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Shigeshi Toyoshima, Takeo Ueda, Yoshiko Seto
1963 Volume 11 Issue 1 Pages
1-5
Published: January 25, 1963
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The accelerating effect of arginine on cytophatic effect of adeno virus was investigated by using such cell lines as HeLa wild type, HeLa S
8 strain, FL and Hep. No.2 cells. The effect of arginine in promoting a cytophatic effect was demonstrated in the Hep. No.2 cells-arginine-rich maintenance medium system. In the investigation on the effect of 3-(alkoxyphenoxy)-1, 2-propandiols on adeno virus, the use of the Hep. No.2 cells-arginine-rich maintenance medium system was found to be most promising for the screening test of anti-adeno compounds.
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Shigeshi Toyoshima, Takeo Ueda, Tadakazu Tsuji, Yoshiko Seto, Junko No ...
1963 Volume 11 Issue 1 Pages
5-9
Published: January 25, 1963
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The inhibitory effect of guanidine nitrate on the growth of several small animal viruses was investigated. It was found that guanidine inhibited the growth of both poliomyelitis and measles viruses. The findings presented in this report suggest that guanidine inhibits the intracellular multiplication of these viruses and block the replication mechanism of the viruses.
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Hisao Tsukamoto, Hidetoshi Yoshimura, Hiroyuki Ide
1963 Volume 11 Issue 1 Pages
9-13
Published: January 25, 1963
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The metabolic fate of secobarbital [5-allyl-5-(1-methylbutyl) barbituric acid] in rabbits were studied and two main metabolites were isolated in addition to the unchanged secobarbital. The structure of the metabolites were established as 5-allyl-5-(1-methyl-3-carboxypropyl)-and 5-allyl-5-(1-methyl-3-hydroxybutyl) barbituric acid.
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Hisashi Nogami, Shoji Awazu, Yoshio Kanakubo
1963 Volume 11 Issue 1 Pages
13-18
Published: January 25, 1963
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1) Sodium lauryl sulfate (SLS) was hydrolysed in acidic solution at a high temperature, and the rate of hydrolysis was dependent on not only H
+ concentration but also SLS. concentration. It was recognized that the rate of reaction was increased strikingly in the region of a certain concentration of SLS. 2) When the Critical micelle concentration (CMC) of SLS was determined by solubilization method with dye (Sudan III), it was approximately coincident with region of a certain concentration where the rate of reaction increased strikingly. 3) On the contrary to acidic solution, in alkaline solution, SLS above the CMC was a little more stable than that of below.
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Mitsuko Asai, Satoru Kuwada
1963 Volume 11 Issue 1 Pages
18-22
Published: January 25, 1963
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6-Methyl-7-(2-hydroxy-2-methyl-3-oxobutyl) ribolumazine (III) was synthesized by the method of Cresswell and Wood, and the product was found to be converted to riboflavin at pH 1.0, but action of the enzyme of Eremothecium ashbyii on III in vitro produced neigher riboflavin nor 6-methyl-7-hydroxyribolumazine.
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Mitsuko Asai, Komei Mizuno, Satoru Kuwada
1963 Volume 11 Issue 1 Pages
23-28
Published: January 25, 1963
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It was evidenced that action of the enzyme of Eremothecium ashbyii on 6, 7-dimethylribolumazine produced formaldehyde and formic acid, besides riboflavin, and 6-methyl-7-hydroxyriboumazine. The experimental data obtained support the mechanism suggested by Plaut for the formation of riboflavin. As for the formation of 6-methyl-7-hydroxyribolumazine, however, it has been proved that the compound was produced by oxidative rupture of the 7-methyl group of 6, 7-dimethylribolumazine, and this result gave an experimental ground to the assumption of Korte, et al.
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Masaru Ogata, Hideo Kano
1963 Volume 11 Issue 1 Pages
29-35
Published: January 25, 1963
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3-Methylpyridazine 1-oxide (II) and 2-oxide (III) were separated from the N-oxidation products of 3-methylpyridazine (I). Nitration of II could not be accomplished, but III gave 3-methyl-mononitropyridazine 2-oxide (VI) in good yield. The nitro group of VI was proved to be in 5-position. Reaction of 3-methyl-6-methoxypyridazine 2-oxide (IX) with phosphoryl chloride gave 3-methyl-5-chloro-6-methoxypyridazine (XIX) and with acetic anhydride gave 6-methoxy-3-pyridazinemethanol acetate (XXI).
