Chemical and Pharmaceutical Bulletin

Studies on the Sulfurcontaining Chelating Agents. XI. Relationship between Chelating Ability and Chemical Structure of Ligand.(1)

Hisashi Tanaka, Akira Yokoyama

1962 Volume 10 Issue 12 Pages 1129-1133
Published: December 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1129

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Stabilities of copper, palladium, nickel, cobalt and iron chelates of various types of ligands involving mercapto and carbonyl groups was compared with each other qualitatively, and “Irving and Williams' stability series” was found to be applicable to these chelates. Apparent stability constants of these chelates were determined. From the results of these experiments, relationship between chelating abilities and chemical structures of the ligands were investigated.

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Studies on the Sulfurcontaining Chelating Agents. XII. Relationship between Chelating Ability and Chemical Structure of Ligand.(2)

Hisashi Tanaka, Akira Yokoyama

1962 Volume 10 Issue 12 Pages 1133-1137
Published: December 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1133

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Stabilities of copper, palladium, nickel, cobalt, and iron chelates of various tyres of ligands involving the mercapto and the carbonyl group were compared each other by measuring the pH at 50% extractability of the chelates into chloroform and at incipient chelate formation. From the results of these experiments, relationship between chelating abilities and chemical structures of the ligands was confirmed. The ligands which involve conjugated double bond in their chelate ring and those involve thiolic acid ester group were found to have stronger chelating ability.

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A Synthesis of 2'-Acetyl-5, 5', 6-trimethoxy-2-biphenylcarboxylic Acid

Shigeru Kobayashi, Chizuru Kuraishi

1962 Volume 10 Issue 12 Pages 1137-1141
Published: December 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1137

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It has been found that the Friedel-Crafts reaction of 3-iodoanisole with acetyl chloride yielded, contrary to Oki's report, four products, 2'-hydroxy-4'-iodo-, 2'-iodo-4'-hydroxy, 2'-iodo-4'-methoxy-, and 2'-methoxy-4'-iodoacetophenone
The Ullmann condensation of 2'-iodo-4'-methoxyacetophenone with methyl 2-bromoor2-iodo-veratrate, followed by hydrolysis, gave, in a poor yield, 2'-acetyl-5, 5'6-trimethoxy-2-biphenylcarboxylic acid which was characterized as its oxime as well as its methyl ester.

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Potential Anti-Cancer Agents. VII. Azido-purine Derivatives

Takanobu Itai, Genzo Ito

1962 Volume 10 Issue 12 Pages 1141-1145
Published: December 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1141

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Azido derivatives of 7-methylpurine were synthesized from 2, 6-dichloro-7-methylpurine (I) and 2, 6, 8-trichloro-7-methylpurine (II), and they were catalytically reduced to corresponding amino derivatives. From the results, it might be thought that the azido groups on purines existed as -N=N⁺=N^- and did not form tetrazole ring.

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Studies on Acylase Activity and Microorganisms. XIX Optical Resolution of Threonine, Lysine, Tryptophan, and Methionine by Acylase of Soil Bacteria

Yukio Kameda, Katsuhiko Matsui, Yukio Kimura, Etsuko Toyoura, Masako K ...

1962 Volume 10 Issue 12 Pages 1146-1151
Published: December 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1146

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Fifteen strains (KT 202, KT 205, KT 207, etc.) of soil bacteria capable of asymmetric hydrolysis of N-benzoyl-DL-threonine, 2, 6-di-N-benzoyl-DL-lysine, N-acetyl-DLlysine, N-acetyl-DL-tryptophan or N-acetyl-DL-methionine were isolated by using a synthetic medium containing N-acyl-derivatives of amino acids as the sole source of carbon (Table I).
N-Benzoyl-DL-threonine was asymmetrically hydrolyzed to L-threonine, N-benzoyl-D-threonine and benzoic acid by the acylase of KT 218, KT 229, and KT 83, while 2, 6-di-N-benzoyl-DL-lysine, to 6-N-benzoyl-L-lysine, 2, 6-di-N-benzoyl-D-lysine and benzoic acid by KT 218 and KT 229.
KT 241 and KT 224 hydrolyzed asymmetrically N- acetyl- DL-tryptophan and N-acetyl-DL-methionine to L-tryptophan and N-acetyl-D-tryptophan, and L-methionine and N-acetyl-D-methionine, respectively.
It was observed that N-acetyl-D-tryptophan and N-acetyl-D-methionine were hydrolyzed by several strains (KT 229, KT 83, KT 222, etc.) of soil bacteria.
It seems of interest to note that N-acetyl-L-methionine was more easily hydrolyzed by KT 224 or KT 218 than N-acetyl-L-tryptophan, while the latter was more easily hydrolyzed by KT 241, and that the N-acetyl derivative of L-methionine was more easily hydrolyzed by KT 224 or KT 241 than the N-benzoyl derivative, while the latter was more easily hydrolyzed by KT 218.

