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Michiko Kagawa
1959 Volume 7 Issue 7 Pages
751-756
Published: October 20, 1959
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1) The epimers of 2-ethynylborneol were resolved by means of alumina adsorption. They behaved similarly to an anionotropic rearrangement, forming the same product. 2) 2-Ethylborneol was dehydrated in exocyclic way with hydrochloric acid or formic acid to form 2-ethylidenecamphane. 2-Ethylcamphene, which is presumably formed by endocyclic dehydration, was not found. 3) 2-Ethynylborneol yielded aldehyde or ketone by the action of hydrochloric acid or formic acid, respectively. These reactions were studied under varying conditions in order to determine the mechanisms of the rearrangement.
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Kyoji Hayano, Sataro Imado
1959 Volume 7 Issue 7 Pages
756-760
Published: October 20, 1959
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In order to improve some of the defects of PAS preparations now being used, such as the bad taste, inconvenience of administration, and occurrence of side effects, a new complex compound of PAS and aluminum, H
2[(C
7H
5O
3N)
2Al(OH)(H
2O)] was synthesized by the application of 1 mole of aluminum chloride to 2 moles of PAS-sodium in aqueous solution, in the presence of 1 mole of sodium hydrogen carbonate. This substance was found to be a trihydrate or hexahydrate at room temperature. This new complex, Al-PAS, is a dibasic acid and occurs as colorless, fine crystalline powder, without odor and slightly sweet to the taste, becoming astringent later, and dissolves in 2 moles of sodium hydroxide or ammonia water. This alumino-p-aminosalicylic acid was dissolved in 2 moles of ammonia water and 1 mole of calcium chloride was added, from which colorless and tasteless crystals were obtained. Its analytical values agreed with the formula of Ca[(C
7H
5O
3N)
2Al(OH)(H
2O)]·7H
2O.
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Kyoji Hayano, Sataro Imado
1959 Volume 7 Issue 7 Pages
761-766
Published: October 20, 1959
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Crystal water and dissociation vapor pressure of the hydrates of alumino-p-aminosalicylic acid and calcium alumino-p-aminosalicylate were measured. Measurement of loss in weight showed that there are three moles of crystal water in Al-PAS and seven moles in Al-PAS-Ca. Thermobalance method showed that a pentahydrate of Al-PAS-Ca would be present besides the heptahydrate. Al-PAS is labile above 140°and undergoes decomposition but Al-PAS-Ca was found to be comparatively stable even at 180°. Dissociation vapor pressure of the heptahydrate of Al-PAS-Ca was measured and heat of dissociation at around room temperature was calculated. Stability of these complex compounds in the air was also examined.
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Kyoji Hayano, Sataro Imado
1959 Volume 7 Issue 7 Pages
766-771
Published: October 20, 1959
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In order to elucidate chemical structure of alumino-p-aminosalicylic acid, single crystal of calcium alumino-p-aminosalicylate was prepared and its crystallomorphological and optical characteristics were examined. Examination of the presence or absence of the center of symmetry in this salt molecule was made through infrared absorption spectrum and Raman effect. Presence of the spectra with the same frequency in the Raman and infrared spectral measurements indicated the absence of a center of symmetry in the molecule of alumino-p-aminosalicylic acid.
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Kyoji Hayano, Sataro Imado
1959 Volume 7 Issue 7 Pages
772-776
Published: October 20, 1959
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Structural determination of the newly synthesized calcium alumino-p-aminosalicylate was not sufficiently made through chemical means and X-ray crystallographic studies were carried out. By taking oscillation and Weissenberg photographs, size of unit cells and space groups were determined. X-Ray method of calculating the molecular weight from unit cells gave values agreeing with a heptahydrate. Space group was C
1i-P
-1, which indicated the presence of a center of symmetry in the crystal but complete analysis of crystal structure was extremely difficult and therefore, in order to obtain some information of atomic arrangement in the crystal, projection of Patterson function towards the c axis (the shortest period) was made. Closer examination of the Patterson map, combined with packing considerations, revealed that a planar complex ion is possibly arranged parallel in the direction diagonal to the projected unit cell and inclined approximately 82∼83°from the plane of projection.
