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Volume 26, Issue 12
Displaying 1-49 of 49 articles from this issue
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YUKIO ISHIDA, HIROKO KASAHARA, SHIGERU KOBAYASHI, MASARU KIHARA1978 Volume 26 Issue 12 Pages 3603-3608
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPreviously N-methyl-5, 6, 7, 8-tetrahydrodibenz [c, e] azocine (DA-VIII-Me) and N-methyl-10, 11-methylenedioxy-5, 6, 7, 8-tetrahydrodibenz [c, e] azocine (DA-VIII-M-Me) were found to have strong α-adrenolytic activities ; the pAs values were 8.76 and 7.71, respectively. N-Benzyl-N-methyl-β-phenethylamine (BMPA) and N-benzyl-N-methyl-3, 4-methylenedioxy-β-phenethylamine (BMPA-MO) which resemble DA-VIII-Me and DA-VIII-M-Me in structure but with the azocine ring opened at the biphenyl bond, were synthesized. It was found that the α-adrenolytic activities of these compounds on rat aortic strips were much less than those of DA-VIII-Me and DA-VIII-M-Me ; the pA2 values for BMPA and BMPA-MO were 6.79 and 5.78, respectively. Thus it was concluded that the dibenz [c, e] azocine structure of the latter compounds was important for their α-adrenolytic activities. It was also found that BMPA and BMPA-MO had a dual action, producing a moderately strong long-lasting contraction and inhibiting the contractile responses to various stimulants of isolated smooth muscles.View full abstractDownload PDF (702K) -
NAOKI NAMBU, KYOKO KIKUCHI, TAKAAKI KIKUCHI, YASUYUKI TAKAHASHI, HARUH ...1978 Volume 26 Issue 12 Pages 3609-3612
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNonsteroidal antiinflammatory drugs are generally very slightly soluble in water and sometimes cause an adverse reaction due to a stimulant property to stomach upon oral administration. The present study was attempted to investigate the effect of inclusion with β-cyclodextrin (β-CD) on the irritation to stomach of three kinds of drugs, i.e., indomethacin (IMC), flufenamic acid (FFA) and phenylbutazone (PBZ) using Wistar male rats. The samples of the inclusion compounds or the intact ones were administered to stomach of rats, and the degree of injury of mucosa of stomach was observed by a dissection microscope, being evaluated by the six grades of numerical marks from 0 to 4.0. Any significant difference was not observed between the freeze-dried inclusion compounds and intact drugs of both IMC and FFA. There observed no significant difference between the two dosages of IMC. In the case of PBZ, however, there was a significant difference between the freeze-dried inclusion compound and intact drug by t-test at 5% level, suggesting that owing to its basic property the inclusion compound was effective in reducing the stomach injury due to the drug.View full abstractDownload PDF (473K) -
SHIRO YAMAMURA, KUNIYUKI ODA, TOMISHIGE MIZOGUCHI, SEIICHI SAITO, YOSH ...1978 Volume 26 Issue 12 Pages 3613-3623
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe synthesis and adrenergic activity of the stereoisomeric aryl-substituted 1-aminotetralins (3, 4, and 7) and 1-aminoindans (5 and 6), rigid structures related to the benzylamine derivatives (2), are presented. Among this series of compounds tested, trans-5, 6-dihydroxy-1-methylamino-2-(3, 4, 5-trimethoxyphenyl)-1, 2, 3, 4-tetrahydronaphthalene (3b) was the most active tracheal relaxing compound, which was approximately ten times as active as the corresponding cis isomer (4b) and about two times as active as 2b. The structure-activity relationship in this series is discussed.View full abstractDownload PDF (1295K) -
USHIHO MATSUMOTO, AKIRA KUNUGI, YUZO NAGASE1978 Volume 26 Issue 12 Pages 3624-3632
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSInteraction between corticosteroids and human erythrocytes, and the mode of incorporation of corticosteroids into erythrocytes were examined by electrophoresis, gel filtration, and other chromatographic methods, in combination with the double isotope derivative dilution method. Corticosteroids were incorporated into erythrocytes in physiological saline and subfractions of erythrocytes were separated and analyzed by the above methods. For example, cortisol was found to be bound or adsorbed on the erythrocyte surface layer to 38% (55.8% bound and 44.2% adsorbed), incorporated into the membrane to 1.7% (50% in free form, 40% bound to lipid, and 10% bound to protein), and 25.3% incorporated into the internal fluid of the cell (60% in free form and 40% bound to hemoglobin and other internal fluid components). These results indicated that a part of corticosteroids is adsorbed in the free form on the erythrocyte surface and also bound to sialoglycoprotein, and also incorporated into the membrane by binding with membrane components, lipid and protein. Further, the steroids are transported into the internal fluid by penetration through the membrane, a part of which are bound to hemoglobin and other internal fluid components and others are present in the free form. Thus, the passage of corticosteroids through the erythrocyte membrane is a passive and nonspecific transport, which, would be based on the diffusion restricted by a lipid barrier and diffusion facilitated by lipid and protein in the membrane as a carrier according to the classification of Park.View full abstractDownload PDF (1026K) -
AKIO OHSAWA, TOMIO UEZU, HIROSHI IGETA1978 Volume 26 Issue 12 Pages 3633-3640
