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Morio Ikehara, Hiroshi Tada, Kei Muneyama
1965 Volume 13 Issue 6 Pages
639-642
Published: June 25, 1965
Released on J-STAGE: March 31, 2008
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8-Bromoguanosine was directly obtained from guanosine by means of dioxane-bromine bromination. Mesylation of 8-bromoguanosine gave 2', 5'-di-O-mesyl derivative, which was converted to 2'-O-mesyl-8-mercapto-5', 8-anhydroguanosine by the treatment with thiourea. Desulfurization of 5', 8-cyclonucleoside and subsequent removal of mesyl group gave 5'-deoxyguanosine. Acid hydrolysis of 2'-O-mesyl-5'-deoxyguanosine gave 2'-O-mesyl-5'-deoxyribose.
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Sataro Imado, Motoo Shiro, Zen-ichi Horii
1965 Volume 13 Issue 6 Pages
643-651
Published: June 25, 1965
Released on J-STAGE: March 31, 2008
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X-ray crystal structure analysis has been made on the securinine hydrobromide dihydrate, which is monoclinic, with two formula units in a cell of dimensions : α=7.71Å, b=14.83Å, C=7.04Å, and γ=112.13°. The space group is P2
1. The determination of the atomic parameters was carried out by the generalized projection methods. The conclusions may be summed up as follows : The piperidine ring has a skewed boat form, and the diene part is not co-planar. A dihedral angle of about 10°has been found between the plane passing through C2-, C3-, and C3a-atoms and the one involving C3a-, C4-, and C5-atoms. Discussion has been made on the location of the lone electron pair on the nitrogen atom in the free base.
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Zen-ichi Horii, Takefumi Momose, Yasumitsu Tamura
1965 Volume 13 Issue 6 Pages
651-662
Published: June 25, 1965
Released on J-STAGE: March 31, 2008
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As a part of the investigation on the synthesis of η-pyrromycinone (I), methyl 2-ethyl-5-hydroxy-1-naphthoate (II, R=OH) was synthesized by a series of reactions indicated in Chart 1 and 2. The stereochemistries of the tetralone derivatives obtained as preparative intermediates were discussed from the chemical and nuclear magnetic spectral evidences.
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Issei Iwai, Junya Ide
1965 Volume 13 Issue 6 Pages
663-672
Published: June 25, 1965
Released on J-STAGE: March 31, 2008
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Treatment of diphenylacetylene with dimethylsulfinyl carbanion in dimethyl sulfoxide at room temperature gave two stereoisomeric compounds : trans-3-methylsulfinyl-1, 2-diphenyl-1-propene (I-a) and cis-3-methylsulfinyl-1, 2-diphenyl-1-propene (I-b) at a ratio of 88.5% and 11.5% respectively, which were confirmed by ultraviolet, infrared, nuclear magnetic resonance spectra and elemental analyses. Analogously trans-1-methylsulfinyl-2, 5-diphenyl-2-penten-4-yne (III-a) and cis-1-methylsulfinyl-3, 1-diphenyl-2-pentin-4-yne (III-b) at a ratio of 84% and 16% respectively, were obtained from 1, 4-diphenyl-1, 3-butadiyne and the carbanion. Treatment of the trans-sulfoxide (III-a) with the carbanion at room temperature gave a cis-trans mixture at a ratio of 84% of trans and 16% of cis isomer. Furthermore, 2, 3-diphenyl-1, 3-butadiene (II) was given from diphenylacetylene and methylsulfinyl carbanion at relatively high temperature.The proposed reaction mechanism affording II would probably involve double addition of the anion to triple bond followed by elimination of two moles of methanesulfinic acid.
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Yoshinobu Hirasaka, Isao Matsunaga
1965 Volume 13 Issue 6 Pages
672-676
Published: June 25, 1965
Released on J-STAGE: March 31, 2008
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The two α (1, 4) linked disaccharides containing the reducing glucuronic acid residue (GU and UU) were found to tend to lactonize in aqueous solution. 4-O-(α-D-Glucopyranosyl)-D-glucurono-6, 1-lactone (X) and 4-O-(α-D-glucopyranosiduronyl)-D-glucurono-6, 1-lactone (XI) were purified by chromatographic separation and identified by methylation with silver oxide and methyl iodide followed by acid hydrolysis. Moreover hepta-O-acetyl-4-O-(α-D-glucopyranosyl)-D-glucurono-6, 1-lactone (XII) and penta-O-acetyl-4-O-(α-D-glucopyranosiduronyl)-D-glucurono-6, 1-lactone (XIII) were obtained from hepta-O-acetyl-4-O-(α-D-glucopyranosyl)-D-glucuronic acid (V) and hexa-O-acetyl-4-O-(α-D-glucopyranosiduronyl)-D-glucuronic acid (VI), respectively.
