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Volume 12, Issue 6
Displaying 1-24 of 24 articles from this issue
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Shunsaku Shiotani, Kemmotsu Mitsuhashi1964 Volume 12 Issue 6 Pages 647-651
Published: June 25, 1964
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe authors have attempted to synthesize a number of compounds belonging to the diazabenzobicyclo [3.3.1] nonane system shown by formula (I). Some derivatives of 3, 4, 5, 6-tetrahydro-2H-1, 5-methanobenzo [g] [1, 4] diazocine, e.g., 4-methyl-3, 4, 5, 6-tetrahydro-2H-1, 5-methanobenzo [g] [1, 4] diazocine (II a) and its 9-methoxyl derivative (II b), were synthesized, and their structures were confirmed by chemical as well as spectral methods.View full abstractDownload PDF (640K) -
Masakatsu Sakata, Masanobu Haga, Setsuzo Tejima, Masuo Akagi1964 Volume 12 Issue 6 Pages 652-656
Published: June 25, 1964
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWhen potassium alkyl- or benzylxanthate was reacted on acetylated D-glucopyranosyl halides in ethanol or in acetone, acetylated D-glucopyranosyl xanthates, acetylated di-D-glucopyranosyl sulfides, and acetylated β-D-thioglucosides formed. The yield of each condensation products was affected by choice of solvent, the reaction temperature, the potassium xanthate, and starting halide used. A simple method for the preparation of bis (2, 2', 3, 3', 4, 4', 6, 6'-octa-O-acetyl-β, β'-D-glucopyranosyl) sulfide (octa-O-acetyl-isothiotrehalose) was confirmed by the reaction of potassium methyl- or benzylxanthate upon 2, 3, 4, 6-tetra-O-acetyl-α-D-glucopyranosyl bromide. Two other isomers of octa-O-acetyl-isothiotrehalose were synthesized as crystalline forms.View full abstractDownload PDF (717K) -
Kazuo Yoshida, Keitaro Kato, Hisao Tsukamoto1964 Volume 12 Issue 6 Pages 656-663
Published: June 25, 1964
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1. The glucuronyl transfer reaction from ester glucuronides to aliphatic alcohols were examined with partially purified rabbit liver β-glucuronidase and E. coli β-glucuronidase. The enzymes transferred the glucuronic acid moiety of ester glucuronides to aliphatic alcohols. The product with methanol was identified to be methyl glucuronide by paper chromatography. The product was completely hydrolyzable by β-glucuronidase, proving it to be a β-glucosiduronic acid of methanol. 2. The glucuronyl transfer from ester glucuronides to m-aminophenol was examined. The product formed by glucuronyl transfer from benzoyl β-D-glucuronide to m-aminophenol was purified with ion exchange resin. It contained equimolar amounts of m-aminophenol and glucuronic acid. The paper electrophoretic and paper chromatographic behavior of this purified product was presented. In paper chromatography, the Rf value of this product was different from that of authentic m-aminophenyl β-D-glucuronide. This product was not hydrolyzable by β-glucuronidase and more stable in acidic milieu than authentic m-aminophenyl β-D-glucuronide. These facts suggested the presence of α-glucosiduronic linkage in its molecule.View full abstractDownload PDF (902K) -
Keitaro Kato, Kazuo Yoshida, Hisao Tsukamoto1964 Volume 12 Issue 6 Pages 664-669
Published: June 25, 1964
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1. 2-Naphthyl β-D-grucofuranoside was synthesized from 2-naphthyl diacetyl-β-D-glucofuranosiduronolactone with lithium aluminum hydride, and the ring structure of this compound was examined by periodate oxidation. 2. Catalytic oxidation of 2-naphthyl β-D-glucofuranoside with gaseous oxygen and platinum black yielded 2-naphthyl β-D-glucofuranosiduronic acid. The ring structure of this compound was examined by periodate oxidation. Methyl 2-naphthyl β-D-glucofuranosiduronate was easily converted to 2-naphthyl β-D-glucofuranosiduronolactone. Methylation and acetylation of 2-naphthyl β-D-glucofuranosiduronic acid yielded 2-naphthyl diacetyl-β-D-glucofuranosiduronolactone.View full abstractDownload PDF (677K) -