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Kyoji Hayano, Sataro Imado
1959 Volume 7 Issue 7 Pages
777-779
Published: October 20, 1959
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X-Ray diffraction of calcium alumino-p-aminosalicylate was taken by powder photography, and the angle of diffraction and lattice spacings were calculated from the position of its diffraction patterns, together with relative intensity of diffraction lines. The sample of calcium alumino-p-aminosalicylate heated to 200°in thermal balance was found to contain m-aminophenol. Diffraction was also recorded by the Norelco Diffractometer, and the angle of diffraction and relative intensity obtained from it were compared with those found by the powder method.
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Tatsuo Nakasato, Shozo Nomura
1959 Volume 7 Issue 7 Pages
780-784
Published: October 20, 1959
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The structure of laurolitsine, a new phenolic base of Neolitsea sericea (BLUME) KOIDZ., was established as represented by formula (X).
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Etsuko Toyoura
1959 Volume 7 Issue 7 Pages
785-786
Published: October 20, 1959
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The metabolic activities of 4 strains (KT-230, KT-231, KT-232, and KT-233) of soil bacteria were tested on glutamic and aspartic acids and their benzoyl derivatives, and it was found that benzoyl-DL-glutamic and benzoyl-DL-aspartic acids are resolved by the metabolism of KT-230 and KT-231, but not by KT-232 and KT-233. It was also demonstrated that KT-231 metabolized benzoyl-DL-glutamic and benzoyl-DL-aspartic acids to yield L-amino acids and the corresponding benzoyl-D-amino acids.
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Etsuko Toyoura
1959 Volume 7 Issue 7 Pages
787-788
Published: October 20, 1959
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The metabolic activities of KT-231 and KT-230 were tested on p-methoxyphenylalanine and 3, 4-methylenedioxyphenylalanine and their benzoyl derivatives (Table I). It was demonstrated that one strain (KT-231) of soil bacteria metabolized benzoyl derivatives of p-methoxy-DL-phenylalanine and 3, 4-methylenedioxy-DL-phenylalanine to produce L-amino acids and the corresponding benzoyl-D-amino acids.
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Etsuko Toyoura
1959 Volume 7 Issue 7 Pages
789-790
Published: October 20, 1959
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A certain strain (KT-311) isolated from soil had the metabolic activity shown in Table I and could metabolize α-N-phenylacetyl-ε-N-benzoyl-DL-lysine to produce ε-N-benzoyl-L-lysine and α-N-phenylacetyl-ε-N-benzoyl-D-lysine in good yield. KT-311 could hydrolyse phenylacetyl derivative but not benzoyl derivative of ε-N-benzoyl-L-lysine. KT-311 seemingly belongs to the Pseudomonas group.
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Hideyo Shindo
1959 Volume 7 Issue 7 Pages
791-800
Published: October 20, 1959
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Infrared investigations were made on the hydrogen-bond effect of pyridine 1-oxide and its derivatives with some proton donors. The assignment for N-O stretching frequency (strong absorption in the region of 1190 and 1320 cm
-1) was further confirmed by observing the spectral change of N-oxide compounds following hydrogen-bond formation with methanol in non-polar solvent. The hydrogen-bonding ability of various derivatives was estimated in terms of the magnitude of shift in bonded OH frequency of methanol and an excellent linear relation was found by plotting these frequencies against the σ-values of the substituents. Anomalous behavior in 2-methyl derivatives was also pointed out and discussed. From a comparison of the frequency shift of the carbonyl stretching absorption in methanol and water, it was found that the electron-releasing ability of the N-oxide function towards 4-position of the ring is largely decreased in polar solvent with active hydrogen.
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Yoshinobu Sato
1959 Volume 7 Issue 7 Pages
801-804
Published: October 20, 1959
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9-Azahexahydrojulolidine (III) was prepared by saponification and decarboxylation of 2-cyanoperhydropyrido [3, 4, 5-i, j] quinolizine (II) with hydrochloric acid, obtained by reaction of 9-methyl-9-azahexahydrojulolidine (I) and cyanogen bromide. Series of these compounds was assumed to have the cis-quinolizidine ring and, in order to ascertain this assumption, (III) was converted to 9-azajulolidine (IV).