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHitherto unaccessible acylmethylpyridazines have been prepared by means of acylation of pyridazinylmethyllithiums prepared from methylpyridazines and lithium diisopropylamide. Their tautomeric characters were examined by means of nuclear magnetic resonance, ultraviolet and infrared spectra. The tautomerisms between keto and isomeric forms were observed and the structure of the isomeric form was proposed to be the hydrogen-bonded keto-enamine (i.e., NH-methide) structure.View full abstractDownload PDF (782K) -
YUKIHIRO SHOYAMA, ITSUO NISHIOKA1978 Volume 26 Issue 12 Pages 3641-3646
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new spiro-compounds, cannabispirol and acetyl cannabispirol, were isolated along with cannabispirone and cannabispirenone from the Japanese domestic cannabis and these structures were elucidated. The biogenetic relationship of spiro-compounds and cannabinoids was also discussed.View full abstractDownload PDF (643K) -
SACHIKO TOKUHISA, KUMIYO SAISU, HARUHISA YOSHIKAWA, TOSHIHARU TSUDA, T ...1978 Volume 26 Issue 12 Pages 3647-3651
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe technique of mass fragmentography was applied to the determination of deuterated L- and D-phenylalanine loaded in animals. Method I : L-Phe-d5 or D-Phe-d5 is injected into the rat intravenously and the labeled compound in the plasma is measured at appropriate intervals with L-Phe-d8 as an internal standard. Method II : Equimolar mixture of L-Phe-d8 and D-Phe-d5 is injected into the rat intravenously and the isomers in the plasma are measured simultaneously by the double dilution method. The values obtained by the two different methods agreed well. In the distribution, however, a large difference between L- and D-forms was recognized.View full abstractDownload PDF (525K) -
MAMORU NOGUCHI, MICHINORI KUBO, TERUAKI HAYASHI, MEIZI ONO1978 Volume 26 Issue 12 Pages 3652-3657
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPrecipitation reaction of glycyrrhizin (I) with 32 kinds of alkaloids including synthetic bases and 10 kinds of crude drugs which contain various types of alkaloids in aqueous solution was investigated and following results were obtained. 1) Tertiary alkaloids which had heterocyclic aromatic rings or nitrogen atoms neighbouring to aromatic ring or conjugated olefine systems in the structure, namely, papaverine, noscapine, emetine, O-methyl domesticine, domesticine, nornuciferine, dl-tetrahydroberberine, l-corydaline, quinine, reserpine and sinoactine gave precipitate, while other types of alkaloids, namely, l-ephedrine, N-methylephedrine, l-phenylalaninol, atropine, l-scopolamine, cocaine, morphine, ethylmorphine, codeine, hydrocodeine, thebaine, sinomenine, aconitine, physostigmine, caffeine, pethidine did not. 2) Tertiary alkaloids which had pKa values smaller than 7.5 were likely to precipitate with I, while those which had pKa values larger than 7.5 did not. 3) Among quaternary alkaloids, berberine and coptisine produced precipitate, while menisperine, N-methyl scopolamine and neostigmine did not. 4) Among crude drugs which contained various alkaloids, coptis rhizome, corydalis roots, phellodendron cortex and evodia fruits gave precipitate with I in aqueous solution, while aconite roots, areca seeds, ephedra herb, magnolia cortex, nupharis rhizome and sinomenium roots did not.View full abstractDownload PDF (614K) -
FUMIYOSHI ISHIKAWA, AKIRA KOSASAYAMA, SHIGETAKE NAKAMURA, TSUNEO KONNO1978 Volume 26 Issue 12 Pages 3658-3665
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of 2-benzylaminoethylamine (1a) with cyanogen bromide was investigated under various conditions to obtain desired 1-benzyl-2-iminoimidazolidine (2a) in quantitative yield. In addition, in the presence of base this reaction gave 3-carbamoyl derivative (3a) or 3-methoxyformimidoyl derivative (6) of 2a. The 3-carbamoyl group of 3a was rearranged to the 2-imino group on heating to give 2-carbamoylimino derivative (5a). On the other hand, 6 was derived to 3a or 3-methoxycarbonyl derivative (7) by heating under strong or mild acidic medium, respectively. 3-Amidino-1-benzyl-2-iminoimidazolidine (9) was prepared through 2-benzylaminoethylguanidine (8) from 1a. 1-Benzyl- or 1-benzhydryl-2-cyanoimino-1, 3-diazacycloalkanes (10) having five-, six- and seven-membered ring size were obtained on heating of 1 with dimethyl cyanoimidodithiocarbonate and then the cyano group of 10 was selectively removed to yield 1-benzyl- or 1-benzhydryl-2-imino-1, 3-diazacycloalkanes (2). Some of 1-substituted 2-imino-1, 3-diazacycloalkane derivatives showed hypoglycemic activity.View full abstractDownload PDF (871K) -
FUMIYOSHI ISHIKAWA, AKIRA KOSASAYAMA, TSUNEO KONNO1978 Volume 26 Issue 12 Pages 3666-3674
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSynthesis of acyl and alkyl derivatives of 1-benzyl or 1-benzhydryl-2-imino-1, 3-diazacycloalkanes (1) was attempted. Acetylation of 1a, c having five-membered ring with ethyl acetate gave 2-acetyl derivatives. However, reactions of 1a, c with dialkylcarbonate, acyl chloride and alkyl or aryl isocyanate afforded a mixture of 2- and 3-substituted compounds and reactions of 1a, c with isothiocyanate derivatives gave predominantly 3-substituted compounds. On the other hand, 1b, d having six-membered ring gave predominantly 2-substituted compounds by the similar reactions. Direct alkylation of 1a, c with alkyl iodide in the presence of sodium hydride yielded 3-alkyl derivatives (5). In the similar alkylations, 2-alkoxycarbonylimino and 2-cyanoimino derivatives, 2 and 9, gave 3-alkyl compounds 7 and 8, in which 2-alkaxycarbonyl and 2-cyano groups were removed on heating in t-butanol containing a small amount of hydrochloric acid to give 5 in good yields. Heating 7 and 8 having 1-benzhydryl group with sodium hydride gave 2-oxo- or 2-imino-3, 3-diphenylimidazo [1, 2-a] [1, 3] diazacycloalkane derivatives (10, 11 and 12). Some of 1-substituted 3-acyl and 3-alkyl-2-imino-1, 3-diazacycloalkanes showed hypoglycemic activity.View full abstractDownload PDF (935K) -
