Chemical and Pharmaceutical Bulletin

Researches on Chemotherapeutic Drugs against Viruses. XXXIV. Syntheses and Antiviral Activity of 10-(ω-Dialkylaminoalkyl)-alkylphenothiazine and N-Substituted 10-Glycyl-alkylphenothiazine.

Atsushi Takada, Hiroko Nishimura

1962 Volume 10 Issue 1 Pages 1-8
Published: January 25, 1962
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.10.1

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Fifteen compounds of 10-(ω-dialkylaminoalkyl)-alkylphenothiazine series, nine compounds of 10-(2-pyridiniumacetyl)-alkylphenothiazine series, three compounds of 10-[2-(1-piperidyl)-acetyl]-alkylphenothiazine series, and three compounds of 10-(2-trimethyl-ammoniumacetyl) alkylphenothiazine iodide series, which were substituted with alkyl group in 1-, 2-, or 3-position of the phenothiazine ring, were synthesized and their antiviral activity on adenovirus was tested by the tissue culture method. Among these compounds, 10-(3-diethylaminopropyl)-3-methyl-and 10-(3-diethylaminopropyl)-3-ethylphenothiazine, and all compounds of 10-(2-pyridiniumacetyl)-alkylphenothiazine chloride series were found to possess direct inactivating effect on the adenovirus. On cytopathogenic effect induced by adenovirus, 10-(3-diethylaminopropyl)-3-methyl and 10-(3-diethylaminopropyl)-3-ethyl derivatives also inhibited in 5×TCD₅₀ of virus.

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Synthesis and Antimicrobial Activity of N¹-(2-Alkylthio-6-alkoxy-4-pyrimidinyl) sulfanilamide.

Tadakazu Tsuji, Sumiko Watanabe, Yasuko Nakadai, Shigeshi Toyoshima

1962 Volume 10 Issue 1 Pages 9-13
Published: January 25, 1962
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.10.9

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N¹-(2-Alkylthio-6-alkoxy-4-pyrimidinyl) sulfanilamide and N¹-[2, 6-bis (alkylthio)-4-pyrimidinyl] sulfanilamide were synthesized and were screened for their antibacterial activity using Escherichia coli C₁₄ and K₁₂, Aerobactor aerogenes 1033, Salmonella enteritidis No. 11, Staphylococcus aureus Terashima. N¹-(2-Methylthio-6-methoxy (and ethoxy)-4-pyrimidinyl) sulfanilamides were effective on some of these bacteria. The latter compound had an effect comparable to that of sulfadimethoxine.

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Studies on Sulfur-containing Chelating Agents. VII. Syntheses of β-Mercaptothiolic Acid Esters and their Metal Chelates.

Hisashi Tanaka, Akira Yokoyama

1962 Volume 10 Issue 1 Pages 13-18
Published: January 25, 1962
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.10.13

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S-Esters of β-mercaptothiohydrocinnamic acid were prepared by the addition of hydrogen sulfide to the S-esters of thiocinnamic acid. S-Methyl, -ethyl, -isopropyl, -butyl, -isopentyl, -dodecyl, -phenyl, and-benzyl esters were prepared and their chelating ability with metals was tested. They formed stable chelates with copper and nickel, and the ratio of ligand to the metal was 1 : 1 in copper chelate and 2 : 1 in nickel, chelate. Cobalt chelate was stable only in the organic solvent, with the ratio of 3 : 1. S-Isopentyl β-mercaptothiohydrocinnamate was very sensitive with nickel and recognizable limit of nickel by this compound was 0.05γ/0.05 cc.

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Studies on Sulfur-containing Chelating Agents. VIII. Syntheses of α, β-Unsaturated β-Mercapto-acid Esters and their Metal Chelates.

Hisashi Tanaka, Akira Yokoyama

1962 Volume 10 Issue 1 Pages 19-24
Published: January 25, 1962
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.10.19

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α, β-Unsaturated β-mercapto-acid esters were prepared and their chelating ability with metals was investigated. α, β-Unsaturated β-mercapto-acid esters formed stable chelates with copper, nickel, cobalt, and iron. These chelates involve conjugated double bond in the chelate ring, so that they were more stable than the chelates without a conjugated double bond. The ratio of the ligand to the metal was found to be 1 : 1 or 2 : 1 in copper chelates, 2 : 1 in nickel chelates, 3 : 1 in cobalt chelates, and 3 : 1 in iron chelates. The preparation of α, β-unsaturated β-mercaptoketones was planned but the substance obtained was present in a thioxo form and did not have a chelating ability.

