quantitative separatory analysis of enduracidin A and B.View full abstractDownload PDF (446K) -
MASATAKE HORI, HIDESUKE IWASAKI, SATOSHI HORII, ISAMU YOSHIDA, TOSHIO ...1973 Volume 21 Issue 6 Pages 1175-1183
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe primary structure of enduracidin, a cyclodepsipeptide antibiotic, was estimated by the determination of the amino acid sequence, optical isomers of each amino acid, and lactone structure. The result is that the enduracidin has a macro-ring lactone structure which is composed of 16 amino acids, and has a side chain aspartic acid which is connected to a fatty acid by an amide bond. The tentative structure is shown in Fig. 7.View full abstractDownload PDF (879K) -
HIDESUKE IWASAKI, SATOSHI HORII, MITSUKO ASAI, KOMEI MIZUNO, JISABURO ...1973 Volume 21 Issue 6 Pages 1184-1191
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the structural investigation of acidic products obtained by hydrolysis of enduracidins and tetrahydroenduracidins, 10-methylundeca-2 (cis)-4 (trans)-dienoic acid (V) and (+)-10-methyldodeca-2 (cis)-4 (trans)-dienoic acid (VI) were found to be constituent of enduracidins A and B, respectively. Consequently, the structural difference between enduracidins A and B was proved to be present in their unsaturated fatty acid moieties, and their full structures were assumed to be as shown in Fig. 10.View full abstractDownload PDF (838K) -
KAZUAKI KYOGOKU, KATSUO HATAYAMA, SADAKAZU YOKOMORI, MASAHISA SHIO, MA ...1973 Volume 21 Issue 6 Pages 1192-1197
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new flavonoids were isolated from the root of Sophora subprostrata CHUN et T. CHEN, and their structures were established from their spectral data and comparison with the corresponding synthesized derivatives as 6-[3-(2', 4'-dihydroxyphenyl)acryloyl]-7-hydroxy-2, 2-dimethyl-8-(3-methyl-2-butenyl)-2H-benzopyran (I), 2-(2', 4'-dihydroxyphenyl)-8, 8-dimethyl-10-(3-methyl-2-butenyl)-8H-pyrano [2, 3-d] chroman-4-one (IV), and 2', 4', 7-trihydroxy-6, 8-bis (3-methyl-2-butenyl) flavanone (VIII).View full abstractDownload PDF (814K) -
KEN IKEDA, YUKIHISA KURONO1973 Volume 21 Issue 6 Pages 1198-1204
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVarious methanesulfonic acid derivatives of p, p'-diaminodiphenylsulfone (Da), which are represented as [chemical formula], were synthesized and their hydrolysis rates in vitro were investigated. The two methanesulfonic acid groups were hydrolyzed by steps in consecutive first-order reactions. The first hydrolysis rate was larger than the second rate in any of the derivatives. The electron-donating groups facilitate and the electron-withdrawing groups retard the hydrolysis. When R is HOCH2 (CHOH)4 (promin), phenyl, p-chlorophenyl, or p-nitrophenyl, the hydrolysis rate was pH-dependent and faster in the acidic region. The general acid catalysis by buffer constituents was studied in detail with promin. As a biopharmaceutical indication on the retardation of free Da liberation, kinetic induction period and the rate of accumulation in vitro were evaluated. Result from promin indicated that the liberation of parental Da in vivo is strikingly slow and a large part of therapeutic dose of promin, which is markedly larger than that of parental Da, may possibly be wasted in an ineffective form. The derivatives substituted with Me or Et have fast hydrolysis rate and these may be better in the avaliability of parenteral Da compared to promin.View full abstractDownload PDF (714K) -
MICHIYA KIMURA, KAZUAKI HARITA1973 Volume 21 Issue 6 Pages 1205-1212