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Studies on Acylase Activity and Microorganisms. XX. Isolation of Soil Bacteria Capable of Resolving Tryptophan by their Acylase on N-Acetyl-DL-tryptophan

Yukio Kameda, Yoshiko Ishii

1962 Volume 10 Issue 12 Pages 1152-1153
Published: December 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1152

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Two strains (KT 251 and KT 253) of bacteria capable of resolving tryptophan by their acylase on N-acetyl-DL-tryptophan were isolated from soil samples by using a synthetic medium containing N-acetyl-DL-tryptophan as the sole source of carbon. Both. KT 251 and KT 253 could be cultivated in various synthetic media.

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Studies on Acylase Activity and Microorganisms. XXI. Optical Resolution of Higher Amino Acids by Acylase of Soil Bacteria

Yukio Kimura

1962 Volume 10 Issue 12 Pages 1154-1157
Published: December 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1154

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The acylase activity of a strain (KT 218) of soil bacteria was tested against N-benzoyl and N-dichloroacetyl derivatives of 2-aminooctanoic, 2-aminodecanoic, 2-aminolauric, 2-aminomyristic, and 2-aminopalmitic acid. It was revealed that the dichloroacetylaminoacids were more easily hydrolyzed than the corresponding benzoylamino acids and that the N-dichloroacetyl-derivatives of the homologous series of straight chain 2-aminoacid were hydrolyzed at progressively decreasing rates from N-dichloroacetyl-DL-2-aminooctanoic acid to N-dichloroacetyl-DL-2-aminopalmitic acid which was resistant to KT 218 acylase.
The acetone powder of KT 218 effected asymmetric hydrolysis of N-dichloroacetyl derivatives of 2-aminooctanoic, 2-aminodecanoic, 2-aminolauric, 2-aminomyristic acids to yield respectively L-2-aminooctanoic acid (XI) and N-dichloroacetyl-D-2-aminooctanoic acid (XV), L-2-aminodecanoic acid (XII) and N-dichloroacetyl-D-2-aminodecanoic acid (XVI), L-2-aminolauric acid (XIII) and N-dichloroacetyl-D-2-aminolauric acid (XVII), and L-2-aminomyristic acid (XIV) and impure N-dichloroacetyl-D-2-aminomyristic acid. In the same way KT 218 acetone powder effected asymmetric hydrolysis of N-benzoyl derivatives of 2-aminooctanoic, 2-aminodecanoic, and 2-aminolauric acids to yield respectively L-2-aminooctanoic acid (XI) and N-benzoyl-D-2-aminooctanoic acid (XVIII), L-2-aminodecanoic acid (XII) and impure N-benzoyl-D-2-aminodecanoic acid, and L-2-aminolauric acid (XIII) and impure N-benzoyl-D-2-aminolauric acid.

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Studies on Decomposition and Stabilization of Drugs in Solution. XII. Stabilization of Methantheline Bromide in Aqueous Solution by Surface-active Agents.(2)

Hisashi Nogami, Shoji Awazu

1962 Volume 10 Issue 12 Pages 1158-1160
Published: December 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1158

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Sodium laurylsulfate, an anionic surfactant, promoted the H⁺ catalysed hydrolysis of methantheline bromide, quaternary amine ester. This contrasts with the phenomenon that sodium laurylsulfate suppressed the OH^- catalysed hydrolysis of methantheline bromide. This difference may be explained with the attraction and repulsion between the electric charges of the sodium laurylsulfate micelle and those of catalytic species.

