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Volume 14, Issue 9
Displaying 1-26 of 26 articles from this issue
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Suminori Umio, Takashi Kamiya, Kazuma Nishitsuji1966 Volume 14 Issue 9 Pages 925-930
Published: September 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThiamic acid, 3-(1, 2-dicarboxyethyl)-4-methyl-5-(2-hydroxyethyl) thiazolium chloride, and an inner salt of its hydroxide were prepared from aspartic acid and 3-chloro-5-hydroxy-2-pentanone via thiazolidine-2-thione, tetrahydrofuro [2, 3-d] thiazole-2(3H)-thione, and 4-thiazoline-2-thione. Some related compounds are also synthesized. The structure of thiamic acid was confirmed by their ultraviolet spectra.View full abstractDownload PDF (654K) -
Tetsuzo Kato, Yukio Kubota1966 Volume 14 Issue 9 Pages 931-933
Published: September 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPechmann and Neger1) reported the reaction of acetonedicaboxylic acid with acetic anhydride to give dehydroacetocarboxylic acid (II), which transformed to its anilide (III) by the treatment with aniline. On the basis of chemical behavior and infrared data, we prefer the correct structures of these two being 3, 5-diacety 1-2H-pyran-2, 4, 6 (3H, 5H)- trione (V) and 1-phenyl-3, 5-diacety1-2, 4, 6-piperidinetrione (VI) respectively.View full abstractDownload PDF (407K) -
Yuichi Kanaoka, Yoshio Ban, Koichi Miyashita, Kimiko Irie, Osamu Yonem ...1966 Volume 14 Issue 9 Pages 934-939
Published: September 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPolyphosphate ester (PPE) was demonstrated to be a good agent in the Fischer indole synthesis involving various ketones and aldehydes except ones having methyl group attached to carbonyl, thus providing a convenient preparative route to 2-unsubstituted and 2, 3-disubstituted indole and indolenine derivatives.View full abstractDownload PDF (793K) -
Hidetoshi Yoshimura, Hiroshi Tsuji, Hisao Tsukamoto1966 Volume 14 Issue 9 Pages 939-947
Published: September 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMajor metabolic pathways of two series of alkylaryl ethers, i.e. 2-alkoxy-5-nitro-anisoles and alkyl p-nitrophenyl ethers, were investigated in vivo with rabbits. It was confirmed that aryl ethers of methyl or ethyl were dealkylated quickly, but of butyl or of isoamyl only with slow rate and metabolized mainly through penultimate hydroxylation pathway. Propylaryl ethers, on the other hand, behaved very differently, producing ω-oxidation product together with dealkylation and penultimate hydroxylation products. Demethylation rate of the methoxyl group attached to the meta position of nitro-substituent in 2-alkoxy-5-nitroanisoles was held nearly constant over a series of compounds.View full abstractDownload PDF (1054K) -
Osamu Yamauchi, Hisashi Tanaka, Toyozo Uno1966 Volume 14 Issue 9 Pages 948-952
Published: September 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs part of the systematic studies on imidazole derivatives as chelating agents, four azoimidazoles having an ortho-hydroxy group, a dimethylamino group, or both groups were prepared from 4(5)-amino-5(4)-methylimidazole as a diazo component and 2-naphthol, p-methoxyphenol, N, N-dimethylaniline, and N, N-dimethyl-m-aminophenol as coupling components : 1-[4(5)-methyl-5(4)-imidazolylazo]-2-naphthol ; 2-[4(5)-methyl-5(4)-imidazolylazo]-4-methoxyphenol ; 4(5)-methyl-5(4)-(p-dimethylaminophenylazo) imidazole ; 3-dimethylamino-6-[4(5)-methyl-5(4)-imidazolylazo] phenol. The reactions of the azo derivatives with various metal ions were studied by spot tests in acid, neutral, and alkaline solutions. All the azo derivatives react with metal ions, such as Fe(III), Co(II), Ni(II), Cu(II), Zn(II), Pd(II) and Pb(II), to give intensely colored chelates which are usually extracted into chloroform or iso-amyl alcohol. These results indicate that the azoimidazoles can be used as metallochromic indicators or as extractants for determinations of metal ions by chelatometric titrations or by solvent extractions.View full abstractDownload PDF (594K) -
Osamu Yamauchi, Hisashi Tanaka, Toyozo Uno1966 Volume 14 Issue 9 Pages 952-958