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the 70% (w/w) HClO4 solution saturated with testosterone (I) at room temperature, colorless needles, of 1 : 1 complex (II) of I and HClO4 were isolated. When 0.2% (w/v) chloroform solution of I was heated with the equal volume of HClO4 under nitrogen stream for 30 min at 60-65°, the steric isomers (m/e=272) of 17-methyl-18-norandrost-4-en-3-one (III) were obtained from the organic layer. The deep-green acid layer gave the mixture of 17-methyl-18-norandrosta-4, 13 (17)-dien-3-one (IV) and 17-methyl-18-norandrosta-4, 13 (14)-dien-3-one (V). Standard specimens of IV and V gave easily the similar absorption spectra to that (Fig. 1) due to I, when they were dissolved in the dichloromethane solution saturated with HClO4. The dienones, IV and V, also gave the same spectra even in the moderately acidic conditions where I still remained inert. Partially hydrogenated product (III), on the contrary, failed to show any visible light absorption in the acid medium. It seems that the isomeric olefins, IV and V, are the intermediates in the present chromogenic reaction and the carbonium ions (VIII) formed by the protonation of them may play an essential part in producing the chromophore.View full abstractDownload PDF (956K) -
MINORU SEKIYA, TOSHIAKI MORIMOTO, KUNIO SUZUKI1973 Volume 21 Issue 6 Pages 1213-1217
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe aldol condensation products, 5-alkyl-4, 6-diacetyl-3-hydroxy-3-methylcyclohexanone (R=H, CH3, C6H5) and 3, 5-diacetyl-2, 6-heptanedione formed from 2, 4-pentanedione and aldehydes underwent further reactions involving aldol condensations and dehydrations on heating with the liquid formate, TEAF, given by 5HCO2H·2NEt3. These reactions finally gave the two isomers of dimethylbicyclo [3.3.1] nonadienediones. In the case of the formaldehyde condensation products, formate reactions giving 4, 6-diacetyl-3-methylcyclohex-2-en-1-one and 2, 4-diacetyl-5-methylphenol were also realized.View full abstractDownload PDF (711K) -
ISAO MATSUNAGA, ZENZO TAMURA1973 Volume 21 Issue 6 Pages 1218-1227
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS3-O-β-D-Glucopyranosiduronyl-D-glucaro-1, 4-lactone (VI), a new masked inhibitor of β-glucuronidase, was synthesized by the fusion of dimethyl 2, 4-O-benzylidene-5-O-acetyl-D-glucarate (I) and methyl 1-bromo-1-deoxy-2, 3, 4-tri-O-acetyl-α-D-glucopyranuronate (II) in the presence of mercuric cyanide, followed by removal of the protecting groups and lactonization. The chemical structure of VI was confirmed to be 3-O-β-D-glucopyranosiduronyl-D-glucaro-1, 4-lactone from the chemical and physical data of the products (III, IV, V, and VI) obtained in the course of its synthesis. The inhibitory effect of VI on β-glucuronidase in vitro was also examined.View full abstractDownload PDF (1069K) -
KATSUTOSHI KAMEI, ATSUSHI MOMOSE1973 Volume 21 Issue 6 Pages 1228-1234
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSGas chromatography and mass spectrometry are described for the analysis of methylated xanthines and their derivatives. A satisfactory separation of these compounds was achieved using 2% OV-17 and 3% XE-60 columns. Molecular ions of the methylated xanthines were observed as abundant peaks, and the trifluoroacetyl derivatives especially appear with base peaks. The fragmentation mechanisms were discussed.View full abstractDownload PDF (698K) -
MICHIYA KIMURA, KAZUAKI HARITA1973 Volume 21 Issue 6 Pages 1235-1239
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWhen epitestosterone (17α-hydroxyandrost-4-en-3-one) (I) was heated with formic acid, 17-methyl-18-norandrosta-4, 13 (17)-dien-3-one (III) and 17-methyl-18-norandrosta-4, 13 (14)-dien-3-one (IV) were formed, besides the 17α-formate of I. Kagi-Miescher reaction of I, III, and IV gave almost identical absorption spectra (Fig. 3). The olefinic products, III and IV, were, contrary to the original substrate (I), so sensitive that the bathochromic absorption was noticeable already at the first stage of this reaction without any heating. Although any increase in intensity was never observed on boiling in this case, a remarkable hyperchromic change at the wave-length (580 nm) of the maximum absorption was noticed at the second stage of the reaction, in which bromine molecules are the regular additive. It seems in the Kagi-Miescher chromogenic reaction that the possible intermediates, III and IV, including their protonated carbonium ions are oxidized mainly by bromine molecule to produce the characteristic chromophore in an acid medium.View full abstractDownload PDF (677K) -