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Studies on Absorption and Excretion of Drugs. III. Kinetics of Penetration of Sulfonamides through the Intestinal Barrier in Vitro

Hisashi Nogami, Manabu Hanano, Jun Watanabe

1962 Volume 10 Issue 12 Pages 1161-1167
Published: December 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1161

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1. The penetration ofsulfonamides through the rat small intestine was investigated from the physicochemical standpoint in vitro.
2. Theoretical equations for the penetration mechanism of sulfathiazole were derived from the assumption that it penetrates through intestinal barrier in its three forms at the respective penetration rates.
3. From the data obtained, the respective permeability coefficients for the undissociated, alkaline and acid forms of sulfathiazole, P₁, P₂, and P₃ were statistically determined. The estimated values of P¹, P₂, and P₃ were 0.00064, 0.00979, 0.00132 (cc./cm./min.), respectively.
4. The experiment at the equilibrium state was attempted in order to examine the validity of the theoretical equation. Satisfactory results are obtained for P₁ and P₃, but not for P₂.
5. The penetration rates of fivesulfonamides were compared at the same pH value. The penetration rates were in the following order: sulfisomezole>sulfamethoxypyridazine<sulfanilamide<sulfathiazole<sulfaguanidine.

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Synthesis and Antiviral Effect of Hexahydro-s-triazines

Takeo Ueda, Shigeshi Toyoshima, Tadakazu Tsuji, Sumiko Watanabe

1962 Volume 10 Issue 12 Pages 1167-1172
Published: December 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1167

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The condensation of guanidine nitrate with acetaldehyde-ammonia furnished 2-imino-4, 6-dimethylhexahydro-s-triazine nitrate. 2-Imino- 5-methylhexahydro-s-triazine nitrate was also prepared by the same way.
The alkyl derivatives of tetrahydro-s-triazine-2 (1H)-thione and tetrahydro-s-triazin-2 (1H)-one were synthesized by the condensation of either thiourea or urea with amine and aldehyde.
These compounds were screened as to their inhibitory effect on poliomyelitis virus by tissue culture method. Only 2-Imino-4, 6-dimethylhexahydro-s-triazine nitrate, among the compounds screened, showed an effect, and it exerted fairly an inhibitory effect on the type-1 and -2 strains of poliomyelitis virus, but it has not so significant effect on the type-3 strain. Moreover, this compound was found to inhibit a multiplication of the Edmonstan strain of measles virus, although its effect was not so significant.

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Bile Acids and Steroids. XXII. Thiosteroids.(7). Synthesis of Some Thiazolo [5', 4'-16, 17] steroids by the Hantzsh Reactions

Ken'ichi Takeda, Taichiro Komeno

1962 Volume 10 Issue 12 Pages 1173-1177
Published: December 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1173

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2'-Methylthiazolo [5', 4'-16.17] androsta-15, 16-dien-3β-o1 (VII) was prepared by an established method from 3β-acetoxy-16β-bromoandrost-5-en-17-one (VI) and thioacetamide. Consequently the aromatic compound (IV) which was obtained by dehydration of the by-product (III) of the Beckmann rearrangement of the oxime-mixture (Ia) and (Ib) of 3β-acetoxy-17α-hydroxy-16β-thiocyanatopregn-5-en-20-one and which was assigned an uncorrect thiazol structure (VII) in the previous paper, should be 3'-methylisothiazolo [5', 16, 17] androsta-5, 16-dien-3β-o1 acetate. 2'-Amino-16, 17-disubstituted thiazolo-compound was also prepared from (VI) and thiourea.

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Steroid Series. IX.A New Route to 6-Nitrosteroid Derivatives

Katsumi Tanabe, Ryozo Hayashi

1962 Volume 10 Issue 12 Pages 1177-1183
Published: December 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1177

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Treatment of cholesterol acetate (Ia), androst-5-ene-3β, 17β-diol diacetate (Ib), and 3β-hydroxyalndrost-5-en-17-one acetate (Ic) with nitrosyl chloride afforded the corresponding 5α-chloro-6β-nitro compound in high yield. The adduct could be converted readily to a Δ⁵-6-nitro compound on treatment under basic conditions and also into a Δ⁴-3-oxo-6α-nitrosteroid derivative.

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Medical and Biochemical Application of Infrared Spectroscopy. VI.Studies on Human Bile by Infrared Spectra and Some of its Clinical Application

Goro Chihara, Kimiko Matsuo, Kimiko Shirakuma, Ayako Mizushima, Emiko ...

