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Masayasu Kimura
1965 Volume 13 Issue 1 Pages
1-7
Published: January 25, 1965
Released on J-STAGE: March 31, 2008
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In order to determine whether Acetylcholine (ACh) receptor is identical with Cholinesterase (ChE) or not at the pharmacological or functional level, the mechanism of affinity for the active site on ACh receptor surface is considered with the pharmacological and biochemical method using a usefull tool, organophosphoryl choline. These experiments gave following results : 1) By Magnus method using the rectus abdominis of frog, dose-inhibition curve of amyltrimethylammonium salt (ATMA) and dose-inhibition curve of hydrogen ion against it were observed. From the results, one molecule of ATMA combines with an ACh receptor in the process of the contractile response like the case of ACh, and the site of action of hydrogen ion located on the anionic site of ACh receptor. 2) The apparent pKa value of the anionic site of ACh receptor is about 5.92 and very close to that of ChE.3) The two combination constants of organphosphorylcholine with the esteratic site of ACh receptor and of ChE were about 5.53×10
-4 and 4.63∼8.27×10
-3. Therefore, there is the difference between ACh receptor and ChE regarding the esteratic site. 4) From the correlation between anti-ACh and anti-ChE activity of some organophosphorylcholine derivatives, it was indicated that the former increased in the order of -O-■=O, -O-■=S, and -S-■=S, while the latter was the reverse order of them. 5) From the results above mentioned, it may be concluded that ACh receptor is different from ChE molecule.
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Kin-ichi Imai, Mikio Honjo
1965 Volume 13 Issue 1 Pages
7-16
Published: January 25, 1965
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Uridine-5-carboxaldehyde (I), uridien-5-carboxylic acid (II), and 1-(β-D-ribofuranosyluronic acid) uracil-5-carboxaldehyde (III) were isolated and characterized form the reaction products obtained after catalytic oxidation of uridine-5-methanol (IV). Five aldehyde hydrazone derivatives of I and III were synthesized. Catalytic oxidation of several pyrimidine nucleosides gave the corresponding uronic acid derivatives. The ease of the oxidation of these compounds was found different, depending upon the base moieties.
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Yoshiyasu Furukawa, Yoshiko Mizuno, Yasushi Sanno, Mikio Honjo
1965 Volume 13 Issue 1 Pages
16-21
Published: January 25, 1965
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O-Phosphoryl-L-serine (I) was treated with carbobenzyloxychloride to give O-phosphoryl-N-carbobenzyloxy-L-serine (III). Condensation of III with dicyclohexylguanidinium cytidine 5'-phosphoramidate (II) gave cytidine 5'-diphosphate-N-carbobenzyloxy-L-serine (IV), which was hydrogenated with palladised charcoal to obtain cytidine 5'-diphophate-L-serine. Likewise, deoxycytidine 5'-diphosphate-L-serine was synthesized from III and dicyclohexylguanidinium deoxycytidine 5'-phosphoramidate (V).
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Zen-ichi Horii, Yasuhiko Yamawaki, Miyoji Hanaoka, Yasumitsu Tamura, S ...
1965 Volume 13 Issue 1 Pages
22-26
Published: January 25, 1965
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Cis-and trans-2-Hydroxy-2-(2-pyridyl) cyclohexaneacetic acid, (X) and (VIII), were synthesized and their stereochemistries discussed. The latter (VIII) was converted into racemic lactam-carbinol A (I), which showed the same infrared spectrum in chloroform as that of natural lactam-carbinol A obtained by degradation of securinine. The present work proved unequivocally the stereochemistries in B/C ring junctures of lactamcarbinols A (I) and B (II), and quinolizidines A (IV) and B (V), degradation products of securinine.
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Zen-ichi Horii, Miyoji Hanaoka, Masazumi Ikeda, Yasuhiko Yamawaki, Yas ...
