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Yoshio Sasaki, Miyoko Suzuki, Akiko Shimazu, Atsuko Misaki
1967 Volume 15 Issue 8 Pages
1083-1087
Published: August 25, 1967
Released on J-STAGE: March 31, 2008
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The reliability and limitation on the simple sum rule of the shielding parameters in polysubstituted benzene series have been discussed and the ring proton chemical shifts for several systems have been estimated from the above parameters.
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Ikuo Suzuki, Masahiro Nakadate, Toshiaki Nakashima, Natsuko Nagasawa
1967 Volume 15 Issue 8 Pages
1088-1094
Published: August 25, 1967
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Cinnoline dioxide (IV) and indazole (V) were obtained in addition to the monoxides on oxidation of cinnoline (I) with hydrogen peroxide in acetic acid. The structure of IV was confirmed by chemical and physico-chemical methods of UV, IR and NMR spectrometry and by polarographic reduction.
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Hikaru Ozawa, Kazutaka Momose, Shinsaku Natori
1967 Volume 15 Issue 8 Pages
1095-1100
Published: August 25, 1967
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Effects of naturally occurring benzoquinone derivatives on rat liver mitochondrial respiration were examined manometrically and polarographically comparing with ubiquinone-0. Dihydroxythymoquinone, helicobasidin, and dihydroperezone were found to show significant effect on the respiration. At the concentration of 1.0×10
-5M, dihydroxythymoquinone eliminated the State-3 respiration completely and the for 50% inhibition of the State-3 respiration it required the concentration of 3.2×10
-6M. Helicobasidin was an uncoupler and dihydroperezone showed both an uncoupling action on State-4 respiration and an inhibitory action of State-3 respiration. The other benzoquinone derivatives examined did not show any significant effects on mitochondrial respiration.
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Hidetaka Yuki, Tadahiro Yamamoto, Yasuo Tohira, Bunya Aoki, Tokio Kano ...
1967 Volume 15 Issue 8 Pages
1101-1106
Published: August 25, 1967
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N-and 2-substituted maleimides were synthesized as antiviral agents. Though all were negative against Adenovirus type 5 and Newcastle disease virus, some compounds were found to be active against certain bacteria and fungi.
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Hidetaka Yuki, Yasuo Tohira, Bunya Aoki, Tokio Kano, Shinichi Takama, ...
1967 Volume 15 Issue 8 Pages
1107-1111
Published: August 25, 1967
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Tenuazonic acid derivatives were synthesized from amino acid esters by N-acetoacetylation with diketene followed by cyclization with sodium alkoxides. Some L-amino acid produced a small amount of DL-compounds in this process. N-Acetoacetyl group of diethyl aspartate cyclized to the α-ester group to form five-membered ring compound selectively. These compounds were condensed with carbonyl reagents.
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Misako Tachibana, Shohei Sawaki, Yutaka Kawazoe
1967 Volume 15 Issue 8 Pages
1112-1119
Published: August 25, 1967
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The polarographic reduction potentials (NO
2→NHOH) were measured of 35 kinds of nitroquinoline derivatives. Discussions were made on the E
1/2 values in connection with their chemical structures.
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Seikichi Suzuki, Fumihiko Sano, Hidetada Yuki
1967 Volume 15 Issue 8 Pages
1120-1122
Published: August 25, 1967
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Antiviral activity of tenuazonic acid derivatives against adenovirus type 5 was examined. Some compounds showed the significant chemotherapeutic indexes. This antiviral activity was not antagonized by the amino acid from which the test compounds were derived.
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Hidetaka Yuki, Torahiko Kishikawa, Yasuo Tohira, Seikichi Suzuki, Fumi ...
1967 Volume 15 Issue 8 Pages
1123-1128
Published: August 25, 1967
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N-chloro compounds were synthesized and their virus inactivating activity and probable mechanism of the action were investigated. It is likely that the N-chloro compounds oxidize the sulfhydryl groups of the viral protein coat to form disulfide, disulfoxide, and sulfinic acid resulting in inactivation of the virus. This action is nonspecific and irreversible, and is lost in the presence of serum proteins.