Keitaro Kato, Kazuo Yoshida, Hisao Tsukamoto1964 Volume 12 Issue 6 Pages 670-674
Published: June 25, 1964
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2. The kinetics of the hydrolysis of 2-naphthyl β-D-glucofuranosiduronic acid by β-glucuronidase were investigated. The pH optimum of the β-D-glucofuranosiduronic acid is 5.0 in phosphate-citrate buffer at 38°. The reaction velocity is constant with time. The Michaelis-Menten constant is 1.75×10-2M. The kinetics of the hydrolysis of 2-naphthyl β-D-glucopyranosiduronic acid by the enzyme were also investigated. The pH optimum is 4.7. The Michaelis-Menten constant is 1.3×10-3M. 3. In view of the above facts, it was concluded that β-D-glucofuranosiduronic acids could be a substrate for β-glucuronidase.View full abstractDownload PDF (577K) -
Minoru Sekiya, Keiichi Ito, Minako Saito1964 Volume 12 Issue 6 Pages 674-677
Published: June 25, 1964
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1-Acylaminoarylmethylation of ethyl malonate was effected in several cases by interaction of N-arylmethylene-1-acylamino-1-arylmethylamine in refluxing toluene solution with suspended sodium hydroxide powder. Ethyl cyanoacetate, phenylacetonitrile and malononitrile formed arylmethylene derivatives under the same condition as with ethyl malonate.View full abstractDownload PDF (583K) -
Minoru Sekiya, Keiichi Ito1964 Volume 12 Issue 6 Pages 677-682
Published: June 25, 1964
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA number of N-acylaminomethyl and N-sulfonamidomethyl compounds were subjected to formic acid reduction using trimethylammonium formate as a reducing agent. The reduction was found to lead to a fission of the carbon bond connecting to the amide nitrogen. Ease of the reduction increased with lowering the electron density of the amide nitrogen. The compounds attached to aliphatic amine underwent the reduction almost quantitatively and, on the other hand, the aromatic amine homologs were less reactive. A possible mechanism for the reduction was proposed.View full abstractDownload PDF (805K) -
Akira Yokoyama, Hisashi Tanaka1964 Volume 12 Issue 6 Pages 683-689
Published: June 25, 1964
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEsters of β-mercaptothiocinnamic acid were prepared as strong chelating agents. Phenylpropioloyl chloride was converted into alkyl or aryl phenylthiopropiolate and thiourea was reacted in the presence of p-toluenesulfonic acid to obtain corresponding isothiuronium salts. Esters of β-mercaptothiocinnamic acid were obtained by the hydrolyses of the isothiuronium salts. Thioxo-thioenol tautomerism in the esters of β-mercaptothiocinnamic acid was investigated by infrared and nuclear magnetic resonance spectroscopy. It was found that cis-thioenol form is predominant and hence the mercapto group and the carbonyl group are markedly hydrogen-bonded.View full abstractDownload PDF (856K) -
Akira Yokoyama, Kazuo Ashida, Hisashi Tanaka1964 Volume 12 Issue 6 Pages 690-695
Published: June 25, 1964
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSβ-Mercaptocinnamamides were prepared as strong chelating agents. Phenylpropioloyl chloride was converted into alkyl- or arylamides, and thiourea was reacted in the presence of p-toluenesulfonic acid to obtain corresponding isothiuronium salts. β-Mercaptocinnamamides were obtained by the hydrolyses of the isothiuronium salts. Thioxo-thioenol tautomerism in the β-mercaptocinnamamides was investigated by infrared and nuclear magnetic resonance spectroscopy. It was found that cis-thioenol form is predominant in these amides but some differences were observed between alkylamides and arylamides. The arylamides were considered to have stronger chelating abilities than the alkylamides judging from their chemical properties, and this difference would be attributed to the difference in thioxo-thioenol tautomerism.View full abstractDownload PDF (696K) -
