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Mineo Saneyoshi, Goro Chihara
1967 Volume 15 Issue 7 Pages
909-914
Published: July 25, 1967
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Several thiocyanato derivatives of purines and their ribonuclesides as potential antineoplastic agents, were prepared by the reaction of mercaptopurines and their ribonucleosides with cyanogen bromide. The reaction of these thiocyanato derivatives were examined with acid, alkali, sodium methoxide and Raney Ni.
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Keiichi Tanikawa, Katsumi Hirano, Kiichi Arakawa
1967 Volume 15 Issue 7 Pages
915-920
Published: July 25, 1967
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The separation of various metal trifluoroacetylacetonates is found to be easier than that of acetylacetonate. Although the separation of acetylacetonate of Cr
3+, Cu
2+, Fe
3+ and other was found to be not possible due to overlapping, it became possible with trifluoroacetylacetonate. The columns using XE-60, that is nitrile sillicone polymer, as a solid phase liquid gave favorable results. As to those which shows short retention time, the use of Daifl oil, namely Trifluorotrichloroethylene, gave a good chromatogram. In the separation of stereoisomers also XE-60 as well as QF-1 facilitated separation.
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Tetsuzo Kato, Hiroshi Yamanaka, Tetsuichi Shibata
1967 Volume 15 Issue 7 Pages
921-924
Published: July 25, 1967
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Claisen and Meyer
2) reported the pyrolysis of acetoacetamide (I) to afford 2, 4-dimethyl-5-oxo-1, 6-dihydro-3-pyridinecarboxamide (II-a), which, on hydrolysis, was converted to the lutidone carboxylic acid (III-a). We re-tested this reaction and found that 3-acetyl-4-amino-6-methyl-2-pyridone (II-b) is the proper structure for the pyrolyzed product and that 3-acetyl-4-hydroxy-6-methyl-2-pyridone (III-b) is the correct one for the hydrolyzed compound.
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Kiichiro Kakemi, Hitoshi Sezaki, Shikifumi Kitazawa
1967 Volume 15 Issue 7 Pages
925-931
Published: July 25, 1967
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Antagonistic effects of PABA on the tuberculostatic activities of synthesized ω-substituted alkyl esters of PAS were examined. It was found that these derivatives were competitively antagonized and their inhibition indices decreased to 0.1 or 0.01 from one of the parent compound, and the correlation between partition coefficients and inhibition indices of these derivatives seems to exist.
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Mamoru Kamiya, Keiichiro Hatano, Takao Kwan
1967 Volume 15 Issue 7 Pages
932-935
Published: July 25, 1967
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Photo-sensitized decomposition of methyl alcohol in the presence of p-benzoquinone has been investigated by electron spin resonance method at a frozen state. Four kinds of ESR spectrum were distinguished ; these were CH
2OH, CHO, CH
3 and probably p-benzosemiquinone radical. Inspection of the developing pattern of these spectra has led to a result that CHO and CH
3 radicals are secondarily produced rather than photoprimarily. The methyl radical was found to be less stable compared with the other radicals. The decay of methyl radical was investigated and found to obey the second order rate law. Photo-sensitized decomposition of ethyl alcohol was investigated additionally.
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Tadakazu Tsuji, Hiroko Momona, Takeo Ueda
1967 Volume 15 Issue 7 Pages
936-943
Published: July 25, 1967
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The hydrochlorides of N
1-benzyl-2-methyl-1, 2-propanediamine (I) and 5-amino-1, 3-dibenzyl-5-methylhexahydropyrimidine (II) were debenzylated by the catalytic hydrogenation under pressure. 2-Methyl-1, 2-propanediamine (III) which obtained from I, was derived to monoguanidine compound. The structure of this compound was concluded to be (2-amino-2-methylpropyl) guanidine from the comparison of the infrared spectra of related compounds. 2-Methyl-1, 2, 3-propanetriamine obtained from II, its starting material II, and other ethylenediamine derivatives were also guanidilated by the action of S-methylisothiourea sulfate.