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Haruhiko Yamamoto, Hiroyuki Horiguti, Kunio Noda, Takao Kwan
1967 Volume 15 Issue 8 Pages
1129-1137
Published: August 25, 1967
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o-, m-, p-xylene and their tetrahydro derivatives were hydrogenated by a reduced nickel catalyst over the temperature range 150∼250°to investigate the mechanism of the stereoselective formation of cis and trans isomer in vapor phase. The selectivity for the formation of trans isomer was the greatest with p-xylene and the smallest with m-xylene. More than 50% trans isomer was produced with p- and o-xylene but not with m-xylene over the entire temperature range investigated. A similar result was obtained also for the hydrogenation of dimethylcyclohexenes. On the basis of these findings, the Horiuti-Polanyi-Siegel mechanism, as shown schematically in Fig. 6, was discussed taking into consideration various adsorbed types for the half-hydrogenated state. It was shown that the mechanism will meet some difficulties to account for the experimental results. On the other hand, the trans addition of hydrogen to π-allylic adsorbed species giving rise to trans isomer was considered to occur in particular at higher temperatures.
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Akio Hoshi, Reiko Yanai, Kazuo Kuretani
1967 Volume 15 Issue 8 Pages
1138-1144
Published: August 25, 1967
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The effect of terephthalic acid (TPA) upon sulfadimethoxine contents in blood plasma was studied. The drug contents in blood plasma were increased by TPA feeding both in the rat and in the rabbit. The maximum contents of the drug in blood plasma were not so affected. However, 24 and 48 hr. after a single administration, they showed significant increases from that of the control. The drug excretion amounts in the urine of the TPA group was lower than those of the control and the plasma half-life of the drug was elongated by TPA administration, about 1.5 times in the rat and 1.9 times in the rabbit. Absorption of the drug through the gastrointestinal tract decreased with TPA administration and high contents of TPA might have a hindering effect on drug absorption from the small intestine. The contests of N
4-acetate of the drug were increased by TPA administration. This increasing effect of TPA upon sulfadimethoxine seems to be concerned with excretion from the kidney. As a result, it is supposed that the plasma half-life of the drug is elongated.
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Akira Tahara, Kenichi Hirao
1967 Volume 15 Issue 8 Pages
1145-1152
Published: August 25, 1967
Released on J-STAGE: March 31, 2008
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The configuration and conformation of 10β- and 10α-enantio-deoxypodocarpic acid type isomer and the corresponding lactone were discussed by their NMR spectrum analysis. The analysis was performed especially on the ABX type proton system as observed between 9-methylene protons and 10-proton.
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Yasuo Inubushi, Yoshisuke Tsuda, Takehiro Sano, Takeshi Konita, Sachik ...
1967 Volume 15 Issue 8 Pages
1153-1168
Published: August 25, 1967
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Retropinacol rearrangement of serratenediol established that either terminal ring of this triterpenoid has the partial structure (A). The accumulated chemical and spectroscopic evidences have been summarized in the structure and stereochemistry (1__=) containing sevenmembered ring for serratenediol, which was confirmed by further degradation into a tricyclic ketone (4__=7__=). The synthesis of this key product has now been achieved. The manner of acid isomerization of serratene derivatives has been also clarified. Serratenediol monoacetate, a minor triterpenoid constituent of Lycopodium serratum, was also established as (3__=), based on ORD examination of various ketonic derivatives.
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Masaaki Horiguchi
1967 Volume 15 Issue 8 Pages
1169-1171
Published: August 25, 1967
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Gas liquid chromatography was applied successfully to the separation of a mixture of five quinolizidine derivatives, the reduction products of quinolizinium bromide with sodium borohydride in water. Separation of a mixture of the reduction products and 1, 9α-dehydro-quinolizidine (IV) was reexamined using the same kinds of columns. Of these various liquid phases, DEGS was found the most effective for the complete separation in both the cases.