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Yoshinobu Hirasaka, Kenji Umemoto, Mitsuo Sukegawa, Isao Matsunaga
1965 Volume 13 Issue 6 Pages
677-680
Published: June 25, 1965
Released on J-STAGE: March 31, 2008
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The equilibrium relation among D-glucosaccharic acid and its lactones (nemely 1, 4-and 6, 3-monolactones and 1, 4 : 6, 3-dilactone) in aqueous solution was investigated. It was found that the dilactone was detectable only at elevated temperature, and that the amount of the 1, 4-lactone in equilibrium was almost indifferent to temperature.
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Akira Takamizawa, Kentaro Hirai
1965 Volume 13 Issue 6 Pages
681-686
Published: June 25, 1965
Released on J-STAGE: March 31, 2008
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The correlation was seen between the positions of NH groups and the NH stretching pattern in infrared spectra of 1-substituted tetrahydropyrimidine derivatives and 3-substituted compounds. The measurement of the infrared spectra of these compounds in Nujol mull is useful to assign their structures. Differences in the reactivities between 1-NH and 3-NH groups were recognized by several reactions. Addition of dihydropyran to I occurred at 3-NH and the Michaeltype addition reaction proceeded giving N-1-adducts and N-1, 3-di-adducts.
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Ken'ichi Takeda, Taichiro Komeno, Norio Tokutake, Yoshiko Kanematsu
1965 Volume 13 Issue 6 Pages
687-691
Published: June 25, 1965
Released on J-STAGE: March 31, 2008
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Some estratrienones having a sulfur atom at C-16 were prepared by substitution of 16α-bromo-17-ketosteroids with sulfur nucleophiles.
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Ken'ichi Takeda, Ariyoshi Shimaoka, Mitsutaka Iwasaki, Hitoshi Minato
1965 Volume 13 Issue 6 Pages
691-694
Published: June 25, 1965
Released on J-STAGE: March 31, 2008
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The steroidal constituents of Chionographis japonica MAXIM. were investigated, and four steroidal sapogenins, diosgenin (I), bethogenin (IIa), pennogenin (III) and kryptogenin (Va), were isolated. Moreover, chiogralactone and four unknown compounds were obtained as compounds other than steroidal sapogenins.
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Masao Tomita, Toshiro Ibuka, Yasuo Inubushi, Kyoji Takeda
1965 Volume 13 Issue 6 Pages
695-704
Published: June 25, 1965
Released on J-STAGE: March 31, 2008
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The structure of metaphanine was examined and the partial structure (Ic) was presented.
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Masao Tomita, Toshiro Ibuka, Yasuo Inubushi, Kyoji Takeda
1965 Volume 13 Issue 6 Pages
704-712
Published: June 25, 1965
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Metaphanine was shown to be an alkaloid derived from a new ring system "hasubanan." Degradative and spectroscopic evidence established metaphanine as I. The absolute configuration of this alkaloid was established as shown by the perspective formula (XXI).
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Ikuo Suzuki, Toshiaki Nakashima, Natsuko Nagasawa
1965 Volume 13 Issue 6 Pages
713-716
Published: June 25, 1965
Released on J-STAGE: March 31, 2008
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The oxidation of 5-nitrocinnoline (I) with hydrogen peroxide in acetic acid, and with persulfuric acid in sulfuric acid afforded 5-nitrocinnoline 1-oxide (II), 5-nitrocinnoline 2-oxide (III), and 4-nitroindazole (IV). The Oxidation of 8-nitrocinnoline (V) with hydrogen peroxide in acetic acid, with hydrogen peroxide, with phthalic monoperacid, with hydrogen peroxide in 10% sulfuric acid, and with persulfuric acid in sulfuric acid afforded 8-nitrocinnoline 2-oxide (VI), 7-nitroindazole (VII), and 8-nitro-4-cinnolinol (VIII). On the other hand, the oxidation of V with chromic acid in acetic acid gave only VIII with recovery of V.