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Shigeru Kurooka, Kanoo Hosoki, Yoshio Yoshimura
1967 Volume 15 Issue 7 Pages
944-948
Published: July 25, 1967
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It has been confirmed that 3'-
32P-labeled CoA was enzymatically prepared by incubating 3'-dephospho-CoA with
32P-labeled p-nitrophenyl phosphate and cell suspensions of Proteus mirabilis. The formed labeled CoA with a specific radioactivity of 2 μc per mg. was separated from the reaction mixture by an ECTEOLA cellulose column chromatography. The amount of the labeled CoA was determined enzymatically by phosphotransacetylase-hydroxamic acid assay, spectrophotometrically based on the molecular extinction coefficient of CoA, and radiochemically from the known specific radioactivity of
32P-labeled p-nitrophenyl phosphate.
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Shozo Kamiya, Akitada Nakamura
1967 Volume 15 Issue 7 Pages
949-958
Published: July 25, 1967
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The Michael-type addition of maleic and phthalic hydrazide derivatives with an α, β-unsaturated carbonyl compound such as methyl vinyl ketone or acrolein was examined. All of the products were comfirmed to be the N-addition products by comparing their infrared spectra with those of the corresponding O-and N-deuterated compounds. By the Bucherer synthesis these addition products were converted to the corresponding hydantoins from which new, heterocyclic ring-substituted α-amino acids were obtained by hydrolyzing with barium hydroxide. Some of the hydantoins were independently synthesized from 2-amino-2-methyl-4-hydroxybutyric acid via 4-(2-iodoethyl)-4-methylimidazolidine-2, 5-dione.
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Masao Tomita, Hiroshi Furukawa, ShengTeh Lu, S.Morris Kupchan
1967 Volume 15 Issue 7 Pages
959-963
Published: July 25, 1967
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Reinvestigation on the constitution of thalicarpine, previously, isolated from Thalictrum and Hernandia species, was descrived. Ullmann condensation product of L-6'-bromolaudanosine and N-methyllaurotetanine was identified with natural thalicarpine. Accordingly, the revised constitution of thalicarpine was established to have the formula IX.
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Keijiro Samejima, Zenzo Tamura, Morizo Ishidate
1967 Volume 15 Issue 7 Pages
964-975
Published: July 25, 1967
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Biliary metabolites of o-aminoazotoluene (OAT), i. e. 4-amino-3, 2'-dimethylazobenzene, were investigated in rat and identified as N-glucuronide of OAT, N-glucuronide of OAT-derivative whose 2'-methyl group was oxidized hydroxymethyl, conjugates of 4'-hydroxylated OAT with sulfuric acid or glucuronic acid, similar conjugates of 4'-hydroxylated and N-acetylated OAT, and a double conjugate of 4'-hydroxylated OAT with N-glucuronic acid and O-sulfuric acid. The method for determination of OAT-NG, a main metabolite, in which an internal standard substance was adopted to thin-layer chromatography, was examined and gave good results. Similar methods were also examined for determination of other minor metabolites.
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Shigeo Suzuki, Masuko Suzuki, Osamu Sakaguchi
1967 Volume 15 Issue 7 Pages
976-979
Published: July 25, 1967
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Isolation of galactomannan from the culture medium of Trichophyton rubrum by means of Sephadex gel-filtration and ion-exchange chromatography was described. The galactomannan was not precipitated with Fehling's solution, and the ratio of galactose to mannose was 1 : 2.24, and had a positive specific rotation, [α]
18D : +25°.
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Yoshisuke Tsuda, Yoshio Sasaki, Shojiro Uyeo
1967 Volume 15 Issue 7 Pages
980-987
Published: July 25, 1967
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In continuation of our previous paper, the structures of compounds C, D, and E, obtained in minute yields during the Hofmann degradation of O-methyltazettine methine methohydroxide or in better yields by treatment of the methiodide with tert-butoxide under the analogous conditions, were shown to be represented by formulas (VI), (XIV), and (XV), respectively.