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Masaru Ogata, Hideo Kano
1963 Volume 11 Issue 1 Pages
35-39
Published: January 25, 1963
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4-Methylpyridazine 1-oxide (IV) and 2-oxide (V) were synthesized from 4-methylpyridazine (III). Nitration of IV could not be accomplished, but V gave 4-methyl-mononitropyridazine 2-oxide (XIV) in low yield. The nitro group of XIV was proved to be in 5-position.
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Haruyuki Watanabe, Masaru Ogata, Hideo Kano
1963 Volume 11 Issue 1 Pages
39-44
Published: January 25, 1963
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Dipole moments of 3- and 4-methylpyridazine N-oxides and their related compounds were measured in order to determine the positions of N→O group in these compounds, and the following conclusions were derived. 1. It was confirmed that IV was 1-oxide and III and V were 2-oxides. 2. In 4-methyl derivatives, VIII and IX are 1-oxides and XI and XII are 2-oxides.
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Masayasu Kimura
1963 Volume 11 Issue 1 Pages
44-50
Published: January 25, 1963
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The inhibitory action of organophosphates against acetylcholine (ACh), and cholinesterase (ChE) in vitro and in vivo has been observed using parathion, methylparathion, DFP, DDVP, dipterex, metasystox and TEPP. These experiments gave the following results : 1) The investigated organophosphates produced more and less a reversible inhibitory effect against ACh upon the isolated intestinal segments of mice. The stronger anti-ChE agent (e.g. DFP, TEPP) produced a terrible rhythmical motility, but was remarkably less effective inhibiting against ACh than parathion which was found as a comparatively strong anti-ACh agent. 2) The after-effect of DFP and parathion was observed in intestinal muscle and its difference produced by having an affinity for such two different points of action as ChE and ACh receptor was discussed. 3) Anti-ACh activity and anti-ChE activity in vitro (by Warburg method) and in vivo (by the fall effect of blood pressure) of the above organophosphates were measured and compared with each other. The more effective anti-ACh activity was, the less effective anti-ChE activity was. 4) The antiacetylcholine action by some of organophosphates were measured using the rectus abdominis of frog treated with neostigmine, and then were compared with anti-ChE effects and lethal doses (LD 50) to suggest the possibility that the organophosphorus poisoniong in mammals is also produced by blocking ACh, besides inhibiting ChE.
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Masayasu Kimura, Toshiji Igarashi, Sadao Iwashita
1963 Volume 11 Issue 1 Pages
51-57
Published: January 25, 1963
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In order to study the mode of action of parathion upon acetylcholine (ACh) receptor, its inhibitory effect against ACh was examined with Magnus method using the isolated intestine of mice. These experiments gave following results : 1) From the result of a shift effect of parathion on the dose response curve of ACh, the mode of action of parathion was shown to be a competitive inhibition against ACh at doses less than 5×10
-6M, but to be a non-competitive inhibition at doses greater than about 10
-5M. 2) In the com petitive inhibitiory effect, the estimation of the reaction order n was not significantly different from a supposed value 1, while the n was estimated as 1.5 in the case of the non-competitive inhibition. From this fact, it was condluded that one parathion molecule antagonises one ACh molecule at ACh receptor. 3) Likewise, the reaction order n of PAM against ACh was examined by Magnus method and ACh against ChE by Warburg method, and both were estimated as 1. 4) Using parathion, PAM and atropine, the interactions between two of them to an ACh receptor were demonstrated, and all of the three pairs were shown to have relationship of additive synergism. Therefore, it was confirmed that the point of action of parathion as well as atropine is the ACh receptor.
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Masuo Akagi, Setsuzo Tejima, Masanobu Haga
1963 Volume 11 Issue 1 Pages
58-61
Published: January 25, 1963
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1, 6-Anhydro-1, 6-sulfide-2, 3, 4-tri-O-acetyl-β-D-glucopyranose was synthesized by alkali-degradation and successive acetylation of 6-O-tosyl-2, 3, 4-tri-O-acetyl-β-D-glucopyranosyl ethylxanthate and 6-O-tosyl-1-deoxy-1-acethylthio-2, 3, 4-tri-O-acetyl-β-D-glucopyranose, which were prepared from 6-O-tosyl-2, 3, 4-tri-O-acetyl-α-D-glucopyranosyl bromide with potassium ethylxanthate and potassium thiolacetate respectively. On desulfurization of 1, 6-anhydro-1, 6-sulfide-2, 3, 4-tri-O-acetyl-β-D-glucopyranose with Raney nickel, 6-deoxy-1, 5-anhydro-D-sorbitol tracetate was obtained. 1, 6-Dideoxy-1, 6-diacetylthio-2, 3, 4-tri-O-acetyl-β-D-glucopyranose was prepared from 6-deoxy-6-acetylthio-2, 3, 4-tri-O-acetyl-α-D-glucopyranosyl bromide, which was synthesized from 6-deoxy-6-acetylthio-1, 2, 3, 4-tetra-O-acetyl-β-D-glucopyranose, and potassium thiolacetate. The structure was also confirmed by desulfurization with Raney nickel according to give 6-deoxy-1, 5-anhydro-D-sorbitol.