TOSHIHIRO NOHARA, HIROKO YABUTA, MICHIHIRO SUENOBU, REIKO HIDA, KAZUMO ...1973 Volume 21 Issue 6 Pages 1240-1247
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSteroid glycosides in dried rhizomes of Paris polyphylla SM. obtained in a market of Katmandu, Nepal, were investigated. Diosgenin 3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-arabinofuranosyl-(1→4)]-β-D-glucopyranoside (I), mp 276-278°(decomp.), [α] D-133.0°, diosgenin 3-O-α-L-rhamnopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (V), mp 203-206°(decomp.), [α] D-153.2°, and pregna-5, 16-dien-3β-ol-20-one 3-O-β-chacotrioside (IX), mp 260-262°(decomp.), [α] D-72.2°, together with dioscin (diosgenin 3-O-β-chacotrioside) (VII), were isolated and characterized. I is the first diosgenin glycoside to have a L-arabinose unit and that in the furanose type, and V is a new tetraglycoside which could be regarded as a probable parent saponin of co-existing VII. IX attracts a particular attention in that the sugar moiety and the aglycone are respectively identical with and closely related to those of VII. Co-occurrence of the proto-type compounds of I and VII was also suggested.View full abstractDownload PDF (956K) -
YOSHIO ARATA, YOSHINOBU NAKAGAWA1973 Volume 21 Issue 6 Pages 1248-1253
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOctahydropyrido [1, 2-a] pyrazine (VI) and its N-benzyl derivative (I) were subjected to oxidation by mercuric acetate to afford 1, 3, 4, 6, 7, 8-hexahydro-2H-pyrido [1, 2-a] pyrazin-1-one (VII) and its N-benzyl compound (II), respectively. The former product (VII) was also obtained by similar oxidation of the lactam (V). Compound (V) was treated with methyl iodide in methanol to give two isomeric methiodides, trans-octahydropyrido [1, 2-a]-pyrazin-1-one methiodide (Xa) and the corresponding cis-methiodide (Xb). On thermal treatment, the latter methiodide was converted into the former. Methiodides, IV, XI, Xa, and Xb were reduced with lithium-liquid ammonia giving the 10-membered ring lactam (XII) in 4%, 52%, 81%, and 82% yields, respectively. When treated with sodium amalgam, Xa gave XII in 59% yield, which, on reduction with lithium aluminum hydride, yielded XIII.View full abstractDownload PDF (787K) -
HIKARU OKABE, KIYOSHI MATSUO, ITSUO NISHIOKA1973 Volume 21 Issue 6 Pages 1254-1260
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAlong with chrysophanol glucoside (I), mp 245-246°, C21H20O9·1/2H2O, and 8-O-β-D-glucopyranosides of physcion, emodin, aloe-emodin and rhein, three new anthraquinone glucosides, II : mp 187-189°, C21H20O10·2H2O, III : mp 239-241°, C21H20O10·1/2H2O and IV : mp 210-215°were isolated from the rhubarb, and II and III were respectively identified with 1, 8-dihydroxy-3 [-O-β-D-glucopyranosylmethyl]-aloe-emodin and 1-O-β-D-glucopyranosyl-emodin by spectral analyses of them, their permethylates and aglycones of permethylates. Although physical constants of I were quite the same with those of chrysophanein (1-O-β-D-glucopyranosyl-chrysophanol), I was found to be a mixture of 1-and 8-O-β-D-glucopyranosyl-chrysophanols by nuclear magnetic resonance spectral analysis of the aglycone of its permethylate.View full abstractDownload PDF (801K) -
MICHIYA KIMURA, KAZUAKI HARITA1973 Volume 21 Issue 6 Pages 1261-1266
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSpectroscopic and gas-chromatographic observations were done on the chromogenic reactions of testosterone (I) with Brφnsted acids such as sulphuric acid, phosphoric acid, and perchloric acid and with Lewis acids such as SbCl3, SbCl5, ZnCl2, and AlCl3. Although the spectra due to the reactions with various Brφnsted acids were different in each of the colorimetric procedures for I, the residues obtained from the reaction mixtures gave a similar spectrum with each other, when they were submitted again to the colour development at room temperature in the dichloromethane