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Studies on Sulfur-containing Chelating Agents. IX. Syntheses of Alkyl or Aryl o-Mercaptophenyl Ketones, Esters of o-Mercaptobenzoic Acid, S-Esters of o-Mercaptothiobenzoic Acid, and their Metal Chelates.

Hisashi Tanaka, Akira Yokoyama

1962 Volume 10 Issue 1 Pages 25-31
Published: January 25, 1962
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.10.25

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Alkyl or aryl o-mercaptophenyl ketones, esters of o-mercaptobenzoic acid and S-esters of o-mercaptothiobenzoic acid were synthesized, expecting their strong chelating ability due to the presence of aromatic mercapto group and double bond of benzene ring. Alkyl or aryl o-mercaptophenyl ketones were unstable and could not be investigated in detail. Esters of o-mercaptobenzoic acid and S-esters of o-mercaptothiobenzoic acid formed a chelate with cobalt, nickel, and copper in a ratio of 3 : 1, 2 : 1, and 1 : 1, respectively. These ligands were sensitive to nickel and palladium.

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Studies on Phenanthrene Derivatives. IV. Syntheses of 2, 3 : 5, 6-Bismethylenedioxy and 2, 3 : 6, 7-Bismethylenedioxyphenanthrene and Ultraviolet Absorption Spectra of Certain Methylenedioxyphenanthrenes.

Hideaki Shirai, Noriichi Oda

1962 Volume 10 Issue 1 Pages 31-37
Published: January 25, 1962
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.10.31

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2, 3 : 5, 6-Bismethylenedioxyphenanthrene (X) and 2, 3 : 6, 7-bismethylenedioxyphenanthrene (XI) were synthesized from 6-nitropiperonal (I) and homopiperonylic acid (II) by the Pschorr reaction. The structure of the compounds was determined by an unequivocal synthesis using 6-bromopiperonylic acid. The ultraviolet absorption spectra of several kinds of phenanthrenes possessing methylenedioxy group at 2, 3-or 3, 4-position were determined in ethanolic solution.

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Studies on Digitalis Glycosides. XI. Isolation of Digipronin, Purpnin, and Purpronin.

Daisuke Satoh, Hiroshi Ishii, Yohko Oyama, Tamotsu Okumura

1962 Volume 10 Issue 1 Pages 37-42
Published: January 25, 1962
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.10.37

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Three new digitanol glycosides (digipronin, purpnin, and purpronin) were isolated from the water-soluble fraction of the leaves of Digitalis purpurea L. On hydrolysis, digipronin gave three aglycones (α-, β- and γ-digiprogenin) and one molecule of d-digitalose, and purpnin and purpronin gave purpnigenin and purprogenin respectively together with three molecules of d-digitoxose. It is likely that these aglycones belong to a C₂₁-steroid of pregnenolone type. A method for distinguishing the diginigenin type and the pregnenolone type of digitanol glycosides was also described.

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Studies on Digitalis Glycosides. XII. Structures of Digipronin and Digiprogenin.

Daisuke Satoh

1962 Volume 10 Issue 1 Pages 43-51
Published: January 25, 1962
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.10.43

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Digipronin, a digitanol glycoside, and its aglycone, γ-digiprogenin, were respectively converted to isodigipronin and its aglycone, α-digiprogenin, by treatment with dilute alkali or acid. On refluxing with acid, α-digiprogenin lost an element of water and formed β-digiprogenin. The structure of the &lrtri;⁴-3-oxo compound, obtained from β-digiprogenin by reduction with acetic acid and zinc dust followed by Oppenauer oxidation, was established as 14β, 17α-pregn-4-ene-3, 11, 15, 20-tetrone by comparison with the product of isomerization of pregn-4-ene-3, 11, 15, 20-tetrone with alkali or acid. Consequently, the structure of β-digiprogenin was presumed as 3β-hydroxy-14β-pregna-5, 16-diene-11, 15, 20-trione and the tertiary hydroxyl group in α-and γ-digiprogenin would be located at 17-position. In view of the stability of α-digiprogenin to dilute alkali or acid and its negative contribution to optical rotation compared to γ-digiprogenin, it would be appropriate to give the structure of 3β, 17α-dihydroxy-14β-pregn-5-ene-11, 15, 20-trione and 3β, 17α-dihydroxypregn-5-ene-11, 15, 20-trione to α-and γ-digiprogenin, respectively. Digipronin is a monodigitaloside of γ-digiprogenin.