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Genzo Okusa, Shozo Kamiya, Takanobu Itai
1967 Volume 15 Issue 8 Pages
1172-1177
Published: August 25, 1967
Released on J-STAGE: March 31, 2008
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The Mannich reaction of 3-pyridazinol 1-oxide using morpholine, piperidine, or dimethylamine gave the corresponding 6-alkylaminomethyl-3-pyridazinol 1-oxides which were also synthesized from 3-methoxy-6-chloromethylpyridazine.
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Akira Takamizawa, Yoshio Hamashima, Yoshiro Sato, Hisao Sato
1967 Volume 15 Issue 8 Pages
1178-1182
Published: August 25, 1967
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3-(2-Hydroxy-and 2-acetoxy) ethyl-1, 4, 9-trimethyl-1, 6-dihydropyrimido [4', 5'-4, 5] pyrimido-[2, 3-c] [1, 4] thiazine (IIIb and IVb) were obtained by the reaction of thiamine (I) and diethyl acetylphosphonate (IIb). Alkaline hydrolysis of IIIb or IVb gave 2-methyl-4-(2-methyl-4-amino-5-pyrimidinyl)-methyl-5-methyl-6-(2-hydroxy) ethyl-2H-1, 4-thiazin-3 (4H)-one (Vb), which was decomposed to give VIIb by conc. HCl. The structures of IVb and VIIb were confirmed by the synthetic method.
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Akira Takamizawa, Yoshiro Sato, Hisao Sato
1967 Volume 15 Issue 8 Pages
1183-1187
Published: August 25, 1967
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Several kinds of dialkyl acylphosphonate (IIIa∼d, Va∼d) were synthesized and reacted with thiamine to give 1, 6-dihydropyrimido [4', 5'-4, 5] pyrimido [2, 3-c] [1, 4] thiazine derevatives (XIIA, B, XIIIA, B). Methyl phenylacylphosphinate also gave same result.
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Seigoro Hayashi, Mitsuru Furukawa, Junko Yamamoto, Kunihiro Niigata
1967 Volume 15 Issue 8 Pages
1188-1192
Published: August 25, 1967
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The reactions of benzyl benzene or p-toluenethiosulfonate with active methylene compounds were studied to elucidate the mechanism of anti-tumor activity of the analogous pentamethylene bismethanethiosulfonate with the expectation that any alkylation might occur. It was found that benzene or p-toluenethiosulfonate did not benzylate the active methylene compounds but one or two benzylthio groups were introduced. In the cases of less active methylene compounds, the reaction of thiosulfonates themselves occurred.
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Yoshio Ueno, Shoji Takemura, Yoshiko Ando, Hiromi Terauchi
1967 Volume 15 Issue 8 Pages
1193-1197
Published: August 25, 1967
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Reaction between N, N-dihalobenzenesulfonamide (I) and cyclohexene (II) was studied. Addition products, DL-cis-and DL-trans-2-halo-1-benzenesulfonamidocyclohexanes (III and IV), and by-products, DL-trans-1, 2-dihalocyclohexane (V), 1, 3-cyclohexadiene (VI), 1-cyclohexen-3-one (VIII) and benzenesulfonamide (VII) were isolated and identified from the reaction mixture. A presumption on this reaction was also drawn.
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Yoshio Ueno, Shoji Takemura, Yoshiko Ando, Hiromi Terauchi
1967 Volume 15 Issue 8 Pages
1198-1203
Published: August 25, 1967
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In order to examine the mode of reaction of N, N-dihalobenzenesulfonamide (I) with cyclohexene (II), the assumed intermediate, DL-trans-2, N-dibromo-1-benzenesulfonamidocy-clohexane (X), was synthesized and the formation of it in the pathway of the reaction of the bromo analog of I with II was proved. Comparing the behavior of N-bromo-N-methyl-benzenesulfonamide (XI) with that of X, the reaction of XI with II was examined, which afforded trans-1, 2-dibromocyclohexane (V), 1, 3-cyclohexadiene (VI), and 1-bromocyclohexene (XII). On the basis of these facts, the mechanism of the reaction of I with II was discussed.