KENTARO HIRAI, TERUYUKI ISHIBA, HIROHIKO SUGIMOTO, TETSUYA TAKAHASHI, ...1978 Volume 26 Issue 12 Pages 3675-3681
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMethylsulfinylethylthiamine (MSIT) (I) was found to be converted readily into a mixture of disulfides in aqueous solution at pH 7-8. Disulfides II and III were isolated and their structures were confirmed to be MSIT-disulfide and MTETDS (methylthioethyl-thiaminedisulfide), respectively. Disulfide IV could not be isolated in a pure state, but rapid disproportionation into a mixture of II and III suggested that IV is a mixed disulfide of MSIT and MTET. In buffer solution at pH 8, the disappearance of MSIT followed first-order kinetics with 2.53×10-3 sec-1 at 60°, and the activation energy was found to be 23.8 kcal/mol. Clearly, the sulfoxide group in MSIT plays an important role in this transformation reaction. In the proposed reaction route, MSIT reacts with two mol of alkali to produce ring opened thiol and intramolecular thiol-sulfoxide interaction occurs to form an unstable thiol-sulfoxide adduct that is rapidly destroyed by reaction with another molecule of thiol to give an unsymmetrical disulfide (IV). Disproportionation of IV follows to afford a mixture of symmetrical disulfides II and III. Independent synthesis of II and III was also achieved via halogeno-SB1. Compounds II and III show high anticoccidial activities against avian coccidiosis.View full abstractDownload PDF (817K) -
YOSHIKI HAMADA, MICHIHARU SUGIURA1978 Volume 26 Issue 12 Pages 3682-3694
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSChemical reactivity of quinoline and isoquinoline skeletons was compared, using 1-cyano-2-methoxy-1, 2-dihydroquinoline (2a), 2-cyano-1-methoxy-1, 2-dihydroisoquinoline (2b), 3-bromo-1-cyano-2, 4-dimethoxy-1, 2, 3, 4-tetrahydroquinoline (3a), and 4-bromo-2-cyano-1, 3-dimethoxy-1, 2, 3, 4-tetrahydroisoquinoline (3b), in order to know the fundamental chemical characteristics of 2a, b and 3a, b for use as an intermediate for the syntheses of nitrogen-containing heterocyclic compounds. 1) Oxidation of 2a or 2b and 3b afforded 2-one compound or 1-one compounds. 2) Reaction of 2a or 2b with ethanethiol afforded 1 (or 2)-cyano-2 (or 1)-ethylthio-1, 2-dihydroquinoline (2e) or -1, 2-dihydroisoquinoline (2f). Reaction of 3a with ethanethiol gave 4-bromo-2-cyano-1-ethylthio-3-methoxy-1, 2, 3, 4-tetrahydroisoquinoline (3i) but 3b did not react with this reagent. 3) Bromination of 2e and 2f in methanol respectively gave 3a and 3b. 4) Reaction of 2-cyano-3, 4-dibromo-1-methoxy-1, 2, 3, 4-tetrahydroisoquinoline (3c) with ethanethiol or diethylamine afforded 3-bromo-2-cyano-1, 4-diethylthio-1, 2, 3, 4-tetrahydroisoquinoline (3d) or 4-bromo-2-cyano-3-diethylamino-1-methoxy-1, 2, 3, 4-tetrahydroisoquinoline (3g). 5) Alkaline hydrolysis of 3d and 3i produced 1-ethylthioisoquinoline. Acid hydrolysis of 3b, d, g, i resulted in the formation of isoquinolines with the 4-substituent intact. 6) Alkaline hydrolysis of 3b or 3d in alcohol afforded N-iminoethers, while similar reaction in hydrogen peroxide N-carboxamides.View full abstractDownload PDF (1014K) -
TOHRU HINO, HIDETOSHI MIURA, RYOICHI MURATA, MASAKO NAKAGAWA1978 Volume 26 Issue 12 Pages 3695-3703
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOxidative cyclization of 3-indolepropanethiol (6) and 3-indolepropanol (9) with N-bromosuccinimide or N-chlorosuccinimide (NCS) gave the corresponding thiopyrano-[2, 3-b] indole (7) and pyrano [2, 3-b] indole (10) in good yields. Reaction of 7 with NCS in carbon tetrachloride gave an unstable chloroindolenine (18) which transformed to a spirooxindole (19) on treatment with ethanolic hydrochloric acid. Reaction of 7 with NBS in carbon tetrachloride gave 7-bromo derivative (20) via the 3-bromoindolenine. Similarly pyranoindole (10) gave a spirooxindole (23) in good yield on treatment with NCS in methylene chloride followed by the addition of ethanolic hydrochloric acid. On the other hand reaction of 9 with two equivalents of NCS gave 23 and dichlorooxindole (24). Dye-sensitized photooxygenation of 3-indolepropanol (9) in benzene gave 4a-hydroxypyrano [2, 3-b] indole instead of 10.View full abstractDownload PDF (1040K) -
KOJI YAMAKAWA, TSUYOSHI SATOH1978 Volume 26 Issue 12 Pages 3704-3714
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTotal syntheses of (±)-furanoeremophilane (34), (±)-furanoligularane (37), (±)-9, 10-dehydrofuranoeremophilane (32), (±)-ligularone (1), (±)-3β-hydroxyfuranoeremophilane (25), and (±)-3β-furanoligularanol (31) are described. Reduction of cis-annulated 6, 9-dioxo-3-ketal (9) with NaBH4 gave ketols (10a and 11a). 11a was desketalized and subjected to selective reduction with P-I2 to give 3, 6-diketone (13), which was already converted into (±)-1. Reduction of 3, 9-dioxo-6α-ol (14), derived from 10a, with P-I2 afforded a mixture of 17-20. Both 3, 9-diketones (18 and 19) were converted into 3, 9-diol acetates (24b and 30b), respectively. The Birch reductions were effected for deacetoxylation of α'-acetoxy-α-substituted furan, e.g. (26) and the results are shown in Table I. Reductive deacetoxylation of 24b and 30b by the Birch procedure gave (±)-25 and (±)-31, respectively. (±)-Hydroxyfuranoeremophilane (6), derived from 18, was treated with POCL3-pyridine to give (±)-32. Reductive deacetoxylation of acetate (33) by the Birch procedure gave (±)-34. trans-Annulated 3, 9-diketone (19) was derived to the acetate (36b), which was converted by the Birch procedure into (±)-37.View full abstractDownload PDF (1229K) -