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Masuo Akagi, Yoneshiro Oketani, Masahiko Takada
1963 Volume 11 Issue 1 Pages
62-67
Published: January 25, 1963
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Two methods are described for the estimation of 2-methyl-3-o-tolyl-4 (3H)-quinazolinone (MTQ) in biological fluids and tissues. In the first, MTQ is extracted from alkalinized biological material with hexane, the solvent is evaporated, and the residue is dissolved in dilute hydrochloric acid, and measured spectrophotometrically at 234mμ. The second, suitable for tissues, is the method in which normal biological blank becomes negligible by geometrical treatment of its absorbances at three wave lengths. These procedures permit the determination of MTQ in amounts as 1 μg./cc. of final measurement solution. The methods are specific for MTQ in that they do not include any transformation products of the compound.
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Yasuo Makisumi, Hideo Kano
1963 Volume 11 Issue 1 Pages
67-75
Published: January 25, 1963
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5-Methyl-7-methoxy-s-triazolo [1, 5-a] pyrimidine (IVa) was prepared by the reaction of the 7-chloro compound III with sodium methoxide at below room temperature. The property of the 7-alkoxy derivatives (IVa and IVb) was examined and it was discovered that the alkyl group of these derivatives undergoes rearrangement to the ring nitrogen at 3- and 4-positions. In order to determine the structure of the products being obtained by above rearrangement, the reaction of ethyl acetoacetate with 5-alkylaminos-triazoles (XIVa and XIVb) and 4-alkyl-5-aminos-triazoles (XVa and XVb) which were prepared from 1-alkyl-2-aminoguanidinium sulfates (XIIa and XIIb), was investigated.
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Toyozo Uno, Koichiro Miyajima
1963 Volume 11 Issue 1 Pages
75-80
Published: January 25, 1963
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A new volumetric determination of ethylene oxide content in nonionics was established with sodium tetraphenylborate as a titrant using Congo red as an indicator. This method can be applied to nonionics containing more than 10 units of ethylene oxide. A linear relationship between the units of ethylene oxide and the volume of sodium tetraphenylborate was obtained that six units of ethylene oxide combined with one mole of sodium tetraphenylborate. The accuracy of this titration is about ±3%.
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Toyozo Uno, Koichiro Miyajima
1963 Volume 11 Issue 1 Pages
80-82
Published: January 25, 1963
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In the preceding paper, the titrimetry of nonionics was established with both sodium tetraphenylborate and barium chloride. In this work, the composition of the nonionicsbarium-tetraphenylborate complex was studied by Morgan's method, Neu's method, and gravimetry. It was found that 6 moles of ethylene oxide combined with 1 mole of tetraphenylborate and 0.5 mole of barium in the complex in 10∼40 units ethylene oxide condensates and the titrimetry was applicable to the determination of the ethylene oxide content in nonionics.
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Takanobu Itai, Sachiko Natsume
1963 Volume 11 Issue 1 Pages
83-90
Published: January 25, 1963
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Pyridazine 1-oxide (I) was nitrated to 4-nitropyridazine 1-oxide (II) with a mixed acid under a vigorous condition. The structure of II was confirmed as follows. i) Hydrogenation of II itself and methoxypyridazine 1-oxide (VI), derived from II, gave the known 4-aminopyridazine and 4-methoxypyridazine, respectively. ii) Pyridazinol 1-oxide obtained by hydrolysis of VI formed N-methoxypyridazinone with methyl p-toluenesulfonate and sodium methoxide. iii) VI was identical with the compound obtained by hydrogenation of 4-methoxy-3, 6-dicholoropyridazine 1-oxide, whose structure was established by its correlation to the known 3, 4, 6-trimethoxypyridazine 1-oxide. In addition, some reactions related to II were described.