1962 Volume 10 Issue 12 Pages 1184-1189
Published: December 25, 1962
Released on J-STAGE: May 27, 2011

DOIhttps://doi.org/10.1248/cpb.10.1184

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Infrared spectral measurement was introduced into the analysis of bile and this was proved to be the new, simple, and effective tool for clinical tests.
1) Interpretation of the infrared spectrum of dried whole bile was established and a method was revealed for finding quantitative difference of various components of bile from its absorptions. Some examples of clinical application for the detection of abnormal bile was described.
2) Bile acids, bile pigments, bile lipids, and mucoic substances were separated from bile by a simple procedure and the method was revealed to find quantitative changes in the components constituting each of these fractions from their infrared spectra.
3) This infrared spectral analysis was found to be a new and simple method for finding the kind of bile acids present, which had been difficult by the known methods. It was found that the main component of bile acids in normal human bile is cholic acid and not deoxycholic acid.

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Medical and Biochemical Application of Infrared Spectroscopy. VII. Studies on Various Animal Bile by Infrared Spectra and Some of its Pharmaceutical Application, Including Identification of the Bear Bile (Yutan)

Goro Chihara, Kimiko Matsuo, Kimiko Shirakuma, Kumiko Arimoto, Shigeko ...

1962 Volume 10 Issue 12 Pages 1190-1195
Published: December 25, 1962
Released on J-STAGE: May 27, 2011

DOIhttps://doi.org/10.1248/cpb.10.1190

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A large number of bile from 18 kinds of animals were submitted to infrared spectral measurement and it was revealed that these spectra were very effective in knowing various bile components and constituents of bile acids. This method was successfully utilized in discriminating Yiatan (bear bile), used as the valuable home remedy in the Orient from olden times, from the bile of other animals.
Some results different from past reports were obtained; notably that the main component of carp bile is not bile acid but is a sulfate of bile alcohol and that the conjugate amino acid in the bile acids of some fish was not taurin.
Infrared spectra of bile from about 100 dogs were examined as basis for the study of pharmacological action of choleretics. Infrared spectrum of dog bile is especially distinct, there is no necessity of considering individual differences, and there are no variation in the amount of bile outflow or infrared spectrum even eight hours after the operation.

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Studies on the Steroidal Components of Domestic Plants. XL. Constituents of Heloniopsis orientalis (T_HUNB.) C. T_ANAKA.(3) The Structure of Heloniogenin

Tameto Okanishi, Akira Akahori, Fumio Yasuda

1962 Volume 10 Issue 12 Pages 1195-1199
Published: December 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1195

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A new steroidal sapogenin isolated from Heloniopsis orientalis (THUNB.) C. TANAKA was named “heloniogenin”. The chromic acid oxidation of this sapogenin yielded gentrogenin. Gentrogenin acetate was also obtained with the chromic acid oxidation heloniogenin 3-acetate. Of two isomers derived from gentrogenin with the metal hydride reduction, 3β, 12α-diol was identified with heloniogenin. The structure of heloniogenin was confirmed as 25D-spirost-5-ene-3β, 12α-diol.

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Infrared Spectra of Thiourea and its Inclusion Compounds. I. Vibrational Spectrum of Rhombohedral Thiourea

Masao Nishikawa, Hiroyuki Mima, Tokunosuke Kanzawa

1962 Volume 10 Issue 12 Pages 1199-1204
Published: December 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1199

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Infrared spectra of thiourea and its adducts were determined in the region between 4000 and 400cm^-1 with a high resolution spectrophotometer. The spectra of adducts were almost similar. Through an investigation with polarized light on orientated thin crystals of adducts, nearly all fundamental bands were assigned. The assignments were also performed to the absorption bands of deuterated thiourea and its inclusion compound with decaline.
The results were examined with the product rule, the agreement being fairly good. Considerable changes were observed in NH stretching vibrations and wagging one, which showed strengthening of the intermolecular hydrogen bonds. The energy gain owing to this change would stabilize the adduct crystal.