MASAJI ISHIGURO, HIROMITSU SAITO, ATSUO SAKAMOTO, NOBUO IKEKAWA1978 Volume 26 Issue 12 Pages 3715-3721
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOsmium tetroxide oxidation of the 22-olefin (4) and reaction of sodium dimethylsulfonium methylide with the 22-aldehyde (3a) afforded stereoselectively the 22S-and 22R-epoxides (7a and 7b), respectively. Those epoxide can be led to the 22R- and 22S-hydroxy steroides by Grignard reaction. Inversion of the configuration of hydroxyl group on C-22 and C-24 positions was achieved in high yield by means of superoxide displacement reaction.View full abstractDownload PDF (856K) -
ISAO KITAGAWA, HIDEAKI YAMANAKA, MOTOMASA KOBAYASHI, TAKAO NISHINO, IT ...1978 Volume 26 Issue 12 Pages 3722-3731
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe chemical structures of two antifungal oligoglycosides holotoxin A and B, which were isolated from the sea cucumber Stichopus japonicus SELENKA, have been reinvestigated. On the basis of chemical and physicochemical evidence, the genuine sapogencl of holotoxin A and B has been elucidated to be holotoxigenol rather than previously proposed stichopogenin A4 (3), and it has been shown that the structures of holotoxin A and B should be revised as 3-O-{2-O-[3-O-methyl-β-D-glucopyranosyl (1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl]-4-O-[3-O-methyl-β-D-glucopyranosyl (1→3)-β-D-glucopyranosyl]-β-D-xylopyranosyl}-holotoxigenol (6) and 3-O-{2-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl (1→4)-β-D-quinovopyranosyl]-4-O-[β-D-glucopyranosyl (1→3)-β-D-glucopyranosyl]-β-D-xylopyranosyl}-holotoxigenol (9), respectively.View full abstractDownload PDF (1172K) -
SEIICHI UESUGI, WONGYL LIMN, MORIO IKEHARA1978 Volume 26 Issue 12 Pages 3732-3737
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSConformation of dinucleoside monophosphates containing 8-methyladenosine (m8A) residue, which prefer a syn conformation, was analyzed by proton magnetic resonance studies. The dimers are 2'-5' and 3'-5' isomers of Apm8A, and m8Apm8A. The following results were obtained. The data for (2'-5') Apm8A are consistent with an anti (2')-anti (5'), right-handed stacked conformation. The data for (3'-5') Apm8A are consistent with a syn (3')-syn (5') and a high anti (3')-high anti (5') stacked conformation. The data for (3'-5') m8Apm8A can be explained by a syn (3')-syn (5') conformation with little stacking. The data for (2'-5') m8Apm8A can be explained by an anti (2')-syn (5') stacked conformation. These results are in accordance with the results of ultraviolet and circular dichroism studies.View full abstractDownload PDF (719K) -
SEIKI TANADA, KEITO BOKI1978 Volume 26 Issue 12 Pages 3738-3742
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAdsorption of methanethiol on activated carbon, magnesium silicate, and zeolite, and the rate of adsorption on them were gravimetrically measured to elucidate the mechanism of this adsorption. The Dubinin-Astakhov equation was applicable to the adsorption isotherms of methanethiol on these adsorbents. The rate of adsorption was expressed by the fractional approach to the equilibrium, and the mechanism of the rate of adsorption was explained by the volume filling of the smallest pore to the pores of a certain dimension. Activated carbon No. 2 was suitable for practical purposes because it had a high adsorption capacity at high pressure, its rate of adsorption was relatively fast, and methanethiol was physically adsorbed on it. From the results of differential heat of adsorption, adsorption of methanethiol on activated carbon No. 2 was considered to be the volume filling of micropores and the adsorption of monolayers or multilayers on transitional pores.View full abstractDownload PDF (576K) -
Useful Dethioacetalization with Soft Acid Metal Salts : Thallium Trinitrate and Mercuric PerchlorateEIICHI FUJITA, YOSHIMITSU NAGAO, KIMIYOSHI KANEKO1978 Volume 26 Issue 12 Pages 3743-3751
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDethioacetalization with thallium trinitrate (TTN) was tried on thioacetals 3-13, and good results were obtained. Then, the utility of co-solvents to be used with methanol was checked, and a wide range of co-solvents were shown to be available. The mechanism was also discussed. Subsequently, dethioacetalization with mercuric perchlorate was found to be another excellent method. This procedure provided a great success for the dethioacetalization of compounds 4 and 11 which was not successful by the TTN procedure.View full abstractDownload PDF (962K) -
HARUAKI YAJIMA, MASAHARU TAKEYAMA, JUN KANAKI, OSAMU NISHIMURA, MASAHI ...1978 Volume 26 Issue 12 Pages 3752-3757
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNG-mesitylene-2-sulfonylarginine was prepared. This protecting group was found to be quantitatively cleaved by hydrogen fluoride, methanesulfonic acid or trifluoromethanesulfonic acid and partially by hydrogen bromide in acetic acid. As a side reaction, partial mesitylenesulfonylation of the phenolic group of tyrosine was noted. However this side reaction could be suppressed by cation scavengers, anisole-thioanisole-cresol (o) (1 : 1 : 1), in less than 4%.View full abstractDownload PDF (825K) -
