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KENJI KUMAKI, SUIICHI TOMIOKA, KYOICHI KOBASHI, JUNICHI HASE
1972 Volume 20 Issue 8 Pages
1599-1606
Published: August 25, 1972
Released on J-STAGE: March 31, 2008
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Regression analyses were made in the study of structure-activity relationship between hydroxamic acids and their inhibitory powers on urease activity according to the Hansch and Fujita's method. It was found that the primary effect of acyl residues in altering the inhibitory power of hydroxamic acid is associated with the hydrophobic character of the acyl residues. That is, the inhibitory power, pI
50, of the series of congeners such as n-aliphatic, m-substituted benzo-, and p-substituted benzohydroxamic acids vary parabolically with the hydrophobic parameter, π, of acyl residues and substituents. The optimal hydrophobic parameter, π
0, for acyl residue of n-aliphatic hydroxamic acid, which gives theoretically the strongest inhibitory power, was calculated to be 2.543. The results presented here suggest that hydrophobic character of acyl residue of hydroxamic acids plays two kinds of roles in urease inhibition ; the role in the random walk process of hydroxamic acids to the active site ; the other in the stereospecific hydrophobic bonding at the active site. On the other hand, electronic effect of acyl residues does not play a significant role in their inhibitory power on urease activity. Furthermore, it is assumed that in a series of araliphatic hydroxamic acids, the remarkable decrease in the inhibitory power of α-substituted derivatives is due to a steric effect of the bulky phenyl group in the α-position preventing the hydroxamic acid from proper fit on the active site of urease.
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KATSUHIKO OKUMURA, HITOSHI SEZAKI, KIICHIRO KAKEMI
1972 Volume 20 Issue 8 Pages
1607-1611
Published: August 25, 1972
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Absorption profiles of intramuscularly administered drugs, protonated at the physiological pH, and the fundamental problems concerning the specificity of their absorption were studied, using the rat thigh muscle clearance method and in vitro uptake experiments. 1) The intramuscular absorption rates of cationic drugs were lower than that of neutral or anionic drugs. 2) The absorption of cationic drug from the skeletal muscle was diminished as its concentration increased, and the absorption of isonicotinamide was depressed by the presence of cationic drugs. These results indicated that the vascular effect of cationic drug might influence the cationic drug absorption. 3) It was noted that cationic drugs were incorporated more rapidly than the other drugs into the muscle pieces suggesting the storage or affinity of these drugs to the muscle tissue. This was proposed as one of the factors influencing the low-absorptive nature of cationic drugs.
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AKIRA TAKAMIZAWA, YOSHIHIRO TOCHINO, YOSHIO HAMASHIMA, TSUYOSHI IWATA
1972 Volume 20 Issue 8 Pages
1612-1616
Published: August 25, 1972
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Two crystalline metabolites (2, 3) of cyclophosphamide (1) were isolated from rabbit urine. The structures of 2 and 3 were determined from their physicochemical data, and confirmed by synthesis. The positions of 2 and 3 in the metabolic pathway of 1 in living animals were discussed briefly.
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MITSUJI YANAI, TOSHIO KINOSHITA, SHIGEKO TAKEDA, MASAKUNI NISHIMURA, T ...
1972 Volume 20 Issue 8 Pages
1617-1620
Published: August 25, 1972
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The reaction product of 3-hydrazino-4-amino-6-chloropyridazine (IX) with formic acid was established to 6-chloro-8-amino-s-triazolo [4, 5-b] pyridazine (XII) by synthetic method and nuclear magnetic resonance spectral studies. 3-Benzylideneamino-6-chloroimidazo [4, 5-c] pyridazine (XI) was hydrolyzed to give 3-benzylidenehydrazino-4-amino-6-chloropyridazine (X), benzaldehyde and XII which was confirmed as a ring isomerization product of XI.