Published: September 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSpectrophotometric and potentiometric investigations of the acid-base equilibria of the following azoimidazoles in aqueous media were carried out with a view to get some basic knowledge for their applications to chelatometric titrations as metallochromic indicators and for the calculations of the stability constants of their metal chelates : 1-[4(5)-methyl-5(4)-imidazolylazo]-2-naphthol ; 2-[4(5)-methyl-5(4)-imidazolylazo]-4-meth-oxyphenol; 4(5)-methyl-5(4)-(p-dimethylaminophenylazo) imidazole ; 3-dimethylamino-6-[4(5)-methyl-5(4)-imidazolylazo] phenol. pH Titrations of these azoimidazoles in 50v/v% dioxane-H2O at 25±0.1°afforded their acid dissociation constants (pKa). By comparing with the pKa values of 2-phenyl-azoimidazole (3.2) and 2-methyl-4(5)-phenylazoimidazole (4.5), assignments of the pKa values, pK<N__H>+(CH3)2, pK__(NH+), pK__(OH), and pK__(NH+), which refer to the pKa values of dimethyl-amino group, pyridine nitrogen, hydroxy group, and imino group, respectively, were attempted : pK<N__H>+(CH3)2< 2; pK__(NH)+=3.8∼5.1; pK__(OH)=11.0∼11.8; pK__(NH)>12. The pK__(NH+) of I and the pK<N__H>+(CH3)2, pk__(NH+), an dpK__(NH) of III were also obtained spectrophotometrically by plotting the absorbances of I (50 v/v% EtOH-H2O) and III (2 v/v% EtOH-H2O) against pH.View full abstractDownload PDF (696K) -
Shoji Kojima, Hisashi Ichibagase, Sadao Iguchi1966 Volume 14 Issue 9 Pages 959-965
Published: September 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSStudies on the absorption and excretion of CHS-Na in rabbit and human are reported in this paper. The urinary excretion rate of CHS-Na was determined after oral administration to rabbit, and the absorption rate was calculated from the excretion data. And the absorption of CHS-Na was studied after oral administration with the compounds such as caffeine, theophylline, theobromine, albumin, casein, and citric acid, and it was suggested that the absorption of CHS-Na was accelerated in the presence of caffeine and citric acid.View full abstractDownload PDF (691K) -
Shoji Kojima, Hisashi Ichibagase, Sadao Iguchi1966 Volume 14 Issue 9 Pages 965-971
Published: September 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe absorption of CHS-Na, saccharin, or dulcin from the stomach and the small intestine of the anesthetized rat was measured. CHS-Na was very poorly absorbed, while dulcin showed the greatest absorption rate. The absorpton of CHS-Na was considerably reduced in rat and rabbit anesthetized with pentobarbital . The same results were obtained in the absorption of tolazoline, but were not in that of salicylamide. These results suggest that the decreasing in the absorption of CHS-Na or tolazoline in situ depends mainly upon the anesthetic effect of pentobarbital. And the absorption of CHS-Na was measured in the presence of other compounds. The samll intestinal absorption of CHS-Na was measured in the presence of other compounds. The small intestinal absorption of CHS-Na was accelerated by the addition of caffeine or citric acid to it.View full abstractDownload PDF (749K) -
Shoji Kojima, Hisashi Ichibagase1966 Volume 14 Issue 9 Pages 971-974
Published: September 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe urinary metabolic product of CHS-Na in human, rabbit, and dog was studied. As a metabolite of CHS-Na, cyclohexylamine was found in the urine from human and dog which were received CHS-Na orally. From human urine, the metabolite was isolated as a benzoyl derivative and was quantitatively estimated. In rabbit, however, any metabolite of CHS-Na was not found in our experiment.View full abstractDownload PDF (544K) -
Tetsuji Kametani, Haruhiko Yagi, Shigeo Kaneda1966 Volume 14 Issue 9 Pages 974-980
Published: September 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSO-Benzylmagnolamine (XXI) was successfully obtained by the modified Ullmann reaction of dl-7-benzyloxy-1-(4, 5-bisbenzyloxy-2-bromobenzyl)-1, 2, 3, 4-tetrahydro-6-methoxy-2-methylisoquinoline (III) with 7-benzyloxy-1-(4-hydroxybenzyl)-1, 2, 3, 4-tetrahydro-6-methoxy-2-methylisoquinoline (IV) without any detectable side reaction in thin-layer chromatography. Since removal of benzyl group by hydrolysis had already afforded magnolamine (I), a modified total synthesis of stereoisomeric mixture of magnolamine has been accomplished.View full abstractDownload PDF (842K) -
Shoshiro Nakamura, Hamao Umezawa1966 Volume 14 Issue 9 Pages 981-986