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Katsura Morita, Shunsaku Noguchi, Hiroshi Kono, Takuichi Miki
1963 Volume 11 Issue 1 Pages
90-94
Published: January 25, 1963
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Chlorination of diosgenin acetate followed by treatment with performic acid, dechlorination, and hydrolysis has given pregn-5-ene-3β, 16β, 20α-triol in 60∼70% overall yield. When the chlorination was conducted in a dimethylformamide solution, the main product was 3β-acetoxy-5-chloro-6β-formyloxy-5α, 25D-spirostan. Validity of this novel reaction was confirmed by expriments in the cholesterol series. Synthesis of 9α-chloro-11β-formyloxysteroids from ⊿
9(11)-steroids has also been facilitated.
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Takuichi Miki, Katsura Morita, Shunsaku Noguchi, Toyokazu Kishi, Kenta ...
1963 Volume 11 Issue 1 Pages
95-103
Published: January 25, 1963
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In view of the finding that 5α-pregnane-3β, 5, 6β, 16β, 20α-pentol (POL) shows an interesting sodium excreting activity similar to that of SEF in the animal test, a number of polyoxygenated pregnanes possessing the hydroxyl or the carbonyl groups at the positions of C-3, C-5, C-6, C-16, and C-20 were synthesized. Syntheses of 3β, 5, 6β, 16α-tetrahydroxy-5α-pregnan-20-one-a hybrid compound of POL and SEF-was also described.
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Hayao Nawa, Masao Uchibayashi, Akira Okabori, Katsura Morita, Takuichi ...
1963 Volume 11 Issue 1 Pages
103-108
Published: January 25, 1963
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5α-Pregnane-3β, 5, 6β, 20α-tetrol (IIIa), 5α-pregnane-3β, 5, 6β, 20β-tetrol (IV), 5α-pregnane-3β, 6β, 16β, 20α-tetrol (VIIIa), 5α-pregnane-3β, 6α, 16β, 20α-tetrol (XIa), and 5α-pregnane-3β, 6α, 16β, 20β-tetrol (XIII) were synthesized according to the schemes shown in Chart 1 and Chart 2.
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Masanobu Terasaka, Kazuko Yamamoto, Yutaka Kawazoe
1963 Volume 11 Issue 1 Pages
108-114
Published: January 25, 1963
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The structures of N-methylorixidinine, N-methylisoorixidinine and N-methylorixidine have been verified by NMR analysis. In addition, the conformation of the substituents on dihydrofuran ring was discussed, based on the relationship between the dihedral angle and the spin coupling constant.
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Tatsuya Horie, Takeo Ueda
1963 Volume 11 Issue 1 Pages
114-122
Published: January 25, 1963
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It was found that N-oxidation of 3-acetamidopyridazine gave a mixture of 1-oxide and 2-oxide and the 2-oxide had a tautomeric N-acetoxy from, while N-oxidation of 3-acetamido-6-methoxypyridazine, 3-amino-6-methoxypyridazine and 3-amino-6-chloropyridazine afforded exclusively 2-oxide.
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Shigeru Kobayashi, Sumiko Tagawa, Shigeko Nakajima
1963 Volume 11 Issue 1 Pages
123-126
Published: January 25, 1963
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The Reimer-Tiemann reaction of m-iodophenol yielded three products in contrast with literature reported by Hodgson and Jenkinson and the products were confirmed unambiguously to be 2-iodo-4-hydroxy-, 2-hydroxy-6-iodo-, and 2-hydroxy-4-iodo-benzaldehydes, respectively.
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Shingo Matsumura, Shuichi Seto
1963 Volume 11 Issue 1 Pages
126-128
Published: January 25, 1963
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The reaction of 1 : 3 mole ratio of 6-dimethylamino-3, 4-fulvene dicarboxaldehyde or 6-hydroxy-3, 4-fulvenedicarboxaldehyde and malononitrile, in the presence of base, easily formed stable cyclopentadienyl salt derivatives.
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Yasuo Makisumi
1963 Volume 11 Issue 1 Pages
129-131
Published: January 25, 1963
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The alkylation of 5-methyl-s-triazolo [1, 5-a] pyrimidin-7-ol (I) with alkyl iodide and dialkyl sulfate always afforded the two N-alkylated products (IIa-b and IIIa-b). The structure of these products was established to be 4-alkayl-5-methyl-s-triazolo [1, 5-a]-pyrimidin-7 (4H)-ones and 3-alkyl-5-methyl-s-triazolo [1, 5-a] pyrimidin-7 (3H)-ones respectively.
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Michiyasu Sugii, Shigeharu Nagasawa, Tomoji Suzuki
1963 Volume 11 Issue 1 Pages
135-136
Published: January 25, 1963
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Eiji Ochiai, Makoto Takahashi, Yoshikazu Tamai, Hideyo Kataoka
1963 Volume 11 Issue 1 Pages
137-138
Published: January 25, 1963
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