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KEN IKEDA, YUKIHISA KURONO, TYOTARO TUKAMOTO
1972 Volume 20 Issue 8 Pages
1621-1627
Published: August 25, 1972
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Successively reversible hydrolysis of methanesulfonic acid derivative of sulfisoxazole, R'NHSO
2C
6H
4NHCHRSO
3Na (R=CH
3 or C
6H
5), was studied. By the sequential hydrolysis such derivative may be hydrolyzed to the extent that the precipitation of parental drug may take place. The pH-profiles of logarithm of apparent hydrolysis and reverse reaction rates and those of equilibrium constants were obtained and the effect of ionizations of the derivatives and hydrolyzates have been explained by theoretical equations. From the hydrolysis and reverse reaction rates estimated, reaction pathway of individual reactions which compose whole hydrolysis system has been discussed.
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SHIGEHO INABA, KIKUO ISHIZUMI, TADASHI OKAMOTO, HISAO YAMAMOTO
1972 Volume 20 Issue 8 Pages
1628-1636
Published: August 25, 1972
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A new synthetic route for the preparation of 2, 3-dihydro-1H-1, 4-benzodiazepines (6) is described. It consists of performing successively N-cyanomethylation of ethyl indole-2-carboxylates (1), reduction of cyano group, oxidation of 1-aminoethylindole derivatives (3 or 4) and finally hydrolysis of 2, 3-piperazinediones (5). In an alternative synthesis of the key intermediate 4a, intramolecular alkylation of N-(2-chloroethyl) indole-2-carboxamide (11) gave a mixture of 4a and 2-oxazolinylindole (12).
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AKIRA TAHARA, YASUO OHTSUKA
1972 Volume 20 Issue 8 Pages
1637-1647
Published: August 25, 1972
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Dimethyl 1, 2, 3, 10-tetrahydro-4β, 10α-dimethyl-4H-fluorene-4α, 6-dicarboxylate and its hydrogenated stereoisomers were nitrated with conc. HNO
3-Ac
2O to give mononitro compound as a single product. Namely, ⊿
5-diester (X) was nitrated to give only 12-nitro compound (XI) and, in contrast, four possible stereoisomers due to the asymmetric centers at C-5 and C-6 of the saturated diester (XVII, XVIII, XIX, and XX) gave only 13-nitro compounds (XXI, XXII, XXIII, and XIV, respectively). Accordingly, 12-and 13-substituted (NO
2, NH
2, OH, and OMe) compound could be optionally obtained herein.
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AKIRA TAHARA, YASUO OHTSUKA
1972 Volume 20 Issue 8 Pages
1648-1655
Published: August 25, 1972
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Syntheses of 12- and 13-hydroxy diesters (XIII, XIV, XXI, and XXII) regarded as important intermediates for the formation of D-ring as in gibberellin, were accomplished in the unstable trans-(II) and stable cis-A/B-ring fused isomer (V) by reduction in lithium-liq. ammonia system and then by hydration with mercuric acetate. It is noticeable that 12-hydroxy diester (XX) obtained by epimerization at C-6 of the unstable form (XIII) has the same skeleton as in A- and B-ring of gibberallin A
12.
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TOSHIKIRO KIMURA, HITOSHI SEZAKI, KIICHIRO KAKEMI
1972 Volume 20 Issue 8 Pages
1656-1662
Published: August 25, 1972
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The site specificity in the absorption of sodium taurocholate (STC), one of the most common bile salts, and its consequence on drug absorption was investigated in the rat using the in situ perfusion technique. The absorption of STC by the jejunum was negligible both below and above the critical micellar concentration and it was absorbed solely by the ileum. Marked but variable change in absorbability of drugs was observed depending upon the physicochemical nature and the absorptive characteristics of drugs. The extent of the bile salt enhancement of the absorption of sulfaguanidine was more predominant in the ileum than in the jejunum, while the inhibitory effect of STC on the absorption of imipramine was less remarkable in the ileum. Possible mechanisms of these site specificity was discussed.
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HARUO SAIKACHI, NOBUHIRO SHIMOJO, YASUJIRO UEHARA
1972 Volume 20 Issue 8 Pages
1663-1668
Published: August 25, 1972
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It was found out that N-(2-furoyl)-N'-aryl aldehyde hydrazones (Schiff's base) were even more available as starting material for the formation of the corresponding 2-(2-furyl)-5-aryl-1, 3, 4-oxadiazole rings by the oxidative cyclization of lead tetraacetate.