Junji Koizumi, Shigeru Kobayashi, Shojiro Uyeo1964 Volume 12 Issue 6 Pages 696-705
Published: June 25, 1964
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of galanthaminone with hydriodic acid gave hydroxyapogalanthamine, the structure of which has been elucidated by degradation to the known diphenic acid (IV). The trimethyl ether of hydroxyapogalanthamine has been synthesized by two methods, confirming the structure of this important transformation product of galanthaminone. Based on this and other chemical evidence it has been concluded that galanthamine is represented by formula (III).View full abstractDownload PDF (1518K) -
Ryoji Sawamura, Takashi Koyama1964 Volume 12 Issue 6 Pages 706-709
Published: June 25, 1964
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFluorescence was observed in the reaction of pentose with anthrone in strong sulfuric acid. The range of its fluorescence spectrum was from 470 to 600 mμ and the maximum was at about 510 mμ. The anthrone reagent itself had a flat fluorescence spectrum from 420 to 600 mμ for it contains anthranol, but the shape of its spectrum was quite different from pentose fluorescence, and, furthermore, the intensity was far weaker than pentose fluorescence. In the case of glucose the fluorescence spectrum resembled that of the blank. This reaction was specific for pentose in the presence of hexose, but excess glucose decreased the pentose fluorescence.View full abstractDownload PDF (528K) -
Kyosuke Tsuda, Yoshihiro Sato, Sayoko Tanaka, Hideaki Higashikuze, Nob ...1964 Volume 12 Issue 6 Pages 710-713
Published: June 25, 1964
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe microanalysis of human bile acids by gas liquid chromatography using 3/4% SE-52 packing is discussed. Bile acid ratios of lithocholic, deoxycholic, chenodeoxycholic and cholic acid in gallbladder bile were estimated.View full abstractDownload PDF (512K) -
Hirotaka Otomasu, Hiroshi Takahashi, Michihiko Ogata1964 Volume 12 Issue 6 Pages 714-717
Published: June 25, 1964
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe dipole moments of some pyrimidine, pyridazine, and their N-oxides (I to VIII) were measured in benzene solution at 25°. In alkoxy derivatives, the moments of two forms, cis and trans were considered by the bending structure of alkoxyl group, and the respective vectorical sums were calculated. Alkoxydiazines whose respective alkoxyl group is attached to the neighboring position of nitrogen atom showed all to exist as cis form. By the steric hindrance of cis form, in the alkoxy-diazine mono N-oxide the oxygen atom was postulated to attach to the nitrogen atom distant from the alkoxyl group.View full abstractDownload PDF (587K) -
Kentaro Okumura, Ichizo Inoue1964 Volume 12 Issue 6 Pages 718-724
Published: June 25, 1964
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs a part of studies on antipyretic-analgesic, the 1-phenyl-3-dialkylamino-2-pyrrolidinones and their 5-methyl analogs, including each diastereoisomeres, were synthesized.View full abstractDownload PDF (895K) -
Kentaro Okumura, Keishi Kotera, Ichizo Inoue1964 Volume 12 Issue 6 Pages 725-730
Published: June 25, 1964