1965 Volume 13 Issue 1 Pages
27-32
Published: January 25, 1965
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The Hofmann degradations of tetrahydrosecurinine (II) and tetrahydrosecurininol (III) resulted in N-C
5a ring opening. The former gave two products, a normal methine base (VII) and an abnormal product (VIII), and the latter gave a normal methine base (XIII) alone. These products, (VII), (VIII), and (XIII), were interrelated as follows. Dehydration of VIII followed by hydrogenation gave an amino-lactone (IX), which was also prepared from VII by hydrogenation. On the other hand, lithium aluminum hydride reduction of VII gave XIII, which was converted to an amino-diol (XIV) by hydrogenation. The syntheses of the racemates of IX and XIV provided the proofs for their structures. The result establishes the configuration at C
3a of II.
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Satoshi Mizukami, Masao Kono
1965 Volume 13 Issue 1 Pages
33-39
Published: January 25, 1965
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2'-Mercaptosulfonanilide derivatives were prepared by the reduction of 2, 2'-dithiobissulfonanilide with sodium sulfide and tested as the analytical reagents. These compounds were found to be useful reagents for the identification of copper (II), cobalt (II), and nickel (II), and the spectrophotometric determination of cobalt (II).
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Masao Tomita, Hiroshi Furukawa, Tsang-Hsiung Yang, Tsung-Jen Lin
1965 Volume 13 Issue 1 Pages
39-43
Published: January 25, 1965
Released on J-STAGE: March 31, 2008
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Isoliensinine, a new phenolic biscoclaurine type alkaloid, was isolated from Formosan "Lien Tze Hsin, " loti embryo (embryo of the seed of Nelumbo nucifera GAERTN., Fam. Nymphaeaceae) and its structure was assigned to the formula II on the basis of the cleavage reaction by sodium in liq. ammonia of its O, O-diethyl ether (IV) and of the synthesis of its O, O-dimethyl ether (III).
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Takayuki Wada
1965 Volume 13 Issue 1 Pages
43-49
Published: January 25, 1965
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Digiprolactone is 2, 4-dihydroxy-2, 6, 6-trimethyl-Δ
1, α-cyclohexaneacetic acid γ-lactone and identical with loliolide. The stereochemistry of this compound was also discussed.
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Tokuo Kubota, Keiji Yoshida, Fumiko Hayashi, Ken'ichi Takeda
1965 Volume 13 Issue 1 Pages
50-57
Published: January 25, 1965
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A number of steroidal Δ
1, 4-3-ones (Va∼g) were hydroxylated with osmium tetroxide affording the 1α, 2α-dihydroxy-Δ
4-3-ones (VIa∼g) and the 4α, 5α-dihydroxy-Δ
1-3-ones (VIIa∼g). The former compounds (VIa∼g) were converted into the A-norsteroids having Δ
3(5)-1, 2-dioxo structure (IIIa∼g) by treatment with manganese dioxide at room temperature.
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Shoichi Nakajima, Koono Kinoshita, Shoji Shibata
1965 Volume 13 Issue 1 Pages
58-64
Published: January 25, 1965
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The ozonolysis of anhydroitaconitin which was prepared from itaconitin by the action of acetic or propionic anhydride followed by hydrolysis, yielded, 2, 4-cresotaldehyde liberating acetaldehyde and carbon dioxide. Treatment of the same substance with nitric acid afforded 2, 4, 6-trinitro-m-cresol. These and other experimental results showed that the anhydroitaconitin was an aromatic compound having a m-cresyl grouping with an adjacent ethylenic linkage. The catalytic hydrogenation of anhydroitaconitin in acetone gave dihydroanhydroitaconitin, whereas in alkali gave a carboxylic acid, C
14H
18O
5.
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Shoichi Nakajima
1965 Volume 13 Issue 1 Pages
64-69
Published: January 25, 1965
Released on J-STAGE: March 31, 2008
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Methylanhydroitaconitin (III) which was prepared from anhydroitaconitin by treatment with the methylating agent followed by hydrolysis gave 2-methoxy-4-methylbenzaldehyde on ozonolysis. While the ozonolysis of the compound, C
14H
18O
5, which was obtained by alkaline hydrogenation of anhydroitaconitin yielded cisoid-dihydrohaematinic acid (XI). From these and other experimental results the structure of the compound, C
14H
18O
5 was established as XII.