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NORIYASU HIROSE, SHIGERU SOHDA, SHIZUO KURIYAMA, SHOJI TOYOSHIMA
1972 Volume 20 Issue 8 Pages
1669-1677
Published: August 25, 1972
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A total of 39 derivatives of 3-alkyl-1-[ω-(N-substituted amino)alkyl]-3-phenylindolin-2-ones and their related compounds were synthesized for pharmacological testing. Compounds were tested for analgetic-antiphlogistic activity by anti-writhing tests in mice. Acute toxicity and effects upon the general behaviour in mice were also determined.
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TETSUJI KAMETANI, TETSUYA KOHNO, KEIICHIRO FUKUMOTO
1972 Volume 20 Issue 8 Pages
1678-1680
Published: August 25, 1972
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The reductive rearrangement of the dienol (V), derrived from erythrinadienone (III), did not give the proposed dibenzazonine analog (IV), but V was converted to the dibenzazonine (VI) in methanolic hydrochloric acid solution. The catalytic hydrogenation of (III) has also been examined.
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TETSUYA NAKAMURA, SHIZUMASA KIJIMA
1972 Volume 20 Issue 8 Pages
1681-1686
Published: August 25, 1972
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Direct hydroxymethylation of β-(I) and γ-tocopherol (III) and their model compounds are established with boric acid catalyst. The yields of 7-hydroxymethyl-β-tocopherol (V), 5-hydroxymethyl-γ-tocopherol (VII), 6-hydroxy-7-hydroxymethyl-2, 2, 5, 8-tetramethylchroman (VI), and 6-hydroxy-5-hydroxymethyl-2, 2, 7, 8-tetramethylchroman (VIII) are 83%, 86%, 75%, and 78%, respectively. 5-Methyl-
14C-d-α-tocopheryl acetate (XIV) is synthesized by the procedure. 1, 1-Bis (β-tocopherol-7'-yl)-methane (XVII), 1, 1-bis (γ-tocopherol-5'-yl)-methane (XV), and their acetates (XVIII) and (XVI) are synthesized from corresponding hydroxymethyl tocopherols and tocopherols.
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TERUHIKO MESHI, SUSUMU NAKAMURA, YOSHISHIGE SATO
1972 Volume 20 Issue 8 Pages
1687-1698
Published: August 25, 1972
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The isolation and identification of urinary metabolites of PG-501, a new antiparkinsonian agent, has been investigated in rats. PG-501 was extensively metabolized by rat since only less than 0.1% of the drug was recovered unchanged in the 24 hour urine. A part of PG-501 was first N-demethylated and then hydrolyzed, and almost all of the remainder was directly hydrolyzed to granatane base and α, α-di (2-thienyl) glycolic acid (DTGA). A part of granatane base was further metabolized by glucuronic acid conjugation. Most of DTGA was further metabolized by dethienylation, decarboxylation, glucuronic acid conjugation and mercapturic acid conjugation. The major metabolites of granatane base were 6, 6, 9-trimethyl-3-hydroxygranatane, 6, 6-dimethyl-3-hydroxygranatane and their glucuronic acid conjugates whereas major metabolites of DTGA were glucuronic acid conjugate of DTGA, glucuronic acid conjugate of 2-thiophenecarboxylic acid, N-acetyl-S-[5-(2-thiophenecarbonyl)-2-thienyl]-L-cysteine, and 2-thiopheneglyoxylic acid. Studies of urinary metabolites of rats given N-
14CH
3-PG-501 showed that a part of formaldehyde produced by N-demethylation of the drug was excreted in urine as methionine, N-formylcysteine, N, N'-diformylcystine, formic acid and urea.