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Infrared Spectra of Thiourea and its Inclusion Compounds. II. Spectra of Guest Molecules

Masao Nishikawa

1962 Volume 10 Issue 12 Pages 1205-1211
Published: December 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1205

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The infrared dichroismic behaviors of molecules enclosed in a thiourea channel were investigated with an infrared microscope by using oriented single crystals of adducts. The absorptions of guest molecules in the region between 3000 and 1650cm^-1, 1590 and 1500cm^-1, and 1050 and 730cm^-1 were found to be measurable with this technique. The vibrational species of some of these absorptions were determined, especially in case of trans-and cis-decalins. Molecules having carboxylic group were revealed to form dimers as in solutions when they were included in a thiourea channel. This technique would be used to study dichroism of some kinds of organic molecules under certain limitation. Environmental effect exerted by thiourea cage has been also estimated. The results showed that it is comparable with that of solvents of dielectric constant 2.5-5.5.

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Studies on Biogenesis of Tea Components. III. The Origin of the Methyl Groups in Caffeine

Takao Inoue, Fumiko Adachi

1962 Volume 10 Issue 12 Pages 1212-1214
Published: December 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1212

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By feeding tea shoots with methionine-(methyl-¹⁴C) it was proved that the methyl group of methionine served as a precursor of the methyl groups of caffeine in tea plants.

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Reaction of 1-Arylbiguanide with Some Carboxylic Esters

Mitsuru Furukawa

1962 Volume 10 Issue 12 Pages 1215-1220
Published: December 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1215

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The reaction of arylbiguanide with carboxylic esters having a reactive functional group except the ester group such as ethyl cyanoacetate, ethyl acetoacetate and diethyl oxalate was attempted. Roy et al. inferred that the reaction product of arylbiguanide with ethyl cyanoacetate should be 2-arylguanidino-6-amino-4-pyrimidinol. Contrary to the Roy's result, however, the author proved that it might be 4-amino-6-arylamino-striazine-2-acetonitrile. In comparison with this fact, the reaction of 1-arylbiguanide with ethyl acetoacetate was confirmed to afford 2-arylguanidino-6-methyl-4-pyrimidinol under the similar reaction condition. Furthormore, the author defined the reaction mechanism in which 1-arylbiguanide reacts with diethyl oxalate to give ethyl 4-amino-6-arylamino-s-triazine-2-carboxylate through the intermediate formation of 1-aryl-3-(4, 5-dioxo-2-imidazolidinylidene)-guanidine. In connection with this finding, 4-amino-6-(p-toluidino)-s-triazine-2-carboxamide derivatives was found to be formed by the reaction of 1-(p-tolyl)-3-(4, 5-dioxo-2-imidazolidinylidene)-guanidine with corresponding amine. Therefore it is recommended to be a new method of synthesizing 4-amino-6-arylamino-s-triazine-2-carboxamides from 1-arylbiguanide, diethyl oxalate and an amine.

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Reduction of 4-Nitroquinoline 1-Oxide by Microörganisms

Tadashi Okabayashi, Akihiro Yoshimoto

1962 Volume 10 Issue 12 Pages 1221-1226
Published: December 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1221

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The ultraviolet absorption maximum of 4-nitroquinoline 1-oxide was shifted toward shorter wave length when the substance was added to the growing media of microorganisms. The investigation of this phenomenon revealed that the shift in ultraviolet absorption maxima is due to the reduction of nitro group at 4-position. It was also foundthat the reduction of N→Obond in 1-position occurs to a smaller extent.

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Studies on the Synthesis of New Antimicrobials. I. Synthesis of 2, 5-Dichloroaniline Derivatives and their Some Antibacterial Activities

Ryuichi Kimura, Takahiro Yabuuchi, Masakatsu Hisaki, Hideki Sugimoto, ...

1962 Volume 10 Issue 12 Pages 1226-1232
Published: December 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1226

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Twentyfour of new N-derivatives of 2, 5-dichloroaniline, 2, 5-dichloro-4-bromo-aniline and 2, 5-dichloro-4-thiocyanatoaniline were synthesized in order to investigate the potential antimicrobial activity. Among them, 2-hydroxy-5-bromobenzoyl derivatives were found to give strong antibacterial activities on Staph. aureus in vitro.