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reductions of 1-phenyl-3-hydroxyimino-5-methyl-2-pyrrolidinone, using i) Platinum dioxide in glacial acetic acid, ii) Raney nickel in Ethanol, and iii) Aluminum mercury in moist tetrahydrofuran, were carried out to furnish two isomeric amines, designated as IIa and 1-phenyl-3-amino-5-methyl-2-pyrrolidinone (IIb). Quantitative ratios of these amines formed as regard to the reduction methods allowed us to assign cis-configuration to IIb and trans-configuration to IIa. From the studies of ultraviolet and nuclear magnetic resonance spectra of the 3-hydroxy-compounds, 1-phenyl-3-hydroxy-5-methyl-2-pyrrolidinone (IIIa) and 1-phenyl-3-hydroxy-5-methyl-2-pyrrolidinone (IIIb), prepared from IIa and IIb respectively, the occurrence of Walden-inversion in the diazotization reaction was concluded. At the same time cis-configuration of IIb and IIIa was also predicted, which was supported by leading IIIa to cis-1-tosyl-2-methyl-4-methoxypyrrolidine (X) synthesized from dl-allo-hydroxyproline.View full abstractDownload PDF (729K) -
Hisao Tsukamoto, Keitaro Kato, Kazuo Yoshida1964 Volume 12 Issue 6 Pages 731-734
Published: June 25, 1964
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1. The ester glucuronide of p-aminosalicylic acid was isolated from the urine of rabbits administered with p-aminosalicylic acid. The methyl acetyl derivative of this compound was identified with synthetic methyl (2-acetoxybenzoyl-4-acetamido-2, 3, 4-tri-O-acetyl-β-D-glucopyranosid) uronate. 2. The ester glucuronide of salicylic acid was isolated as methyl (2-acetoxybenzoyl-2, 3, 4-tri-O-acetyl-β-D-glucopyranosid) uronate from the urine of rabbits administered with salicylic acid, and the structure was confirmed with the synthetic compound.View full abstractDownload PDF (633K) -
Hisao Tsukamoto, Keitaro Kato, Kazuo Yoshida, Kiyoshi Tatsumi1964 Volume 12 Issue 6 Pages 734-737
Published: June 25, 1964
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1. UDP-transglucuronylase catalyzed the transfer of the glucuronyl group from UDP glucuronic acid to phenolic compounds, such as 2-naphthol, p-cresol, p-nitrophenol, m-aminophenol, and p-aminosalicylic acid, but the glucuronyl transfer by β-glucuronidase from phenolphthalein β-D-glucuronide or p-nitrophenyl β-D-glucuronide to these phenolic compounds was not observed. 2. The transfer product by β-glucuronidase from p-nitrophenyl β-D-glucuronide to methanol was identified by paper chromatography, and percentage of glucuronyl transfer activity was also measured. This glucuronide transferred 24.2 per cent of the liberated glucuronic group to methanol.View full abstractDownload PDF (624K) -
Hiroshi Morimoto, Isuke Imada1964 Volume 12 Issue 6 Pages 739-741
Published: June 25, 1964
Released on J-STAGE: March 31, 2008
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Morio Ikehara, Hitoshi Uno1964 Volume 12 Issue 6 Pages 742-744
Published: June 25, 1964
Released on J-STAGE: March 31, 2008
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Tadashi Miyasaka1964 Volume 12 Issue 6 Pages 744-747
Published: June 25, 1964
Released on J-STAGE: March 31, 2008
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Isamu Murakoshi, Akinori Kubo, Junichi Saito, Joju Haginiwa1964 Volume 12 Issue 6 Pages 747-749
Published: June 25, 1964
Released on J-STAGE: March 31, 2008
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Yasuo Inubushi, Yoshisuke Tsuda, Takeshi Konita, Saichi Matsumoto1964 Volume 12 Issue 6 Pages 749-750
Published: June 25, 1964
Released on J-STAGE: March 31, 2008
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Masayuki Onda, Hiroshi Fukushima, Masuko Akagawa1964 Volume 12 Issue 6 Pages 751
Published: June 25, 1964
Released on J-STAGE: March 31, 2008
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Takayuki Wada, Daisuke Satoh1964 Volume 12 Issue 6 Pages 752-753
Published: June 25, 1964
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDownload PDF (518K)
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