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Michiya Kimura, Masahiko Tohma, Itsuo Yoshizawa
1967 Volume 15 Issue 8 Pages
1204-1211
Published: August 25, 1967
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Convallagenin-A (I) was isolated from the flowers of Convallaria keisukei MIQ. and was shown to be a new 25L, 1, 3, 5-trihydroxyspirostane due to the conversion of it to ⊿
1, 4-tigogenone (XII). All of the hydroxyl groups in I were indicated to have β-configuration as a result of forming the 1, 5-carbonate (XIII), the 3, 5-carbonate (XIX), and the orthoester (XX). The chemical structure of convallagenin-A (I) was thus elucidated as 25L, 5β-spirostan-1β, 3β, 5β-triol.
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Kenji Suzuki, Takashi Abiko
1967 Volume 15 Issue 8 Pages
1212-1218
Published: August 25, 1967
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The three analogs of bradykinin are described in which L-proline residue in 3-position of 6-glycine-bradykinin is substituted for sarcosine, glycine, and L-alanine residue respectively. 3-Glycine-bradykinin and its O-acetyl compound are also described. The biological activity of the five analogs is compared with that of bradykinin on an isolated guinea pig ileum.
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Kunihiro Nakajima
1967 Volume 15 Issue 8 Pages
1219-1224
Published: August 25, 1967
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1) Purified samples of polymyxin group antibiotics were shown to be remarkable antimicrobial agents as colistin against E. coli. 2) Removal of the C
9-fatty acid from the colistin molecule resulted in the decrease of the activity. 3) The side chain moiety itself showed no antimicrobial activity. 4) The cyclic peptide moiety showed an antimicrobial activity although it was less active than the parent antibiotic. These results indicate that the "active"structure responsible for the antimicrobial activity is the"cyclic peptide moiety"in colistin molecule.
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Yutaka Kawazoe, Masako Ohnishi, Yuko Yoshioka
1967 Volume 15 Issue 8 Pages
1225-1231
Published: August 25, 1967
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Hydrogen-deuterium exchange of α-hydrogens of the side-chain alkyl groups substituted in pyridine, quinoline, isoquinoline, their N-oxides and N-alkyl halides were carried out by heating their D
2O solutions containing sodium hydroxide or sodium carbonate. Exchange reactivities of these hydrogens were discussed in term of the electronic effect of the nitrogen function in these heteroaromatic rings.
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Toshio Nambara, Kazuhiro Imai
1967 Volume 15 Issue 8 Pages
1232-1238
Published: August 25, 1967
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Syntheses of estriol glucosiduronic acids were carried out employing Koenigs-Knorr reaction. Of these three 16- and 17-glucuronides were prepared from estrone 3-benzyl ether, and 3-isomer from estriol 16, 17-diacetate as shown in Chart 1. All the glucuronides thus obtained underwent hydrolysis with beef liver β-glucuronidase to furnish estriol and glucuronic acid.
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Michiya Kimura, Toshihiro Nishina
1967 Volume 15 Issue 8 Pages
1239-1242
Published: August 25, 1967
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Michiya Kimura, Toshihiro Nishina
1967 Volume 15 Issue 8 Pages
1242-1246
Published: August 25, 1967
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Tadashi Sasaki, Ken Kanematsu
1967 Volume 15 Issue 8 Pages
1247-1250
Published: August 25, 1967
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Isao Kitagawa, Tadashi Nishimura, Masazumi Takei, Itiro Yosioka
1967 Volume 15 Issue 8 Pages
1254-1256
Published: August 25, 1967
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Yo Isogai, Toshihiko Okamoto, Yasuo Komoda
1967 Volume 15 Issue 8 Pages
1256-1257
Published: August 25, 1967
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Hiroaki Nomura, Ikuo Suhara, Norihiro Uno
1967 Volume 15 Issue 8 Pages
1258-1260
Published: August 25, 1967
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Morio Ikehara, Masakatsu Kaneko
1967 Volume 15 Issue 8 Pages
1261-1262
Published: August 25, 1967
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