SEIJI KATAYAMA, YUKIO AKAHORI1978 Volume 26 Issue 12 Pages 3758-3764
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe solvent and concentration dependences of proton magnetic resonance spectra of 8-quinolinol are investigated. The resonance lines of each proton indicate the selective and specific dilution shifts in various solvents. These shifts can be successfully accounted for by assuming the specific solute-solute interactions. It can therefore be presumed that there are both a self-collision complex and a dimerized hydrogen bond formed between solutes in this system.View full abstractDownload PDF (710K) -
KIMIHIRO SHIMIZU, KIYOSHI TOMIOKA, SHUNICHI YAMADA, KENJI KOGA1978 Volume 26 Issue 12 Pages 3765-3771
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA biogenetic-type asymmetric synthesis of optically active galanthamine ((+)-4 and (-)-4) is described. Norbelladine derivative (10), having C2 symmetry in the aromatic moiety of C6-C1-N part, was prepared from L-tyrosine, and was converted to narwedinetype enone (11) by oxidation and highly specific asymmetric cyclization. Phosphorylation of phenolic hydroxyl group followed by sodium borohydride reduction afforded 14 having galanthamine skeleton. N-Methylation followed by removal of the methoxycarbonyl and phosphate moieties afforded (+)-galanthamine ((+)-4). Formal total synthesis of (-)-galanthamine ((-)-4) from L-tyrosine via enantiomeric interconversion of narwedine derivative (12) is also described.View full abstractDownload PDF (897K) -
TADANORI MAYUMI, HIROKO KAWANO, YOSHIKO SAKAMOTO, ETSUJI SUEHISA, YUIC ...1978 Volume 26 Issue 12 Pages 3772-3778
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe high performance liquid chromatographic procedure was established for the determination of ergothioneine in biological materials. The procedure is also applicable to the purification of 3H-ergothioneine. The metabolism of ergothioneine given to rats was very slow ; the ergothioneine was not disappear even after 1 week fasting. The ergothioneine administrated was mostly concentrated in the liver and the level was 10 times as high as that in blood. All ergothioneine in the blood was found in blood corpuscles 24 hr after the administration.View full abstractDownload PDF (747K) -
KANETO UEKAMA, FUMITOSHI HIRAYAMA, HARUMI TANAKA, KATSUMI TAKEMATSU1978 Volume 26 Issue 12 Pages 3779-3784
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe pKa and intrinsic partition coefficient (PC0) of seven prostaglandins (PGE1, PGE2, PGA1, PGA2, PGB1, PGB2, and PGF2a) were determined from their pH-partition profiles. Structural changes of the prostaglandins were largely reflected in PC0 values rather than the pKa values. Partition of the prostaglandins from aqueous buffer (pH7.0) to cyclohexane containing various alcohols was markedly enhanced by the addition of aliphatic amines in aqueous phase. The influences of temperature and chain length of both alcohol and amine on partition coefficients of the prostaglandins were investigated. Furthermore, extraction constants (Ke) for prostaglandin-amine ion pairs and number of alcohol molecules associated with ion pair (n) were determined to gain insight into the mechanism of enhanced extraction process.View full abstractDownload PDF (601K) -
YUKIO KAMEDA, TOSHIKATSU NAKABAYASHI, SHOICHI KANATOMO, SEIMEI KITADE1978 Volume 26 Issue 12 Pages 3785-3791
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe acylase of Ehrlich ascites carcinoma cells was purified by fractionation with ammonium sulfate, diethylaminoethyl cellulose chromatography, Sephadex. G-200 gel filtration, and hydroxylapatite chromatography. The acylase activity of the purified enzyme toward N-dichloroacetyl-L-aspartic acid was 1561 U/mg and it was represented about 410 fold purification over the cell free extract. The enzyme has a pH optimum around 8.5 toward N-dichloroacetyl-L-aspartic acid. It is inhibited by Sn2+, Mn2+, Cu2+, Hg2+, Zn2+, p-chloromercuribenzoate, ICH2COOH, H2O2, and diisopropyl fluorophosphate. As a result of the investigation of substrate specificity, it was found that the enzyme hydrolyzed only N-dichloroacetyl-L-aspartic acid among eleven kinds of N-dichloroacetyl amino acids. But it could not hydrolyze D from of N-dichloroacetyl-aspartic acid. In order to test the effect of acyl groups toward the enzyme activity, eleven acyl aspartic acids were tested. N-Chloroacetyl, N-dichloroacetyl, N-trifluoroacetyl derivatives of L-aspartic acid were hydrolyzed.View full abstractDownload PDF (728K) -
KIYOSHI HATA, KIMIYE BABA, MITSUGI KOZAWA1978 Volume 26 Issue 12 Pages 3792-3797
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe heartwood of Cassia garrettiana CRAIB. (Leguminosae), one of the Thai drugs being used as a mild cathartics in the folk medicine, afforded a new anthrone-C-glycoside named cassialoin, together with anthraquinones which were identified as chrysophanol, chrysophanol benzanthrone with the structure of 4-methyl-6, 8-dihydroxy-7H-benz [de]-anthracen-7-one, chrysophanol dianthrone and (-)-11-deoxyaloin, as well as various phenolic compounds. The structure of cassialoin was established as 10-hydroxy-10-C-D-glucosylchrysophanol-9-anthrone.View full abstractDownload PDF (838K) -
YOSHINOBU GOTO, NORIKO HONJO1978 Volume 26 Issue 12 Pages 3798-3806