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Shoichi Nakajima
1965 Volume 13 Issue 1 Pages
69-73
Published: January 25, 1965
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The structural formula of anhydroitaconitin was established as 2-methyl-3-(trans-2-hydroxy-4-methylstyryl) maleic anhydride. The structures of the reaction products of anhydroitaconitin with diazomethane, ο-phenylenediamine or various ketonic reagents, and acetylanhydroitaconitin, propionylanhydroitaconitin, dihydroanhydroitaconitin, dihydroacetylanhydroitaconitin and all other derivatives hitherto prepared were determined. The ultraviolet, infrared and nuclear magnetic resonance data were provided to support these formulae.
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Shoichi Nakajima
1965 Volume 13 Issue 1 Pages
73-78
Published: January 25, 1965
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It was found that itaconitin, a yellow coloring matter of a mould Aspergillus itaconicus KINOSHITA, possesses a 3, 5-dienoic acid system which is converted into an aromatic ring by the action of acetic anhydride to give acetylanhydroitaconitin. Oxidation of hexahydroitaconitin with potassium permanganate, as well as the ozonolysis of the same substance yielded 2-methylnonanedioic acid. From these and other experimental data including nuclear magnetic resonance spectra, the structural formula of itaconitin and all its derivatives hitherto prepared were conclusively established.
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Toshio Nambara, Motohiko Kato
1965 Volume 13 Issue 1 Pages
78-86
Published: January 25, 1965
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The specificity of the Zimmermann reaction was examined with 38 kinds of 16- and 17-oxosteroids. The influences of environmental situation around oxo group on the reactivities were observed and interpreted in terms of stereochemistry. Of 16-substituted 17-oxosteroids only 16-monohalo derivative showed an exceptional behaviour giving a typical Zimmermann color. By treatment of the colored solution produced from 16α-bromodehydroisoandrosterone, the Zimmermann complex, 3β-hydroxy-16ξ-(2, 4-dinitrophenyl) androst-5-en-17-one, m.p. 186∼188°, was obtained and proved to be identical with that of dehydroisoandrosterone.
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Shin-ichi Sasaki, Shohei Aoyagi, Hong-Yeng Hsii
1965 Volume 13 Issue 1 Pages
87-88
Published: January 25, 1965
Released on J-STAGE: March 31, 2008
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Shun-ichi Yamada, Takayuki Shioiri, Taisuke Itaya, Takeshi Hara, Rei M ...
1965 Volume 13 Issue 1 Pages
88-93
Published: January 25, 1965
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A convenient method for the synthesis of 1-alkyltryptophans is described. The proof of ind. -N-alkylation was obtained from several data. Effect of 1-alkyl substitution of indole was observed on the ultraviolet spectra of 1-alkytryptophans. It was confirmed by debenzylation of L-1-benzyltryptophan in liquid ammonia that no racemization had occurred in the alkylation. 1-Alkyltryptophans were converted to hydrazides via methyl ester hydrochlorides in good yields.
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Yutaka Fujise, Takashi Toda, Sho Ito
1965 Volume 13 Issue 1 Pages
93-95
Published: January 25, 1965
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Morizo Ishidate, Zenzo Tamura, Toshio Kinoshita
1965 Volume 13 Issue 1 Pages
99-101
Published: January 25, 1965
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Yasuo Inoue, Shohei Aoyagi, Koji Nakanishi
1965 Volume 13 Issue 1 Pages
101-104
Published: January 25, 1965
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Yasuo Inubushi, Yoshisuke Tsuda, Takehiro Sano, Ritsuko Nakagawa
1965 Volume 13 Issue 1 Pages
104-105
Published: January 25, 1965
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