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Studies on the Synthesis of New Antimicrobials. II. Syntheses of 3-(5-Nitro-2-thienyl) acrylic Acid Derivatives and their Some Antibacterial Activities

Ryuichi Kimura, Takahiro Yabuuchi, Masakatsu Hisaki

1962 Volume 10 Issue 12 Pages 1232-1237
Published: December 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1232

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3-(5-Nitro-2-thienyl) acrylic acid was synthesized in good yield by direct nitration of 3-(2-thienyl) acrylic acid obtained from 2-thiophenecarboxaldehyde without proceeding through 5-nitro-2-thiophenecarboxaldehyde diacetate. By condensation of the acid with various amines, alcohols or phenols, its amide and ester derivatives were prepared. 2-Bromo-3-(5-nitro-2-thienyl) acrylic acid esters were also obtained by bromination of the corresponding esters.
Antibacterial activity of these compounds was tested on some bacteria in vitro.

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Metabolism of Drugs. XXXIII. Studies on the Ring Structure of p-Aminobenzoyl Glucuronide isolated from the Urine of Dog administered with p-Aminobenzoic Acid.(1)

Keitaro Kato, Kazuo Yoshida, Kiyoshi Tatsumi, Hisao Tsukamoto

1962 Volume 10 Issue 12 Pages 1238-1242
Published: December 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1238

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1. The ring structure of p-aminobenzoyl glucuronide isolated from the dog urine was confirmed through the synthetic experiment on methyl (p-acetamidobenzoyl-2, 3, 4-tri-O-acetyl-β-D-glucopyranosid) uronate. It was concluded that p-aminobenzoyl glucuronidehas a pyranose configuration.
2. p-Aminobenzoyl glucuronide isolated from the dog urine was rapidly hydrolyzed by a rabbit-liver β-glucuronidase preparation.

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Metabolism of Drugs. XXXIV. Studies on the Ring Structure of p-Aminobenzoyl Glucuronide isolated from the Urine of Dog administered with p-Aminobenzoic Acid.(2)

Keitaro Kato, Kazuo Yoshida, Hisao Tsukamoto

1962 Volume 10 Issue 12 Pages 1242-1249
Published: December 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1242

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PABA-GA was oxidized with periodate toidentify the ring structure of this compound. The dialdehyde from PABA-GA was examined by reducting it to the corresponding alcohol. The presence of glycerol instead of glyceric acid in the hydrolyzate of the resulting alcohol was established by paper chromatography and the glycerol was identified as the crystalline tris-p-nitrobenzoate. The presence of glycerol in the hydrolyzate suggested that the dialdehyde from PABA-GA exists in the cyclic form.
Periodate oxidation of synthetic 2-naphthyl-β-D-glucopyranosiduronamide and 2-naphthyl-β-D-glucofuranosiduronamide was conducted to compare the two compounds in the rate of periodate consumptioll and the production of acid. There is a good agreement between PABA-GA and 2-naphthyl-β-D-glucopyranosiduronamide with respect to the type of periodate oxidation. In view of above findings it was surmised that PABA-GA has a pyranose configuration.

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Synthesis of Quinolizine Derivatives. XIII. On the Relationship between Chemical Structure and Uterus Contracting Action of Quinolizidine Derivatives, and Synthesis of Some of these Derivatives

Sadao Ohki, Yoshiya Noike, Ichiro Matsuo, Fumiko Hamaguchi, Tokuko Yan ...

1962 Volume 10 Issue 12 Pages 1250-1254
Published: December 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1250

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3-Butyl-, 3-pentyl-, 3-isopentyl-, and 3-phenethylquinolizidines were found to have a comparatively strong uterus-contracting action like that of sparteine.

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Antiviral Effect of Zinc Complexes on Japanese B Encephalitis Virus

Sumiyuki Akihama, Shigeshi Toyoshima

1962 Volume 10 Issue 12 Pages 1254-1257
Published: December 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1254

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Zinc complexes of glycine, DL-alanine, L-cysteine, DL-phenylalanine, L-leucine, DL-lysine, L-tyrosine, DL-methionine, DL-asparagine, DL-aspartic acid, 2-picolinic acid, 8-hydroxyquinoline, guanidine, diethyldithiocarbamic acid, diphenylthiocarbazone, 3, 4-dimercaptotoluene, 1, 10-phenanthroline, 1, 10-phenananthroline-3, 4-dimercaptotoluene and corticotropin, and protamine zinc insulin were prepared and their antiviral activites were examined.
Among these, the zinc complexes of both asparagine and 1, 10-phenanthroline-3, 4-dimercaptotoluene were found to be fairly effective on the Nakayama strain of Japanese B encephalitis virus in vivo.