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Studies on Tertiary Amine Oxides. X. Alkaline Ferricyanide Oxidation of Some Aromatic N-Oxides.

Masatomo Hamana, Motoyoshi Yamazaki

1962 Volume 10 Issue 1 Pages 51-54
Published: January 25, 1962
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.10.51

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Alkaline ferricyanide oxidation of some aromatic N-oxides was examined. Quinoline 1-oxide, lepidine 1-oxide, and isoquinoline 2-oxide were smoothly oxidized to the corresponding N-hydroxy-carbostyrils or-isocarbostyrils. From quinaldine 1-oxide, only a small amount of quinaldinic acid 1-oxide was obtained. In contrast, pyridine and nicotinic acid 1-oxide were not affected by this oxidation procedure.

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Synthesis of 1-Substituted 4-Phenyl-4-piperidinol Derivatives as Possible Analgesic.

Nobuo Itoh

1962 Volume 10 Issue 1 Pages 55-60
Published: January 25, 1962
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.10.55

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1-Phenethyl-and 1-[2-(N-alkylanilino)ethyl]-3-alkyl-4-piperidinepropionates were synthesized for physiological evaluation as analgesics. Phenethylamine was condensed with formaldehyde and various alkylmalonic acids, followed by decarboxylation and esterification, to furnish the corresponding 2-alkyl-3-phenethylaminopropionates, which were also prepared from the same amine and 2-alkylacrylates. These were then converted to 3, 3'-(phenethylimino) dipropionic ester derivatives, which were condensed by the Dieckmann method and the crude keto esters were directly submitted to ketonic fission. 1-Phenethyl-3-alkyl-4-piperidinones thus obtained formed a viscous oil, which was allowed to react with phenyllithium and the products were treated with propionic anhydride, to give the ultimate compounds. From N-alkyl-N-Phenylethylenediamine in place of phenethylamine the corresponding piperidinol propionates were similarly prepared. The results of the pharmacological examination of these compounds were described briefly.

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Qualitative and Quantitative Studies on the Cell Wall Carbohydrate in the Yeast, Schizosaccharomyces pombe.

Fusae Kogane, Tomomichi Yanagita

1962 Volume 10 Issue 1 Pages 61-66
Published: January 25, 1962
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.10.61

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The cell wall sample isolated from the mechanically disintegrated cells of the fission yeast, Schizosaccharomyces pombe, was found to be composed of glucan as a major component accompanied with a small amount of peptides. For the quantitative estimation of the wall carbohydrate, the chemical extraction method of Bell and Northcote was employed with slight modifications. The wall carbohydrate content in cells of different ages and in those grown under the influence of anti-yeast antibiotics was estimated.

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Untersuchungen auf dem Gebiet der mikrobiologischen Umsetzung. XVI. Umwandlung von Alkaloiden in der Morphin-Reihe durch Trametes sanguinea. (1).

Kazuaki Iizuka, Michihiro Yamada, Junnosuke Suzuki, Isawo Seki, Ko Aid ...

1962 Volume 10 Issue 1 Pages 67-70
Published: January 25, 1962
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.10.67

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Trametes sanguinea (Basidiomycetes) vermochte Thebain (I) uber 14β-Hydroxycodeinon (II) in 14β-Hydroxycodein (III) umzuwandeln.

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Synthesis of Diphosphopyridine Nucleotide Analogs and their Reaction with Dehydrogenases

Mikio Honjo, Yoshiyasu Furukawa, Hiroki Moriyama, Kuniyoshi Tanaka

1962 Volume 10 Issue 1 Pages 73-75
Published: January 25, 1962
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.10.73

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Metabolites of p-Dimethylaminoazobenzene in Rat Bile

Morizo Ishidate, Zenzo Tamura, Terumi Nakajima, Keijiro Samejima

1962 Volume 10 Issue 1 Pages 75-76
Published: January 25, 1962
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.10.75

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Eine verbesserte Uberfuhrung der Cinchona-Alkaloide der Chinolin-Reihe in diejenigen der Indol-Reihe

Eiji Ochiai, Hideyo Kataoka, Toshiyuki Dodo, Makoto Takahashi

1962 Volume 10 Issue 1 Pages 76-79
Published: January 25, 1962
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.10.76

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