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MASUO MURAKAMI, NORIYOSHI INUKAI, NORIAKI NAGANO
1972 Volume 20 Issue 8 Pages
1699-1705
Published: August 25, 1972
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1, 3-Dihydroxy-5, 6, 7, 8-tetrahydroisoquinoline (VI) was synthesized from ethyl 2-ethoxycarbonyl-cyclohexylidene-cyanoacetate (IV) by treating it with concentrated sulfuric acid at 80-90° for five hours. 5, 6, 7, 8-Tetrahydroisoquinoline (VIII) was synthesized from VI by first chlorinating it to form 1, 3-dichloro-5, 6, 7, 8-tetrahydroisoquinoline (VII) and then reducing VII with zinc dust in acetic acid. The synthesis of 3-hydroxy-N-methylmorphinan (II) starting from VIII was carried out according to the methods reported by Grewe and Schnider, et al. with some modifications. Several new 3-substituted derivatives of N-methylmorphinan were synthesized from II. In these derivatives, d-N, N'-dimethyl-3, 3'-(carbonyldioxy)-dimorphinan (d-XVIII) synthesized from d-II and phosgene showed nearly the same antitussive activities as dextrometorphan (I) and a toxicity lower than the latter. Furthermore, d-XVIII did not form any physical dependence.
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MASUO MURAKAMI, SHIGEMI KAWAHARA, NORIYOSHI INUKAI, NORIAKI NAGANO, HI ...
1972 Volume 20 Issue 8 Pages
1706-1710
Published: August 25, 1972
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N-Methyl-5, 6, 7, 8-tetrahydroisoquinolinium bromide (IV) was reacted with p-methylbenzyl chloride by means of Grignard reaction to obtain 1-(4-methylbenzyl)-2-methyl-1, 2, 5, 6, 7, 8-hexahydroisoquinoline (V). V was immediately reduced to 1-(4-methylbenzyl)-2-methyl-1, 2, 3, 4, 5, 6, 7, 8-octahydroisoquinoline (VI) with sodium borohydride. VI was resolved by means of L(+)-tartaric acid. d, l and dl-VI were cyclized to d, l and dl-3-methyl-N-methylmorphinan (II), respectively, by treating them with 85% phosphoric acid at 135-150°. Several 3-methyl-N-alkyl and alkenyl-morphinan derivatives were synthesized from 3-methylmorphinan (VIII), which was prepared by demethylation of II, by treating it with alkyl and alkenyl halides. Antitussive activities of d-II were 1.5 times as strong as that of dextrometorphan (Ib), and a toxicity of d-II was lower than that of Ib. Furthermore, d-II did not form any physical dependence.
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KENTARO HIRAI, TERUYUKI ISHIBA, HIROHIKO SUGIMOTO
1972 Volume 20 Issue 8 Pages
1711-1715
Published: August 25, 1972
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1, 3-Dithiol-2-ylidene and 1, 3-oxathiol-2-ylidene derivatives were prepared by a simple method. 2-Immonio-1, 3-dithiole, 2-immonio-1, 3-oxathiole, and 2-immonio-1, 3-dithiolane were condensed with a variety of active methylene compounds giving the corresponding 2-ylidene derivatives readily. Some active methylene compounds, however, gave ketene S, N-acetals in the reaction with 2-immonio-1, 3-oxathiole.
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SHINSAKU MINAMI, MASATSUGU TOMITA, KAZUYO KAWAGUCHI
1972 Volume 20 Issue 8 Pages
1716-1728
Published: August 25, 1972
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In order to obtain useful antimicrobial compounds, a number of N-heterocyclic-β-mercaptocinnamamides (IIIa-i) and related compounds were prepared. N-Heterocyclic phenylpropiolamides (I) were obtained by the reaction of heterocyclic amines with phenylpropioloyl chloride. The addition of thiourea to I gave the isothiuronium salts (II), which were converted into the mercapto compounds (III) with aqueous sodium hydroxide. In the reaction of 2-aminothiazole or 2-amino-4-methylthiazole with phenylpropioloyl chloride in the presence of triethylamine, thiazolo [3, 2-α] pyrimidines (V, VII and VIII) were given together with the expected amides (If and Ig). The hydrolysis of S-[2-(3-methyl-1-phenyl-5-pyrazolyl) carbamoyl-1-phenylvinyl]-isothiourea p-toluenesulfonate (IIe) with aqueous sodium hydroxide at 90° gave 6, 7-dihydro-1, 4-diphenyl-3-methyl-6-oxopyrazolo [3, 4-b] pyridine (IX) and a small amount of the mercapto compound (IIIe). Acyl migration from S to N was found in the acylthio derivatives of N-(2-thiazolyl)-(IIIf) and N-(4-methyl-2-thiazolyl)-β-mercaptocinnamamide (IIIg). Most of the compounds synthesized were considerably active in vitro against various gram-positive bacteria and fungi. However, only three of them were effective against Trichophyton in the in vivo tests.