Published: September 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBottromycin A2 is hydrolyzed to tetrapeptide and dipeptide by alkaline hydrolysis. The structures of both peptides are determined to be 3, 3-dimethyl-2-aminobutylylvalyl-3-methylprolylglycine and 3-methyl-3-phenylalanyl-3-(2-thiazolyl)-β-alanine. Hydrochloric acid hydrolysis of bottromycin A2 gives Δ1-isocaproyltetrapeptide and the structure is discussed on the bases of pKa studies. The structure of bottromycin A2 is proposed from the results above described.View full abstractDownload PDF (778K) -
Toshio Kinoshita, Morizo Ishidate, Zenzo Tamura1966 Volume 14 Issue 9 Pages 986-990
Published: September 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS3-Ketoglucuronic acid, a new 1, 3-dicarbonyl carbohydrate, was synthesized. 5-O-Acetyl-1, 2-O-isopropylidene-D-glucofuranurono-6, 3-lactone (I) was converted into methyl 5-O-acety-1, 2-O-isopropylidene-D-glucofuranuronate (IId), which was oxidized with chromium trioxide to give 3-keto-5-O-acetyl-1, 2-O-isopropylidene-D-glucofuranuronate (III). Ethyl acetate was found to be an excellent solvent for this oxidation. Removal of protective groups from III afforded crystalline 3-ketoglucuronic acid (VII). The intermediate substance (III) underwent stereo-selective reduction by the action of lithium aluminum hydride to produce 1, 2-O-isopropylidene-D-allofuranose.View full abstractDownload PDF (717K) -
Toshio Kinoshita, Morizo Ishidate, Zenzo Tamura1966 Volume 14 Issue 9 Pages 991-996
Published: September 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPeriodate oxidation of 3-ketoglucuronic acid indicated the presence of hemiacetal ring structure and in consequence the uronic acid was assigned as 3-keto-D-glucopy-ranuronic acid (III), which on treatment with cation resin in methanol gave methyl furanoside (V). Enolization of 3-ketoglucuronic acid between C-2 and C-3 was confirmed by conversion of the Keto-acid into the corresponding enol ether, namely methyl 3-O-methyl-D-glucopyranoenediol-(2, 3)-uronate (VIII). Equilibrium between keto-and enol from of this keto-sugar in an aqueous solution was, however, found to be inclined predominantly to the keto-form (III) by means of polarography.View full abstractDownload PDF (665K) -
Minoru Sekiya, Keiichi Ito1966 Volume 14 Issue 9 Pages 996-1006
Published: September 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHydrogenolysis of N-acylaminomethyl and additionally N-arylsulfonamidomethyl compounds attached to a variety of amines, not only under conditions with Raney nickel catalyst under high hydrogen pressure, but also, in some cases, under those with palladium-on-charcoal catalyst under ordinary hydrogen pressure, was investigated in a view of the factors affecting the rate. Solvent and variation in the structure were recognized to be major rate-determining factors. Comparison of the rates of a large number of the compounds indicates that the hydrogenolysis is more facilitated with increase of electron density at amine nitrogen and decrease of that at each acylamino and sulfonamido nitrogen. The reaction scope was established and the application in N-methylation of amine was generalized.View full abstractDownload PDF (1123K) -
Minoru Sekiya, Keiichi Ito1966 Volume 14 Issue 9 Pages 1007-1009
Published: September 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSN-Monomethylation of a variety of aromatic primary amines was successfully carried out through the hydrogenolysis of N-(arylaminomethyl) phthalimides. The method was quite general for rather basic aromatic primary amines, leading to good yield of the N-monomethylated amines.View full abstractDownload PDF (469K) -
Ikutoshi Matsuura, Fumio Yoneda, Yoshihiro Nitta1966 Volume 14 Issue 9 Pages 1010-1016
Published: September 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS8-Oxo-7, 8-dihydropyrido[2, 3-d]pyridazine-5-carboxylic acid, 7-phenyl-8-oxo-7, 8-dihydropyrido[2, 3-d]pyridazine-5-carboxylic acid, and their esters, amides and hydrazides were prepared. Alkaline hydrolysis of 7-phenyl-8-oxo-7, 8-dihydroprido[2, 3-d]pyridazine-5-carboxylates gave phenylhydrazone of 3-formylpicolinic acid and good yields of 3-(2-carbamoyl)pyridylglyoxylates. Reaction of quinolinic anhydride with 2 molar equivalents of phenylhydrazine in acetic acid gave the cyclized phenylhydrazide, and its structure, 5-hydroxy-7-phenylpyrido[2, 3-d]pyridazin-8(7H)-one, was determined by its chlorination followed by catalytic hydrogenation to give 7-phenyl-1, 2, 3, 4-tetrahydropyrido[2, 3-d]pyridazin-8(7H)-one. 6, 7-Diphenylpyrido[2, 3-d]pyridazine-5, 8(6H, 7H)-dione was also prepared.View full abstractDownload PDF (831K) -