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Katsumi Tanabe, Rinji Takasaki, Ryozo Hayashi, Makoto Shirasaka
1959 Volume 7 Issue 7 Pages
804-810
Published: October 20, 1959
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Sclerotinia libertiana was found to hydroxylate 2β-position of some Δ
4-3-oxosteroids. This microorganism was incubated with 17α-hydroxyprogesterone, 17α-hydroxydesoxycorticosterone (Reichstein's Substance S), and progesterone as a substrate, and the corresponding 2β-hydroxylated products were obtained. Some additional hydroxylated steroids were obtained and their structure was determined.
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Katsumi Tanabe, Ryozo Hayashi, Rinji Takasaki, Makoto Shirasaka
1959 Volume 7 Issue 7 Pages
811-816
Published: October 20, 1959
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Microbial oxidation of progesterone with Absidia regnieri was carried out and seven kinds of hydroxylated product were isolated. Five of these products possessed at least one hydroxyl in 14α-position and were found to be 14α-hydroxy-, 9α, 14α-dihydroxy-, 7α, 14α-dihydroxy-, 6β, 14α-dihydroxy-, and 7α, 14α, 15β-trihydroxyprogesterone.
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Itiro Yosioka, Hiroshi Hikino, Yasuko Sasaki
1959 Volume 7 Issue 7 Pages
817-820
Published: October 20, 1959
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Hinesol (I) contains an olefinic linkage since it furnished the saturated dihydrohinesol (II) on catalytic hydrogenation. The oxygen atom is present in a tertiary alcoholic group which was readily dehydrated by various agents to form a double bond which, in the case of (I), could conjugate with the original ethylenic linkage. Catalytic reduction of the anhydro derivatives of (I) and (II) gave the saturated bicyclic hydrocarbons. Dehydrogenation of (I) with selenium afforded vetivazulene.
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Nobusuke Kawano
1959 Volume 7 Issue 7 Pages
821-822
Published: October 20, 1959
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The structure of sciadopitysin, C
33H
24O
10, was deduced to be a new-type bisflavonoid of formula (I) on the basis of the degradation product of its triethyl ether (III).
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Fumio Ueda
1959 Volume 7 Issue 7 Pages
823-828
Published: October 20, 1959
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Under the assumption that compounds with hydrophobic group would have antiviral activity, the compounds of 3-(o-alkylphenoxy)-, 3-(p-alkylphenoxy)-, and 3-(o-alkanoylaminophenoxy)-1, 2-propanediol series were synthesized and examined for antiviral activities. 3-Alkylphenoxy-1, 2-propanediols were prepared from fatty acid phenyl esters by their Fries rearrangement to o- and p-alkanoylphenols, Clemmensen reduction to o- and p-alkylphenols, and condensation with 3-chloro-1, 2-propanediol in the presence of sodium ethoxide in ethanol to 3-(o-alkylphenoxy)-and 3-(p-alkylphenoxy)-1, 2-propanediols having alkyl chains of 6∼14 carbon atoms. 3-(o-Alkanoylaminophenoxy)-1, 2-propanediols having alkanoyl chains of 8∼12 carbon atoms were prepared by the condensation of o-alkanoylaminophenols with 3-chloro-1, 2-propanediol in the presence of sodium ethoxide in ethanol. 3-(o-Decanoylaminophenoxy)-1, 2-propanediol had antiviral activity against the Nakayama strain of Japanese B encephalitis virus in vivo. Several compounds of 3-(p-alkylphenoxy)- and 3-(o-alkylphenoxy)-1, 2-propanediol series had antiviral activity against the Lansing strain of poliomyelits virus in vitro.