solution saturated with 70% HClO4 (Fig. 1). From this and the results of gas chromatography (Fig. 2) of these residues, 17-methyl-18-norandrosta-4, 13 (17)-dien-3-one (II) and/or 17-methyl-18-norandrosta-4, -13 (14)-dien-3-one (III) were/was likely to be the intermediary chromogen (s) commonly present in these colorimetric reaction mixtures. Lewis acids in the reactions with I, on the contrary, gave entirely different results as shown in Fig. 2 and 3. In contrast to I, the dienones, II and III, showed readily at room temperature the bathochromic absorption with HClO4 as well as SbCl5 in dichloromethane, which was markedly intensified in the presence of oxidizing agent (Fig. 4).View full abstractDownload PDF (807K) -
YUKO NAKAHARA, TAKASHI TATSUNO1973 Volume 21 Issue 6 Pages 1267-1271
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS12, 13-Epoxytrichothecenes could be determined quantitatively by gas chromatography after silylation of the sample with bistrimethylsilylacetamide (BSA). The method was applied to determine fusarenone X in fodder. The lower limit of detection of 12, 13-epoxytrichothecenes was 1μg/μl.View full abstractDownload PDF (540K) -
MIKIO HORI, TADASHI KATAOKA, KOSEI OHNO, TATSUO TOYODA1973 Volume 21 Issue 6 Pages 1272-1281
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOn nitration of 9-phenylxanthylium salt (I) with a mixed acid, 9-mononitrophenyl-xanthylium salt was obtained in 99% yield. The treatment of 9-phenylthioxanthylium salt (II) in the same condition gave a dinitrated product. Various nitration conditions were examined to obtain a mononitrated product. In order to determine the positions of the nitro group, various derivatives of I and II were synthesized. On the other hand, acetamido compounds derived from mononitrated I was separated into two isomers. It was thus proved that they were 9-(m-acetamidophenyl) xanthene (IVa) and 9-(p-acetamidophenyl) xanthene (IVb) in the ratio of 4.5 to 1.0, while mononitrated II gave 9-(m-acetamidophenyl) thioxanthene (XVa) and 9-(p-acetamidophenyl)-thioxanthene (XVb) in the ratio of 1.0 to 1.25. These results were particularly surprising in view of the fact that II was nitrated much easier than the oxygen analog I and also the p-nitro derivative was formed more than the m-nitro derivative.View full abstractDownload PDF (1131K) -
MIKIO HORI, TADASHI KATAOKA1973 Volume 21 Issue 6 Pages 1282-1286
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of 9-phenylthioxanthylium salt (II) with a mixed acid gave dinitrated II in 91% yield. In order to determine the structure of dinitrated II, 4-nitro-9-(m-nitrophenyl) thioxanthene (IV), 4-acetamido-9-(p-acetamidophenyl) thioxanthene (VI), 2, 4-dinitro-9-phenylthioxanthene (XV), and their ralated compounds were synthesized. And it was confirmed that the dinitration of II gives 4-nitro-9-(m-nitrophenyl) thioxanthylium and 4-nitro-9-(p-nitrophenyl) thioxanthylium salts in the ratio of formation being 1.0 : 1.2. Thus, it was recognized that the nitration of II occurs in the phenyl group at 9-position and then at 4-position in the hetero ring of II.View full abstractDownload PDF (629K) -
MASAYUKI ONDA, KEIJI TAKEUCHI1973 Volume 21 Issue 6 Pages 1287-1290
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn alumina-induced reaction of 6-acetoximino-3β-acetoxycholestan-5α-ol nitrite (I) is examined and affords several kinds of compounds. Among them II, III and IV are belong to the same type of compound. From the spectral data and their reactions, the structures containing 5α, 6α-epoxy and 6β, 7β-isonitrosoimino groups are tentatively assumed for them. V and VI are identified to be another type containing 5α-acetoxy and 6-oxo groups. The formation pathways of both types of compounds are deduced by comparison with the reaction products of the relative compounds.View full abstractDownload PDF (580K) -
KENSAKU KINOSHITA, TAKESHI FUJITA1973 Volume 21 Issue 6 Pages 1291-1294