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of 4-phenyloxazole 3-oxides (III) with arylisocyanates afforded imidazolin-[4, 5-d] oxazolid-2-one derivatives (Vaa-Vbc). On pyrolysis of Vaa, Vab and Vba, a rearrangement of methyl group on the 5-position of imidazoline ring to yield imidazolinones (VIaa, VIab and VIba) was observed. When imidazolinones were treated with large excess of NaBH4, reduction of ring amide group occurred.View full abstractDownload PDF (815K) -
KEIJI KOMAKI, TOSHINOBU KAWATA, KAZUNOBU HARANO, TANEZO TAGUCHI1978 Volume 26 Issue 12 Pages 3807-3814
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMigration of alkyl group from O to S in the reaction of O, S-dialkyl dithiocarbonates with boron trifluoride etherate was studied to elucidate the reaction mechanism on the basis of results from kinetics, crossover reaction, and products formed. It was worthy of note that dialkyl methyl sulfonium fluoroborates were formed in a fairly good yield in reactions with O-alkyl S-methyl dithiocarbonates (alkyl=benzyl and cholesteryl) with boron trifiuoride etherate. Formation mechanism of these by-products was investigated and discussed.View full abstractDownload PDF (799K) -
TETSUJI KAMETANI, KIMIO TAKAHASHI, MASATAKA IHARA, KEIICHIRO FUKUMOTO1978 Volume 26 Issue 12 Pages 3815-3819
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of the 2, 3-dihydro-1H-pyrrolo [1, 2-a] indoles (1 and 7) with N-bromosuccinimide in protic solvents such as methanol and acetic acid yielded the brominated compounds (4 and 8). The reaction of the pyrrolo [1, 2-a] indole-5, 8-diones (9-13) with N-bromosuccinimide in these solvents afforded the adducts (14-18 and 20-21). Debromination of the brominated compounds (5b, 15, 16 and 20) with tri-n-butyltin hydride was also described.View full abstractDownload PDF (689K) -
TETSUJI KAMETANI, MASATOSHI CHIHIRO, MITSUHIRO TAKESHITA, KIMIO TAKAHA ...1978 Volume 26 Issue 12 Pages 3820-3824
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCycloaddition of 1-acetoxybenzocyclobutene (21) with naphthoquinone (8) gave naphthacene-5, 12-quinone (22) which was converted into 6, 11-dihydroxynaphthacene-5, 12-quinone (25) by three steps. Synthetic trial of 6-oxygenated naphthacene-5, 12-quinones from naphthacene-5, 12-quinones are also described.View full abstractDownload PDF (619K) -
ISAO KITAGAWA, AKIKO KADOTA, MASAYUKI YOSHIKAWA1978 Volume 26 Issue 12 Pages 3825-3831
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBy employing the oxidative decarboxylation reaction using lead tetraacetate and successive nitromethane cyclization reaction in the reaction sequence, N-acetyl-D-glucosamine (11a) has been converted to hexaacetyl-streptamine (20a) in 8% overall yield. It has been also suggested that the present transformation would provide a versatile method for preparation of aminocyclitols from various types of uronic acids.View full abstractDownload PDF (852K) -
YASUO SHIBATA, YUKIKO TATSUNO, TOKUHIKO HIGASHI1978 Volume 26 Issue 12 Pages 3832-3835
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRats were treated with ginsenoside-Rb1 or -Rc, purified saponins from Ginseng, given intraperitoneally at a dose of 5mg per 100g body weight, and the incorporation of 14C-amino acids or of 14C-fatty acids was studied with adipose, intestine, liver, kidney, spleen and serum. The stimulation in protein synthesis by the ginsenoside was observed in the intestine and the liver, and that in lipid metabolism was detected in adipose tissue as well as intestine and liver. These three organs are assumed to be target organs of the ginsenoside, and the latter two to be probable sites for apolipoprotein synthesis.View full abstractDownload PDF (515K) -
YASUYUKI TAKAHASHI, NAOKI NAMBU, TSUNEJI NAGAI1978 Volume 26 Issue 12 Pages 3836-3842
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSInteraction between several nonsteroidal antiinflammatory drugs and pectin was studied by the centrifugation method, the equilibrium dialysis method and the solubility method. Benzydamine hydrochloride (BZM) and ketoprofen (KPF) formed coprecipitates with pectin by the centrifugation method, and the binding isotherms of BZM and pectin showed a multi-layer type. On the other hand, the binding isotherm of BZM to pectin by the equilibrium dialysis method showed a Langmuir type in low equilibrium concentration range and the saturated amount bound decreased with an increase of ion concentration of the solution. The solubility of all drugs used decreased with an increase of concentration of pectin. IR absorption spectroscopy, X-ray diffraction pattern and differential scanning calorimetry of the BZN/pectin coprecipitate showed clear difference from the physical mixture. The dissolution rate of BZM/pectin coprecipitate and physical mixture of BZM and pectin was very slow in comparison with intact BZM and physical mixture of BZM and galacturonic acid. Pectin forms water insoluble complexes with these nonsteroidal antiinflammatory drugs, suggesting a usefulness as an additive for sustained-release preparations, and this might afford a mean for reducing adverse reactions of nonsteroidal antiinflammatory drugs to stomach after oral administration.View full abstractDownload PDF (754K) -
KIYOTO EDO, TAKAO SAKAMOTO, HIROSHI YAMANAKA1978 Volume 26 Issue 12 Pages 3843-3850
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe pyrimidine derivatives containing an acetylenic side chain were synthesized by means of the reaction of alkyl-(or phenyl) acetylenes with twelve kinds of 2-, 4-, and 5-iodopyrimidines in the presence of a palladium triphenylphosphine complex in satisfactory yields. When propargyl alcohol was used, the reaction exhibited the tendency of decreasing the yield. The reaction readily proceeded in both 2, 4-diiodo- and 4, 6-diiodo-pyrimidines to give the corresponding dialkynyl derivatives. This acetylene coupling reaction was applicable to the synthesis of the 4-quinazoline derivatives.View full abstractDownload PDF (871K) -