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Hitoshi Minato, Makoto Ishikawa, Tohru Nagasaki
1965 Volume 13 Issue 6 Pages
717-720
Published: June 25, 1965
Released on J-STAGE: March 31, 2008
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A microtechnique for dehydrogenation of some perhydroazulene and -naphthalene derivatives was developed, and the optimum reaction conditions were discussed.
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Kyosuke Tsuda, Yoshihiro Sato, Sayoko Tanaka, Hideaki Higashikuze, Nob ...
1965 Volume 13 Issue 6 Pages
720-723
Published: June 25, 1965
Released on J-STAGE: March 31, 2008
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The separation of twenty-eight kinds of standard bile acids by gas liquid chromatography using QF-1, NGS, CNSi, SE-30 or SE-52 packing is discussed.
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Haruhiko Yamamoto, Makoto O'hara, Takao Kwan
1965 Volume 13 Issue 6 Pages
724-730
Published: June 25, 1965
Released on J-STAGE: March 31, 2008
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The selectivity for the ring hydrogenation of aniline was investigated by the gas chromatographic pulse technique on the acid or base supported nickel, cobalt and iron catalyst respectively. Following results were obtained : 1) The selectivity for the ring hydrogenation was best on cobalt among three metals. 2) The calcium oxide supported catalyst generally suppressed the hydrogenolysis at the carbon-nitrogen bond giving rise to the efficient hydrogenation of the ring. 3) The silica-alumina support enhanced the formation of secondary amines. The selectivity was discussed on the basis of the interaction of amine with the surface and possible mechanism was presented.
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Yukio Kuroiwa, Ken-ichiro Minegishi, Seiichi Okui
1965 Volume 13 Issue 6 Pages
731-734
Published: June 25, 1965
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It is very convenient to use methylbarbital as substrate in order to check the pheno-barbital-effect, and on the other hand, meperidine is useful to measure the degree of inhibition in the enzyme activity by narcotics such as morphine etc. It was recognized that the repeated administration of morphine to rats caused gradually depression of detoxicating enzyme activity in demethylation of narcotics, but did not affect on the incorporation of
14C-amino acids into rat liver protein.
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WernerW. Zorbach, W. Buhler, Seitaro Saeki
1965 Volume 13 Issue 6 Pages
735-736
Published: June 25, 1965
Released on J-STAGE: March 31, 2008
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Zen-ichi Horii, Takefumi Momose, Yasumitsu Tamura
1965 Volume 13 Issue 6 Pages
737-740
Published: June 25, 1965
Released on J-STAGE: March 31, 2008
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The Friedel-Crafts condensation of 3, 6-dimethoxyphthalic anhydride (II) with methyl 2-ethyl-5-hydroxy-1-naphthoate (III) gave 2-ethyl-5-hydroxy-6-(2-carboxy-3, 6-dimethoxy-benzoyl)-1-naphthoate (IV), a key intermediate for the synthesis of η-pyrromycinone (I, R=H). An attempt to cyclize IV to η-pyrromycinone dimethyl ether (I, R=CH
3), however, resulted in formation of 9-ethyl-1, 6-dihydroxy-4-methoxynaphthacenequinone (V). The Structure of V was confirmed by alternative synthesis.
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Zen-ichi Horii, Takefumi Momose, Yasumitsu Tamura
1965 Volume 13 Issue 6 Pages
740-744
Published: June 25, 1965
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1, 11-Dimethoxy-5(12H)-naphthacenone derivatives were synthesized, and the successful conversion of them into the corresponding 4, 6-dimethoxynaphthacenequinone derivatives by chromium trioxide oxidation was investigated.
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Masayuki Ishikawa, Sachiko Yamada, Chikara Kaneko
1965 Volume 13 Issue 6 Pages
747-749
Published: June 25, 1965
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Yasuo Inubushi, Yoshisuke Tsuda, Takehiro Sano
1965 Volume 13 Issue 6 Pages
750-751
Published: June 25, 1965
Released on J-STAGE: March 31, 2008
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Shun-ichi Yamada, Shiro Terashima, Kazuo Achiwa
1965 Volume 13 Issue 6 Pages
751-753
Published: June 25, 1965
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Hidesuke Iwasaki, Takaaki Kamiya, Osamu Oka, Jisaburo Ueyanagi
1965 Volume 13 Issue 6 Pages
753-758
Published: June 25, 1965
Released on J-STAGE: March 31, 2008
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