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Fumio Ueda, Takeo Ueda, Shigeshi Toyoshima
1959 Volume 7 Issue 7 Pages
829-833
Published: October 20, 1959
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In order to study the antiviral effect of alkanoic acid containing alkylphenoxy group in 2-position, 2-alkylphenoxyacetic, -propionic, -butyric, and -valeric acids were synthesized. By the condensation of alkylphenol with ethyl 2-haloalkanoate, ethyl 2-alkylphenoxy-alkanoate was obtained, which was hydrolysed to 2-alkylphenoxyalkanoic acid. o-Hexylphenoxyacetic acid had antiviral activity against Japanese B encephalitis virus in vivo. Several compounds in this series were found to be effective against the PR-8strain of influenza A virus and the Lansing strain of poliomyelitis virus in vitro.
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Fumio Ueda, Takeo Ueda, Shigeshi Toyoshima
1959 Volume 7 Issue 7 Pages
834-836
Published: October 20, 1959
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2-Dimethylaminoethyl phenyl ether, having alkyl chain of 8∼14 carbon atoms on the benzene ring in ortho- or para-position, were synthesized by condensation of alkylphenol with 2-dimethylaminoethyl chloride. The antiviral effects of these compounds were tested against the Nakayama strain of Japanese B encephalitis virus and the Lansing strain of poliomyelitis virus. 2-Dimethylaminoethyl o-octylphenyl ether and p-octylphenyl ether had antiviral activity against the Nakayama strain in vivo. 2-Dimethylaminoethyl o-octylphenyl ether, o-decylphenyl ether, and p-octylphenyl ether had antiviral activity against the Lansing strain in vitro.
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Masayasu Kimura
1959 Volume 7 Issue 7 Pages
837-840
Published: October 20, 1959
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(1) A modified salt solution, which does not contain sodium hydrogen carbonate, was used in this experiment to study the effect of pH on the small intestines of mice. (2) The dose-contraction curve of N-butyltrimethylammonium bromide obeyed Clark's equation and the slope was 1.2. The curve was inhibited competitively in pH range between 6.0 and 5.5. (3) From the interaction between N-butyltrimethylammonium bromide and H
+, the pKa of the anionic site of ACh-receptor was estimated as 6.15 and as 6.16 in the case of ACh and H
+. These values are very close to pKa 6.2 of the anionic site of ACh-esterase, estimated by Wilson and Bergmann.
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Masayasu Kimura
1959 Volume 7 Issue 7 Pages
841-844
Published: October 20, 1959
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(1) The competitive inhibitory action of atropine to acetylcholine was augmented at a lower pH. The synergistic effect of atropine and hydrogen ion was between addition and potentiation. On the contrary, 1, 1-diphenyl-3-piperidino-1-butanol was proved to have an additive effect to atropine in the range of concentration where it has only atropine-like action. A discussion on the curious behavior of H
+ on ACh receptor is presented. (2) The atropine-like activity of 1, 1-diphenyl-3-piperidino-1-butanol was subjected to the same potentiation with H
+ as atropine and the papaverine-like activity of the same compound was hardly affected by H
+ within the range of pH 5.6∼7.4. It was concluded that a specific receptor for papaverine-like action has a strong acidity or that the presence of the receptor must be denied.
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Shoji Takitani
1959 Volume 7 Issue 7 Pages
845-848
Published: October 20, 1959
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(1) The N-glucuronides of primary aliphatic amines, i.e. benzylamine, phenethylamine, ethylamine, isopropylamine, butylamine, isobutylamine, and cyclohexylamine, were prepared. (2) The degree of dissociation and dissociation constants of sodium aryl- and alkyl-amine N-glucosyluronate were determined by measuring their optical rotation.
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Tsutomu Momose, Shujiro Goya
1959 Volume 7 Issue 7 Pages
849-850
Published: October 20, 1959
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Michiyasu Sugii, Risaburo Nakai, Chiaki Tanaka
1959 Volume 7 Issue 7 Pages
851-852
Published: October 20, 1959
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Decarboxylation reaction of carboxylic-carbonic anhydride was studied by using
14C-carboxyl-labeled benzoic acid and phenylacetic acid. It was found that the carbon dioxide was liberated from the ethoxycarbonyl group of the carboxylic-carbonic anhydride.
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Tsutomu Momose, Yo Ueda, Masaru Nakamura
1959 Volume 7 Issue 7 Pages
853
Published: October 20, 1959
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