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AKIHIRO TADA, JUNZO SHOJI
1972 Volume 20 Issue 8 Pages
1729-1734
Published: August 25, 1972
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The chemical structure of ophiopogonin B, C
39H
62O
12·2H
2O, mp 269-271°, [α]
15D-105.5°(pyridine), a main glycoside isolated from the tuber of Ophiopogon japonicus KER-GAWLER var. genuinus MAXIM. (Liliaceae) was established to be ruscogenin (1)-α-L-rhamnopyranosyl (1
rham→2
fuc)-β-D-fucopyranoside as represented by formula (Ia). It should be noted that ophiopogonin B is one of the examples of the spirostane type glycosides whose sugar moiety links to the hydroxyl group other than C
3-hydroxyl group of the aglycone.
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TAKESHI OISHI, HIROSHI NAKAKIMURA, MIWAKO MORI, YOSHIO BAN
1972 Volume 20 Issue 8 Pages
1735-1739
Published: August 25, 1972
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The condensations of 1-methyl-2-piperidone diethylacetal (VI) and 1-methyl-2-pyrrolidone dimethylacetal (XX) with several electrophiles were carried out and it was found that VI afforded the 3, 3-disubstituted compounds. When benzyl chloride was used, even the compound VI afforded the 3-monosubstituted compounds. The mechanism for this anomaly is discussed.
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TAKESHI OISHI, SHINJI MURAKAMI, YOSHIO BAN
1972 Volume 20 Issue 8 Pages
1740-1744
Published: August 25, 1972
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The reaction of 1-methyl-2-pyrrolidone dimethylacetal (IV) with dimethyl acetylenedicarboxylate (I) was carried out expecting the formation of the simple dihydroazepine derivative. However, the products actually obtained were the indoline derivative (VI), the isomeric pyrrolidone derivatives (VII and VIII) and the tetracarbomethoxy-1, 3-butenyl pyrroline derivative (IX) when dioxane was used as the solvent, while the 1 : 1 adduct (X) was found to be the main product when the reaction was carried out in benzene. On the other hand, when 1-methyl-2-methylmercapto-2-pyrroline (XIII) was employed, the desired product (XIV) was obtained as a main product along with VI, VII, the Diels-Alder adduct (XV), and dimethyl 2, 3-bis-methylmercaptosuccinate (XVI).
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YOSHIO ARATA, MASAKATSU SAKAI, SHINGO YASUDA
1972 Volume 20 Issue 8 Pages
1745-1751
Published: August 25, 1972
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Monoester of benzylmalonic acid (I) and 3-carboxy-4-octahydroquinolizinone (V) were coupled with benzenediazonium salt to yield labile phenylhydrazones, Iia and VII, respectively. IIa was kept standing in chloroform or heated to give another phenylhydrazone (IIb). VIa was similarly converted into VIb. The condensed four-cyclic compound (VIIIa) derived from VIa or VIb was heated with hydrochloric acid and the resulting product (IXa) was subjected to Pictet-Spengler reaction by formalin to afford octahydroindolo [3, 2-b] quinolizine (Xa). Xa was also obtained by reduction of VIIIa with LAH. Treatment of IXa with benzaldehyde in aqueous hydrochloric acid produced XII. Some methoxyl derivatives (VIIIb, Xb) were obtained according to the same route as mentioned above.