TOSHIO NAMBARA, HIROSHI HOSODA, KYOICHI TADANO, KOUWA YAMASHITA1978 Volume 26 Issue 12 Pages 3851-3855
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to obtain the specific antiserum for the use of radioimmunoassay of 5α-dihydrotestosterone a new hapten-carrier conjugate was prepared from 15α-hydroxy-5α-dihydrotestosterone 15-hemisuccinate by coupling with bovine serum albumin employing the mixed anhydride technique. The specificity of anti-5α-dihydrotestosterone antiserum elicited in the rabbit by immunization with this antigen was tested by cross-reaction studies with the closely related steroids. The results indicated that specific antiserum which is capable of differentiating 5α-dihydrotestosterone from testosterone and 5α-androstane-3β, 17β-diol to a certain extent would be produced by antigen whose steroidal moiety is linked to an immunogenic protein through the position remote from the inherent functional groups on the steroid nucleus.View full abstractDownload PDF (636K) -
MASATOMO HAMANA, SETSUKO KUMADAKI1978 Volume 26 Issue 12 Pages 3856-3862
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of 4-nitroquinoline 1-oxide (1) with potassium cyanate in hot ethanol afforded 4-ethoxyquinoline 1-oxide. On the other hand when potassium cyanide was applied instead of the cyanate, the reaction followed an alternate course giving 3-cyano-4-quinolinol (3). Compound 3 was produced also from reactions in 90% ethanol, DMF, DMSO and dioxane, the best yield being obtained from the reactions in DMF at 80-90°. It was further disclosed that besides 1, 2-chloro-(13), 2-bromo-4-nitroquinoline 1-oxides (14), 4-nitroquinoline (18) and 2-bromo-4-nitroquinoline (19) underwent the same type of reaction.View full abstractDownload PDF (800K) -
MANKI KOMATSU, ICHIRO YOKOE, YOSHIAKI SHIRATAKI1978 Volume 26 Issue 12 Pages 3863-3870
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new flavonoid compounds, named sophoraisoflavanone A (I), mp 178-180°, C21H22O6, and sophoraflavanone B (II), mp 193-195°, C20H20O5, together with sophoronol (IV), isosophoranone (V) and isobavachin (VI) were isolated from the aerial parts of Sophora tomentosa L. Besides them, a new phenolic compound (III), mp 108-110°, C27H44O4, was also isolated. The structures of them were determined by chemical and spectroscopic studies. Sophoraisoflavanone A (I) exhibited antifungal activity.View full abstractDownload PDF (872K) -
SHIGEO UKAI, TADASHI KIHO, CHIHIRO HARA1978 Volume 26 Issue 12 Pages 3871-3876
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe acidic heteroglycans (AC and BC) prepared from the fruit bodies of Tremella fuciformis BERK have been partially hydrolyzed with 1 N sulfuric acid to isolate three kinds of acidic oligosaccharides (H-1, H-2 and H-3). On the basis of methylation analysis and PMR spectroscopy, the structures of these compounds were established to be O-(β-D-glucopyranosyluronic acid)-(1→2)-O-α-D-mannopyranosyl-(1→3)-O-α-D-mannopyranosyl-(1→3)-D-mannopyranose for H-1, O-(β-D-glucopyranosyluronic acid)-(1→2)-O-α-D-mannopyranosyl-(1→3)-D-mannopyranose for H-2, and 2-O-(β-D-glucopyranosyl uronic acid)-D-mannopyranose for H-3. The chemical and physical properties of H-3 were identical with those reported for the aldobiouronic acid prepared from the extracellular polysaccharides of T. mesenterica and other sources. These results indicate that the anomeric configuration of the non-reduced terminal D-glucopyranosyluronic acid residues of the acidic polysaccharides, AC and BC, is of β-type, and that the configuration of internal D-mannopyranose residues is of α-type. The present study also confirms that β-D-glucopyranosyluronic acid residues are linked to the position 2 of α-1→3 D-mannopyranose units in both AC and BC.View full abstractDownload PDF (740K) -
TETSUZO KATO, TOSHIYUKI CHIBA, MASAYUKI SATO1978 Volume 26 Issue 12 Pages 3877-3879
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of diketene with benzaldehyde (1) in the presence of sulfuric acid gives α-benzylideneacetoacetic acid (5). Similarly, reaction of diketene with cinnamaldehyde (2) and β-phenylcinnamaldehyde (3) gives 2-acetyl-5-phenyl-2, 4-pentadienoic acid (6) and 2-acetyl-5, 5-diphenyl-2, 4-pentadienoic acid (7), respectively.View full abstractDownload PDF (436K) -
TETSUZO KATO, HITOSHI KIMURA, KENICHI TANJI1978 Volume 26 Issue 12 Pages 3880-3883
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEthyl 4-bromo (and chloro)-3-oxobutanoate (1 and 2) reacts with diethyl malonate in the presence of sodium hydride to give diethyl 5-ethoxycarbonyl-3-oxohexanedioate (3) and diethyl 5-carboxy-3-oxohexanedioate (4). Similarly, reaction of the haloester (1, 2) with methyl cyanoacetate gives 1-ethyl methyl 5-cyano-3-oxohexanedioate (6) and 1-ethyl hydrogen 5-cyano-3-oxohexanedioate (7). On the other hand, 1 reacts with malononitrile in the presence of triethylamine to give ethyl 5-amino-4-cyanofuran-2-acetate (8) and ethyl 3-amino-2, 4, 4-tricyano-2-cyclopenten-1-ylideneacetate (9).View full abstractDownload PDF (540K) -
SHOZO KAMIYA, MICHIKO MIYAHARA, SHOKO SUEYOSHI, IKUO SUZUKI, SHIGEYOSH ...1978 Volume 26 Issue 12 Pages 3884-3888