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Synthesis of Methyl 1, 2-O-Isopropylidene-3-oxo-5-O-acetyl-D-glucofuranuronate

Morizo Ishidate, Zenzo Tamura, Toshio Kinoshita

1962 Volume 10 Issue 12 Pages 1258-1259
Published: December 25, 1962
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.10.1258

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Über eine Reaktion der N-Oxyde der Chinolin-Reihe mit Bleitetraacetat

Akihiro Ohta, Eiji Ochiai

1962 Volume 10 Issue 12 Pages 1260-1261
Published: December 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1260

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Corrigenda for Chemical & Pharmaceutical Bulletin

1962 Volume 10 Issue 12 Pages e1a
Published: 1962
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.10.12_e1a

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Corrigenda for Chemical & Pharmaceutical Bulletin

1962 Volume 10 Issue 12 Pages e1b
Published: 1962
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.10.12_e1b

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Corrigenda for Chemical & Pharmaceutical Bulletin

1962 Volume 10 Issue 12 Pages e1c
Published: 1962
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.10.12_e1c

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Corrigenda for Chemical & Pharmaceutical Bulletin

1962 Volume 10 Issue 12 Pages e1d
Published: 1962
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.10.12_e1d

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Corrigenda for Chemical & Pharmaceutical Bulletin

1962 Volume 10 Issue 12 Pages e1e
Published: 1962
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.10.12_e1e

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Corrigenda for Chemical & Pharmaceutical Bulletin

1962 Volume 10 Issue 12 Pages e1f
Published: 1962
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.10.12_e1f

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Corrigenda for Chemical & Pharmaceutical Bulletin

1962 Volume 10 Issue 12 Pages e1g
Published: 1962
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.10.12_e1g

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Corrigenda for Chemical & Pharmaceutical Bulletin

1962 Volume 10 Issue 12 Pages e2a
Published: 1962
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.10.12_e2a

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Corrigenda for Chemical & Pharmaceutical Bulletin

1962 Volume 10 Issue 12 Pages e2b
Published: 1962
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.10.12_e2b

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Corrigenda for Chemical & Pharmaceutical Bulletin

1962 Volume 10 Issue 12 Pages e2c
Published: 1962
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.10.12_e2c

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Corrigenda for Chemical & Pharmaceutical Bulletin

1962 Volume 10 Issue 12 Pages e2d
Published: 1962
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.10.e2d

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Corrigenda for Chemical & Pharmaceutical Bulletin

1962 Volume 10 Issue 12 Pages e2e
Published: 1962
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.10.e2e

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Corrigenda for Chemical & Pharmaceutical Bulletin

1962 Volume 10 Issue 12 Pages e2f
Published: 1962
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.10.e2f

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Corrigenda for Chemical & Pharmaceutical Bulletin

1962 Volume 10 Issue 12 Pages e2g
Published: 1962
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.10.e2g

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Corrigenda for Chemical & Pharmaceutical Bulletin

1962 Volume 10 Issue 12 Pages e3a
Published: 1962
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.10.12_e3a

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Corrigenda for Chemical & Pharmaceutical Bulletin

1962 Volume 10 Issue 12 Pages e3b
Published: 1962
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.10.12_e3b

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Corrigenda for Chemical & Pharmaceutical Bulletin

1962 Volume 10 Issue 12 Pages e3c
Published: 1962
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.10.12_e3c

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Corrigenda for Chemical & Pharmaceutical Bulletin

1962 Volume 10 Issue 12 Pages e3d
Published: 1962
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.10.12_e3d

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Corrigenda for Chemical & Pharmaceutical Bulletin

1962 Volume 10 Issue 12 Pages e4a
Published: 1962
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.10.12_e4a

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Corrigenda for Chemical & Pharmaceutical Bulletin

1962 Volume 10 Issue 12 Pages e4b
Published: 1962
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.10.12_e4b

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Corrigenda for Chemical & Pharmaceutical Bulletin

1962 Volume 10 Issue 12 Pages e4c
Published: 1962
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.10.12_e4c

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Corrigenda for Chemical & Pharmaceutical Bulletin

1962 Volume 10 Issue 12 Pages e4d
Published: 1962
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.10.12_e4d

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