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EIICHI FUJITA, MANABU TAOKA
1972 Volume 20 Issue 8 Pages
1752-1754
Published: August 25, 1972
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On the basis of chemical and spectroscopic evidence, the structure and absolute configuration of lasiokaurin and lasiodonin, which were isolated from Isodon lasiocarpus (HAYATA) KUDO, were established as ent-7β, 20-epoxy-1β-acetoxy-15-oxo-16-kaurene-6α, 7α, 14α-triol (II) and ent-7β, 20-epoxy-15-oxo-16-kaurene-1β, 6α, 7α, 11α-tetraol (VIII), respectively.
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AKIRA YAGI, YUKO WASHIDA, NAOE TAKATA, ITSUO NISHIOKA
1972 Volume 20 Issue 8 Pages
1755-1761
Published: August 25, 1972
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Phenolic components in the plant were investigated to give phyllodulcin, phyllodulcin-8-0-β-D-glucoside, hydrangenol, umbelliferone, p-hydroxybenzoic acid, protocatechuic acid, gallic acid, methyl chlorogenate, chlorogenic acid, kaempferol, quercetin, isoquercitrin, rutin and three new components, hydrangea glucosides A, B, and C. On the basis of chemical and spectral data hydrangea glucosides A (I), B (II), and C (III) were characterized to 2-[β-(4'-hydroxyphenyl)-β-hydroxyethyl]-6-hydroxybenzoic acid-6-0-β-D-glucopyranoside, 2-[β-(4'-hydroxyphenyl)-β-hydroxyethyl]-6-hydroxybenzoic acid-β-O-β-D-glucoside and p-hydroxybenzaldehyde-O-β-D-glucopyranoside, respectively.
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KEIICHI ITO, MINORU SEKIYA
1972 Volume 20 Issue 8 Pages
1762-1767
Published: August 25, 1972
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For the present investigation on catalytic hydrogenation the compounds in which both amide nitrogen and ether oxygen are bound to the same carbon were provided as several cyclic compounds such as tetrahydro-4H-1, 3-oxazin-4-ones and 4-oxazolidinones, the former being newly prepared in the present work. Our objective was to know the condition of possible hydrogenolysis, which may proceed at either one of the two carbon bonds. The hydrogenolyses proceeded in acetic acid solvent over palladium-on-charcoal catalyst under high hydrogen pressure and, from the results of product analyses, were shown to be selectively effected at the carbon-oxygen bond of the compounds.
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ZENICHI HORII, TAKESHI IMANISHI, TETSUAKI TANAKA, IKUKO MORI, MIYOJI H ...
1972 Volume 20 Issue 8 Pages
1768-1773
Published: August 25, 1972
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The catalytic hydrogenation of 6-(4-Methoxy-2-pyridyl)-1, 4-dioxaspiro [4, 5] decan-6-ol (V) gave VIa as a major product and VIb as a minor product. Their stereochemistries were determined by the nuclear magnetic resonance spectra of their oxathiazolidine derivatives (XIIIa and XIIIb, respectively).
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ZENICHI HORII, TAKESHI IMANISHI, MIYOJI HANAOKA, CHUZO IWATA
1972 Volume 20 Issue 8 Pages
1774-1777
Published: August 25, 1972
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10a-Episecuritinine (II), a diastereoisomer of securitinine (III), was synthesized from 2-hydroxy-2-(4-methoxy-2-piperidyl) cyclohexanone (I) whose stereochemistry was already determined.
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TSUKINAKA YAMANA, YUZO MIZUKAMI, AKIRA TSUJI, MASAHIRO IKUTA
1972 Volume 20 Issue 8 Pages
1778-1784
Published: August 25, 1972
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Attempt was made to determine the number of water molecules needed from ground state to transition state in acid-catalyzed hydrolysis of amide. Using relative first-order rate constants and ionization ratios for derivative and standard amide could lead to the medium independence of activity coefficient term in the rate expression of amide acidic hydrolysis. Good linear relationship in the derivation of the relative hydration number (γ'-γ) between derivative (γ') and standard amide (γ) was obtained for the various amide hydrolyses in perchloric acid solutions. The observed (γ'-γ)-values were consistent with the mechanism change and with change in reactivity.