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe metabolic fate of 57Co-hydroxocobalamin (57Co-OH-B12) and 57Co-5, 6-dimethyl-benzimidazolylcobamide coenzyme (57Co-DBCC) has been studied after intraperitoneal administration at the dosage of 25 μg/kg in rats. About 60% of radioactivity administered was recovered in urine during the first 24 hr after administration of 57Co-OH-B12 or 57Co-DBCC. The highest tissue uptake was found in kidney, especially after injection of 57Co-DBCC, followed by adrenal gland, pancreas, stomach and liver. The distribution in brain, muscle and adipose tissue was much lower. It is evident that 57Co-OH-B12 was converted to 57Co-DBCC and reverse conversion of 57Co-DBCC occured in liver and kidney. Furthermore, 57Co-methylcobalamin (57Co-CH3-B12) was found to be yielded from both the cobamides. The biological interconversion among 57Co-CH3-B12, 57Co-OH-B12and 57Co-DBCC was established.View full abstractDownload PDF (495K) -
TATSUYA ABE, AKIRA KAMBEGAWA1973 Volume 21 Issue 6 Pages 1295-1299
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFor the purpose of identifying a urinary metabolite of 17α-acetoxy-6-chloro-4, 6-pregnadiene-3, 20-dione (I, chlormadinone acetate) in the rabbit, 17α-acetoxy-6-chloro-2α, 3β-dihydroxy-4, 6-pregnadien-20-one (V), which was found to be identical with the metabolite, was synthesized from I. The starting material (I) was converted to the 2α-and 2β-acetoxy compounds (II and III) on heating with lead tetraacetate in acetic acid. When II and III were reduced with sodium borohydride in anhydrous isopropanol, two 2, 3-dihydroxy compounds (V and VI) were produced. These two diols were found to be 2α, 3β-diol (V) and 2β, 3β-diol (VI), It was also found that both diols formed acetonides. 17β-acetoxy-4-androstene-2α, 3β-diol (XIII) could be also transformed into the acetonide.View full abstractDownload PDF (645K) -
AKIRA TAKAMIZAWA, SAICHI MATSUMOTO1973 Volume 21 Issue 6 Pages 1300-1304
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBy the action of liquid ammonia, the cyclpadducts of isothiocyanates with 3, 4-dimethyl-5-(2-hydroxy) ethylthiazolium ylides (Ia-b) are converted into spiro [3, 3a-dimethylperhydrofuro [2, 3-d] thiazole-2, 4'-(5'-iminoimidazolidine)] derivatives (IIa-b), while the reactions of liquid ammonia with N-benzyl analogues (Ic-e) afford 3-aryl-6, 8-dimethyl-2, 9-dithia-4, 6, 8-triazatricyclo [3, 3, 0, 11, 5] oct-3-enes (IIIa-c) involving an unusual base-catalyzed cleavage reaction of the fused spiro thiazolidine ring. A possible mechanism of the novel transformation reaction is suggested.View full abstractDownload PDF (715K) -
KOICHI HIRAI, HIDEBUMI MATSUDA, YUKICHI KISHIDA1973 Volume 21 Issue 6 Pages 1305-1310
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReactivities of 3-methyl-4-arylthio-2-azetidinones (IIIa and IIIb) and their N-chlorosulfonyl derivatives (IIa and IIb) are discussed. Treatment of IIIa with hexamethylphosphoramide (HMPA) gave the acrylonitrile derivative (Va). The arylthio group of IIIa was easily oxidized with m-chloroperbenzoic aicd to afford the sulfoxide (VII), and further oxidation gave sulfone derivative (IX). Treatment of IIIa with iodine or bromine in methylene chloride gave the disulfide (VI) in high yield. Reaction of IIIa with 2-methylthio-2-thiazoline gave 6-methyl-5-oxo-5H-2, 3-dihydrothiazolo [3, 2-a] pyrimidine (XII) in 16% yield.View full abstractDownload PDF (683K) -
FUMITAKA TAKAMI, KANJI TOKUYAMA, SHIGERU WAKAHARA, TAKASHI MAEDA1973 Volume 21 Issue 6 Pages 1311-1317
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe decompositions of five N-monosubstituted dithiocarbamic acids (I) to isothiocyanate (V) and bisulfide ion were kinetically investigated over a wide range of alkali concentrations from pH to acidity function regions. The experimental first-order rate constants are proportional to the mole fraction of the anion form of I (II). The pH-rate profiles fit with an equation kobs=k [H+]/(KIII+[H+]) (eq. 4). The decomposition proceeds directly via II but not via III, conjugate base of II. The reaction was retarded by the reverse reaction of V with bisulfide ion. The effects of the initial concentration of I and bisulfide ion on the rate are also discussed.View full abstractDownload PDF (711K) -