Kenji Suzuki, Takashi Abiko1966 Volume 14 Issue 9 Pages 1017-1023
Published: September 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe synthesis of 6-β-alanine, 4-β-alanine, and 4, 6-di-β-alanine-bradykinin is described. The biological activity of three analogs were compared with that of bradykinin.View full abstractDownload PDF (1000K) -
Shoji Shibata, Isao Kitagawa, Haruhiro Fujimoto1966 Volume 14 Issue 9 Pages 1023-1033
Published: September 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA sapogenin, for which the name saikogenin A is proposed, has been obtained from saponins of Bupleurum falcatum L (Mishimasaiko). The present study has given the structural formula (I) for saikogenin A.View full abstractDownload PDF (1141K) -
Shojiro Uyeo, Hideaki Shirai, Akira Koshiro, Tamotsu Yashiro, Kengo Ka ...1966 Volume 14 Issue 9 Pages 1033-1039
Published: September 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS4-Acetoxy-7'-methoxyspiro[cyclohexane-1, 1' (2'H)-naphthalen]-4'(3'H)-one (XXIV) has been synthesized and subjected to the Schmidt reaction to give the isomeric benzaze-pinones (XXV and XXVI). N-methylation followed by reduction with lithium aluminum hydride of these compounds (XXV and XXVI) afforded the 1-and 2-benzazepine (II and III), respectively. In contrast to the inhibitory effect of galanthamine (I) on acetylcholinesterase, neither of these two synthetics showed appreciable anticholinesterase activity.View full abstractDownload PDF (882K) -
Hiroaki Nomura, Keiichi Sugimoto1966 Volume 14 Issue 9 Pages 1039-1044
Published: September 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBenzoylation of the enediol system of L-ascorbic acid and 5, 6-isopropylidene-L-ascorbic acid have been investigated with the aim of obtaining O-benzoyl derivatives of L-ascorbic acid stabilized against oxidation. 2-O-benzoyl-L-ascorbic acid, 3-O-benzoyl-5, 6-isopropylidene-L-ascorbic acid, 2, 6-di-O-benzoyl-L-ascorbic acid, 3, 6-di-O-benzoyl-L-ascorbic acid and 3, 5, 6-tri-O-benzoyl-L-ascorbic acid have been prepared by making choice of suitable reaction conditions, especially of the mole ratios of the three reagents i.e.L-ascorbic acid or its isopropylidene homologues, benzoyl chloride and base. The structure of the products were determined on the basis of elementary analyses. IR and NMR data supplemented by UV spectra and PK values.View full abstractDownload PDF (679K) -
Yoshio Imai1966 Volume 14 Issue 9 Pages 1045-1048
Published: September 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSome derivatives of L-ascorbic acid (L-AsA), including a monoester of the endiol group, were studied for their antiscorbutic activity in guinea pigs. Among them 2-O-benzoyl-L-AsA was found to have almost the same activity as that of L-AsA, i.e. even the oral dose equimolar to 1mg. of L-AsA/animal/day might be effective to prevent the development of scurvy. 2, 6-Di-O-benzoyl-L-AsA and 3, 5, 6-tri-O-benzoyl-L-AsA were shown to be less active antiscorbutically, may be one-tenth or below, than L-AsA.View full abstractDownload PDF (501K) -
Mieko Suzuki, Nobuo Ikekawa1966 Volume 14 Issue 9 Pages 1049-1051
Published: September 25, 1966
Released on J-STAGE: March 31, 2008
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Kunitoshi Yoshihira, Shinsaku Natori1966 Volume 14 Issue 9 Pages 1052-1053
Published: September 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDownload PDF (369K) -
Otohiko Tsuge, Masashi Tashiro, Ryuzo Mizuguchi, Shuji Kanemasa1966 Volume 14 Issue 9 Pages 1055-1057
Published: September 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDownload PDF (377K) -
Mikio Yamazaki, Mitsuyoshi Matsuo, Kiyohiko Arai1966 Volume 14 Issue 9 Pages 1058-1059
Published: September 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDownload PDF (354K) -
Zen-ichi Horii, Miyoji Hanaoka, Yasumitsu Tamura, Seiichi Saito, Norio ...1966 Volume 14 Issue 9 Pages 1059-1060
Published: September 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDownload PDF (324K)
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