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TOYOZO TAKADA, MITSUO AKIBA
1972 Volume 20 Issue 8 Pages
1785-1792
Published: August 25, 1972
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The compound related to mitomycin B, 2, 3-dihydro-7-hydroxy-6, 9-dimethyl-5, 8-dioxo-1H-pyrrolo [1, 2-α] indole (III), was synthesized starting from 2, 3, 9, 9a-tetrahydro-6, 9-dimethyl-7-nitro-1H-pyrrolo [1, 2-α] indole (II) via 2, 3-dihydro-6, 9-dimethyl-7-nitro-1H-pyrrolo [1, 2-α] indole (X), 7-amino-2, 3-dihydro-6, 9-dimethyl-1H-pyrrolo [1, 2-α] indole (XI), and 2, 3-dihydro-6, 9-dimethyl-7, 8-dioxo-1H-pyrrolo [1, 2-α] indole (VII). Some considerations were made on the mechanism of the formation of the dimers, 2, 3-dihydro-5-(2', 3', 9', 9a'-tetrahydro-6', 9'-dimethyl-1H-pyrrolo [1, 2-α] indol-7'-imino)-6, 9-dimethyl-7, 8-dioxo-1H-pyrrolo [1, 2-α] indole (VIII) and 2, 3-dihydro-5-(2', 3'-dihydro-6', 9'-dimethyl-1H-pyrrolo [1, 2-α] indol-7'-imino)-6, 9-dimethyl-7, 8-dioxo-1H-pyrrolo [1, 2-α] indole (IX), obtained by the oxidation of 7-amino-2, 3, 9, 9a-tetrahydro-6, 9-dimethyl-1H-pyrrolo [1, 2-α] indole (V) with Fremy's salt.
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TETSUJI KAMETANI, KEIICHI TAKAHASHI, TOSHIO HONDA, MASATAKA IHARA, KEI ...
1972 Volume 20 Issue 8 Pages
1793-1799
Published: August 25, 1972
Released on J-STAGE: March 31, 2008
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Photolysis of the 1-(2-bromobenzyl)-1, 2, 3, 4-tetrahydro-7-hydroxyisoquinolines (VII, VIII, and X) gave the proerythrinadienones (XIII, XIV, and XV), which would be key precursors for several isoquinoline alkaloids. The acidic treatment of these dienones and the corresponding dienols (XXXII) was investigated under several conditions.
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TETSUJI KAMETANI, KEIICHIRO FUKUMOTO, MICHIO FUJIHARA
1972 Volume 20 Issue 8 Pages
1800-1804
Published: August 25, 1972
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5, 5a, 6, 7, 8-Pentahydro-1-hydroxy-2, 11-dimethoxybenzo [b] oxepino [7, 6, 5-ij] isoquinoline (III) was synthesized by an intramolecular Ullmann reaction of 1-(3-benzyloxy-2-bromo-4-methoxybenzyl)-5-bromo-1, 2, 3, 4-tetrahydro-8-hydroxy-7-methoxy-2-methylisoquinoline (X), followed by hydrogenolysis of the product (XI), and also by reduction of N-ethoxycarbonyl analogue (XV) derived from Ullmann reaction product (XIV) of the phenolic bromoisoquinoline (XIII).
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HIDEHIKO HAGA, TOSHIO IMANARI, ZENZO TAMURA, ATSUSHI MOMOSE
1972 Volume 20 Issue 8 Pages
1805-1808
Published: August 25, 1972
Released on J-STAGE: March 31, 2008
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A gas chromatographic method and GC-MS is described for the analysis of urinary sugar alcohols as their trifluoroacetyl derivatives. Nine urinary sugar alcohols were identified ; erythritol, threitol, fucitol, ribitol, arabinitol, xylitol, mannitol, glucitol and galactitol. The occurrence of fucitol in urine is noteworthy.