MIKIO HORI, TADASHI KATAOKA, YUTAKA ASAHI, EIJI MIZUTA1973 Volume 21 Issue 6 Pages 1318-1326
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA close examination was made on the reactions between 9-phenylxanthylium salt (I) and various Grignard reagents, such as C6H5MgBr, o-and p-CH3OC5H4MgBr, and CH3MgI. It was found that the 9-phenylxanthyl radical (IX) is formed in these reactions as an intermediate ; from which 9-phenyl-9-substituted xanthenes are formed. 9-Phenylxanthenes V and VIII, which are derived from IX, are formed simultaneously. The electron spin resonance spectrum of the radical IX was analyzed by the McLachlan SCF-MO computation. Mechanism of the reaction of I with Grignard reagents were discussed in detail. The reaction between II and Grignard reagents gave the products similar to those of the reaction between I and Grignard reagents. It was confirmed that radical routes are related with the reaction mechanism to a considerable extent.View full abstractDownload PDF (886K) -
KAZUYOSHI IKEDA, TAKAHIKO SUMI, KUNIO YOKOI, YOSHIHISA MIZUNO1973 Volume 21 Issue 6 Pages 1327-1332
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDiazocoupling reaction of uracil derivatives bearing various substituents at position 5 was examined. The uracil derivatives having strong electron-releasing groups at this position were able to be coupled with a number of aryl diazonium salts to give the corresponding 6-arylazouracil derivatives. Catalytic reduction of 5-hydroxy-6-phenylazouridine (IX) prepared from 5-hydroxyuridine gave isouramil nucleoside (X). Stability of X in a pH-range (2.2-8.2) was examined and it was found that X was comparatively stable at pH ca. 3 in aqueous solution. The nucleoside having a new ring system, oxazolo (4, 5-d) pyrimidine nucleoside (XII) was prepared from X.View full abstractDownload PDF (764K) -
MASAYUKI ONDA, KUMIKO YUASA, JUNKO OKADA, KYOKO KATAOKA, KAORU ABE1973 Volume 21 Issue 6 Pages 1333-1337
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe methine base (X) derived from berberine chloride via several steps is photocyclized to the two isomeric carbinolamine forms (XI and XII) of 10b-methyl-4b, 10b, 11, 12-tetrahydrochelerythrine. Spectral data and chemical evidences reveal that the positions of the hydroxyl groups are C-6 in XI and C-4b in XII. The cis B/C ring juncture in XI is determined by observation of the nuclear Overhauser effect between 10b-Me and 4b-H. The formation pathways of XI and XII are examined and deduced to be the photoinduced intramolecular alkylation on carbon in the enamine system with olefin.View full abstractDownload PDF (666K) -
MIYUKI KANEDA, TAMOTSU SAITOH, YOICHI IITAKA, SHOJI SHIBATA1973 Volume 21 Issue 6 Pages 1338-1341
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new isoflavone, licoricone, C22H22O6, mp 250-251°, was isolated from the root of Glycyrrhiza uralensis FISCH, et DC. The chemical structure of licoricone was studied spectroscopically to lead a partial formula (VII). Finally an X-ray crystallographic analysis of its monobromoacetate (VIII) was undertaken to formulate licoricone as I.View full abstractDownload PDF (537K) -
SEIJU KUBOTA, MASAYUKI UDA1973 Volume 21 Issue 6 Pages 1342-1350
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOn the basis of ultraviolet (UV) and infrared (IR) evidence, 3-phenyl-1, 2, 4-triazolin-5-one and its N-methyl derivatives were all shown to exist as the oxo forms, except the 2-methyl derivative which existed as the hydroxy form. Similarly, UV data showed the predominance of the thione forms of 3-phenyl-1, 2, 4-triazoline-5-thione and its N-methyl derivatives. The syntheses of the N-methyl derivatives of the triazolines used in the present study were described.View full abstractDownload PDF (947K) -
SEIYU HIROSE, KAZUEI IGARASHI, KEIJIRO YAWATA, HISASHI FUKUZAWA, AKIRA ...1973 Volume 21 Issue 6 Pages 1351-1356