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of 1-(2-chloroethyl)-1-nitroso-3-(3-pyridylmethyl) urea (Ia) and the 3-nitroso isomer (Ib) with m-chloroperbenzoic acid, gave the corresponding N-oxides, IIa and IIb. The 3-nitrosoureas (Ib, IIb) isomerized to the 1-nitroso isomers (Ia, IIa) by dissolving them in formic acid. The reaction of 6-bis (2-chloroethyl) aminomethyl-3-hydroxypyridazine 1-oxide (III) with bromine gave the 4-bromo derivative (IV). 1-(2-Chloroethyl)-1-nitroso-3-(3-pyridylmethyl) urea N-oxide (IIa) showed the most marked activity against rat ascites hepatom AH-13 and mouse lymphoid leukemia L-1210.View full abstractDownload PDF (622K) -
HITOSHI UNO, MIKIO KUROKAWA1978 Volume 26 Issue 12 Pages 3888-3891
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe bromination, the nitration, the chlorosulfonation, the formylation and the Mannich reaction of 1, 2-benzisothiaizol-3-acetic acid (1) were investigated and it was shown that the 3α-methylene group is also activated to the electrophilic substitutions as in 1, 2-benzisoxazol-3-acetic acid.View full abstractDownload PDF (558K) -
MASASHI OKADA, EMAKO SUZUKI, MINORU IIYOSHI1978 Volume 26 Issue 12 Pages 3891-3896
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNineteen N-alkyl-N-(hydroxy- or oxo-alkyl) nitrosamines structurally related to N-butyl-N-(4-hydroxybutyl) nitrosamine, a potent bladder carcinogen, were synthesized for the purpose of investigating their carcinogenic effects in rats. They are N-alkyl-N-(4-hydroxybutyl) nitrosamines, N-alkyl-(3-hydroxypropyl)-nitrosamines, N-alkyl-N-(2-hydroxyalkyl) nitrosamines, and N-alkyl-N-(2- or 3-oxoalkyl) nitrosamines. They were mostly prepared by the nitrosation of the corresponding N-alkyl-N-(hydroxyalkyl) amines. The nitrosamines with an oxo group were prepared by chromium trioxide oxidation of the corresponding N-alkyl-N-(hydroxyalkyl) nitrosamines with a secondary hydroxyl group.View full abstractDownload PDF (729K) -
TOSHIO UNO, KANAME TAKAGI, MUNEMITSU TOMOEDA1978 Volume 26 Issue 12 Pages 3896-3901
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFurazanobenzothiadiazole and related compounds were prepared by a new synthetic route starting from 4, 7-dibromo-5-nitrobenzo-2, 1, 3-thiadiazole, which was obtained in good yield by nitration of 4, 7-dibromobenzo-2, 1, 3-thiadiazole easily acessible. Some chemical reactions of this tricyclic ring system-ring opening reaction, photo-cleavage reaction, bromination and reduction-were discussed.View full abstractDownload PDF (742K) -
MINORU KUBOTA, TADAMASA HIRAYAMA, OSAMU NAGASE, HARUAKI YAJIMA1978 Volume 26 Issue 12 Pages 3901-3904
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe nonadecapeptide corresponding to δ-endorphin, a plasmin hydrolysate of porcine β-lipotropin, was synthesized using protecting groups removable by methanesulfonic acid. Analgesic activity of the synthetic peptide was estimated as active as Leu-enkephalin by the tail pinch method.View full abstractDownload PDF (568K) -
MASATAKA MOCHIZUKI, TAKAKO ANJO, MASASHI OKADA1978 Volume 26 Issue 12 Pages 3905-3908
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSyntheses of a series of new N, N-dialkylnitrosamines monosubstituted at the α-carbon with an acetoxy group were reported. They were prepared by the procedures reported earlier, but a new procedure was provided, according to which N-alkyl-N-(methoxymethyl)-nitrosamines were converted into N-alkyl-N-(acetoxymethyl) nitrosamines in low but satisfactory yield by refluxing them in acetic acid. The (E)-(Z) conformer ratios of these compounds determined by nuclear magnetic resonance measurement were given.View full abstractDownload PDF (550K) -
MASASHI OKADA, EMAKO SUZUKI, MINORU IIYOSHI1978 Volume 26 Issue 12 Pages 3909-3913
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFourteen N-alkyl-N-(ω-carboxyalkyl) nitrosamines related to N-butyl-N-(3-carboxypropyl) nitrosamine, principal urinary metabolite of a potent bladder carcinogen N-butyl-N-(4-hydroxybutyl) nitrosamine, were prepared for the purpose of mainly characterizing urinary metabolites and in part testing their carcinogenic effects in rats. They were N-alkyl-N-(3-carboxypropyl) nitrosamines, N-alkyl-N-(2-carboxyethyl) nitrosamines, and N-alkyl-N-(carboxymethyl) nitrosamines. They were mostly prepared by the permanganate oxidation of the corresponding N-alkyl-N-(ω-hydroxyalkyl) nitrosamines.View full abstractDownload PDF (648K) -
MASATAKA MOCHIZUKI, TAKAKO ANJO, MASASHI OKADA1978 Volume 26 Issue 12 Pages 3914-3919
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of new N-alkyl-N-(ω-acetoxyalkyl or ω-carbomethoxyalkyl) nitrosamines substituted at the α-carbon atom of the alkyl chain with an acetoxy group were synthesized as possible model compounds for metabolically activated N, N-dialkylnitrosamines.View full abstractDownload PDF (689K) -
OSAMU HOSHINO, MINORU OHTANI, BUNSUKE UMEZAWA1978 Volume 26 Issue 12 Pages 3920-3921
Published: December 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSLead tetraacetate oxidation of 1-(3', 4'-dimethoxy- or 3', 4'-methylenedioxy-benzyl)-6-hydroxy-7-methoxy-2-methyl-1, 2, 3, 4-tetrahydroisoquinoline (1a or 1b) in CH2Cl2 was found to give quantitatively a diastereomeric mixture (1 : 1) of an o-quinol acetate (2a or 2b), treatment of which with Ac2O-conc. H2SO4 at room temperature led to (±)-O-acetyl-predicentrine (5a) or -isodomesticine (5b). Furthermore, hydrolysis of 5a or 5b with 1.7% KOH-MeOH afforded (±)-predicentrine (6a) or (±)-isodomesticine (6b).View full abstractDownload PDF (355K)
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