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TERUO KUTSUMA, KAZUO FUJIYAMA, YOSHIRO KOBAYASHI
1972 Volume 20 Issue 8 Pages
1809-1814
Published: August 25, 1972
Released on J-STAGE: March 31, 2008
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1, 3-Dipolar cycloaddition of isoquinolinium cyano (methoxycarbonyl) methylide (V) and dimethyl acetylenedicarboxylate gave only one (VI) of the two possible primary adducts. Examination of the pyrolysis of this adduct revealed the structure of VI to have 10bhydrogen and 3-ester group in cis configuration. Heating of VI afforded 2, 3-dihydropyrroloisoquinoline (VIII), while its treatment with hydrogen chloride in benzene, followed by neutralization with potassium carbonate afforded the adduct (XIII) of two diastereoisomers (VIII and XIV). VIII was found to be unstable to acid and base, resulting in immediate hydrolysis of the ester group in its 3-position and decarboxylation to the diester (X). From the consideration of its reaction mechanism, the ester group in the 2- and 3-positions of VIII was determined to have a cis configuration and those in XIV, a trans configuration.
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FUMIO YONEDA, KATSUNORI MERA
1972 Volume 20 Issue 8 Pages
1815-1818
Published: August 25, 1972
Released on J-STAGE: March 31, 2008
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TOZO FUJII, TAISUKE ITAYA, SATOSHI MORO
1972 Volume 20 Issue 8 Pages
1818-1821
Published: August 25, 1972
Released on J-STAGE: March 31, 2008
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HIROMI TERAUCHI, TAEKO IRINO, SHOJI TAKEMURA
1972 Volume 20 Issue 8 Pages
1821-1823
Published: August 25, 1972
Released on J-STAGE: March 31, 2008
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MITSURU FURUKAWA, KENJI NAGATO, YOKO KOJIMA, SEIGORO HAYASHI
1972 Volume 20 Issue 8 Pages
1824-1826
Published: August 25, 1972
Released on J-STAGE: March 31, 2008
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MICHIYA KIMURA, KAZUAKI HARITA, TOSHIAKI MIURA
1972 Volume 20 Issue 8 Pages
1829-1832
Published: August 25, 1972
Released on J-STAGE: March 31, 2008
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FUMIO YONEDA, YOSHIHARU SAKUMA, MISUZU ICHIBA, KAZUKO SHINOMURA
1972 Volume 20 Issue 8 Pages
1832-1834
Published: August 25, 1972
Released on J-STAGE: March 31, 2008
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FUMIHIKO UCHIMARU, SEIZABURO OKADA, AKIRA KOSASAYAMA, TSUNEO KONNO
1972 Volume 20 Issue 8 Pages
1834-1836
Published: August 25, 1972
Released on J-STAGE: March 31, 2008
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MITSUTAKA NATSUME, MORITAKA WADA
1972 Volume 20 Issue 8 Pages
1836-1838
Published: August 25, 1972
Released on J-STAGE: March 31, 2008
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YOSHIRO KOBAYASHI, ITSUMARO KUMADAKI, AKIO OHSAWA, TAKESHI YAMADA
1972 Volume 20 Issue 8 Pages
1839
Published: August 25, 1972
Released on J-STAGE: March 31, 2008
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KINZO NAGASAWA, HISAE YOSHIDOME
1972 Volume 20 Issue 8 Pages
1840-1842
Published: August 25, 1972
Released on J-STAGE: March 31, 2008
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ITSUO YOSHIZAWA, MIHOKO TAMURA, MICHIYA KIMURA
1972 Volume 20 Issue 8 Pages
1842-1843
Published: August 25, 1972
Released on J-STAGE: March 31, 2008
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MASAHARU HIRATA, AKIRA TANAKA
1972 Volume 20 Issue 8 Pages
1844-1845
Published: August 25, 1972
Released on J-STAGE: March 31, 2008
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TAKENORI TANIMURA, YASUHIKO KASAI, ZENZO TAMURA
1972 Volume 20 Issue 8 Pages
1845-1847
Published: August 25, 1972
Released on J-STAGE: March 31, 2008
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