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn a comparison of the percutaneous absorption of 22Na+ with that of 36Cl-, zinc-EDTA-65Zn, ferric-EDTA-59Fe, ferric-tiron-59Fe or ferric-chromotropic acid-59Fe by the"double isotopic method, "it was demonstrated that water-soluble substances added simultaneously to absorption or hydrophilic ointment were absorbed at widely different rates through hair-clipped mouse skin. These results suggest that water-soluble substances added to an emulsion-type ointment may be absorbed through the skin into the body not as emulsified particles themselves but as solution or particles ultimately free of ointment base. It was also demonstrated that percutaneous absorbability of ferric-chromotropic acid-59Fe was significantly lower than that of ferric-tiron-59Fe when a comparison of the rates of absorption of these two radioactive compounds was made indirectly by using the absorption rate of 22Na+ added simutlaneously with each 59Fe-chelate compound to the absorption ointment as a standard. Thus, it was inferred that, when other conditions are similar, the percutaneous absorbability of water-soluble substances from emulsion-type ointment through mouse skin may be decreased with an increase in molecular size.View full abstractDownload PDF (772K) -
EIICHI FUJITA, TETSURO FUJITA, MANABU TAOKA, HAJIME KATAYAMA, MASAYUKI ...1973 Volume 21 Issue 6 Pages 1357-1363
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour diterpenoids were isolated from the dried leaves and stems of Isodon japonicus HARA. Two of them were shown to be identical with the known isodonal (2) and epinodosin (3). Spectroscopic investigation and a chemical conversion into epinodosin dihydroderivative (10) established the structure and absolute configuration of sodoponin as 11. The structure and absolute configuration of epinodosinol were elucidated as 16, on the basis of spectroscopic data and some chemical evidence. Finally, sodoponin (11) was converted into epinodosinol (16), which confirmed their structures unequivocally.View full abstractDownload PDF (699K) -
TADAKAZU TSUJI, MINAKO HARA1973 Volume 21 Issue 6 Pages 1375-1377
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
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TOHRU KIKUCHI, MINEO NIWA, TOSHIO YOKOI1973 Volume 21 Issue 6 Pages 1378-1380
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
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HARUAKI YAJIMA, FUSAKO TAMURA, YOSHIAKI KISO, MASAYUKI KUROBE1973 Volume 21 Issue 6 Pages 1380-1382
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
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MASAKO MURAOKA, TAKEO UEDA1973 Volume 21 Issue 6 Pages 1382-1385
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
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MASAICHIRO MASUI, KOHJI SUDA, MASASHIGE YAMAUCHI, NORIKO YOSHIDA1973 Volume 21 Issue 6 Pages 1387-1388
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
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TADASHI YASUHARA, MAYUMI HIRA, TERUMI NAKAJIMA, NOBORU YANAIHARA, CHIZ ...1973 Volume 21 Issue 6 Pages 1388-1391
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
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KOUICHIRO UMEMOTO1973 Volume 21 Issue 6 Pages 1391-1393
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
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GIICHI GOTO, KOUICHI YOSHIOKA, KENTARO HIRAGA, TAKUICHI MIKI1973 Volume 21 Issue 6 Pages 1393-1394
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
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JINSAKU SAKAKIBARA, KATSUSHIGE IKAI, MASAITI YASUE1973 Volume 21 Issue 6 Pages 1395-1396
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
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TOHRU KIKUCHI, TETSURO SHINGU, MINEO NIWA, TOSHIO YOKOI1973 Volume 21 Issue 6 Pages 1396-1397
Published: June 25, 1973
Released on J-STAGE: March 31, 2008
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