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Katsura Morita, Shigeru Kobayashi
1967 Volume 15 Issue 7 Pages
988-993
Published: July 25, 1967
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Lenthionine, an odorous substance, has been isolated from Lentinus edodes (Berk.) Sing and the structure was established as 1, 2, 3, 5, 6-pentathiepane (I). 1, 2, 4, 6-Tetrathiepane (II) and 1, 2, 3, 4, 5, 6-hexathiepane (III) were also isolated from the mushroom in minor quantities. All these cyclic methylene polysulfides were synthesized from simple starting materials. A precursor of lenthionine was isolated in crystalline form and the structure was deduced mainly on the mass spectral studies. A possible mechanism for the formation of lenthionine and its analogs from the precursor was proposed.
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Manabu Hanano
1967 Volume 15 Issue 7 Pages
994-1001
Published: July 25, 1967
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The convolution equation was introduced to estimate a drug release from various dosage forms in the gut. [numerical formula] From the application of the equation, the drug release in vivo F (t) was calculated from comparison of blood level or urinary excertion of drug and/or the metablites between the ingestions of a dosage form, X (t), and the dissolved solution, G (t). The evidence of merits of this method and the deviation of the results from the real value caused by the approximation for numerical calculation were investigated by means of a theoretical model. The actual sulfamethylthiadiazole release from the tablet in human gut was estimated from the urinary excretion by using this calculation method also.
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Hisashi Nogami, Manabu Hanano
1967 Volume 15 Issue 7 Pages
1002-1009
Published: July 25, 1967
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The drug release property from the six commercial sugar coated tablets which contain antipyretic and analgesic igredients were estimated from comparison of the urinary excretions after the oral ingestion of tablets and the dissolved solutions in human. The igredients are sulpyrine, aminopyrine, phenacetin, bucetin, N-acetyl-p-aminophenol, salicylamide and Al-acetylsalicylate. The over-all mean value of the time of fifty per cent drug release in the gut was 1.62 hr. The mean availability was as good as 96.2 per cent. The release rate of Al-acetylsalicylate was slower than the others in statistically significant and also the instances of poor availability of the drug were observed. The merits of the convolution equation method for the estimation of release rate in vivo were demonstrated in the case of the compounded drug.
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Takayuki Shioiri, Kikuo Ishizumi, Shunichi Yamada
1967 Volume 15 Issue 7 Pages
1010-1014
Published: July 25, 1967
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The ultraviolet, infrared and nuclear magnetic resonance spectra of cycloalkan [b] indolones have been investigated. Steric inhibition of resonance is accompanied by a bathochromic and hypochromic shift in the ultraviolet spectra. It was found that the carbonyl stretching frequency of cycloalkan [b] indolones increased as increasing ring size. The nuclear magnetic resonance spectra also showed ring size effect.
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Masako Ohtsuru, Kazuo Tori, Haruyuki Watanabe
1967 Volume 15 Issue 7 Pages
1015-1020
Published: July 25, 1967
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From a number of collected proton magnetic resonance data on various aromatic molecules and their methyl derivatives, it was derived a hypothesis that the methyl substitution effect. upon the signal position of an ortho-proton transmits through the aromatic C=C bond having more double bond character (the larger value of π-bond order) more strongly than through the C=C bond having less double bond character (the smaller value of π-bond order). This rule might be useful in inferring the double bond character of a C=C bond in an aromatic molecule.
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Masashi Tomoda, Masako Kitamura
1967 Volume 15 Issue 7 Pages
1021-1024
Published: July 25, 1967
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The polysaccharides extracted from the seed of Lupinus luteus were fractionated with the chromatography on DEAE-cellulose, and main two fractions obtained were purified by the gel filtration on Sephadex G-50 and G-100. The each of two polysaccharides so obtained was homogeneous on gel filtration and thin-layer electrophoresis. The component carbohydrates of both of them were D-galactose, L-arabinose, D-galacturonic acid, D-xylose and L-rhamnose, and the molar ratios of these sugars in the two polysaccharides were 15 : 10 : 6 : 2 : 2 in one, and 6 : 4 : 3 : 1 : 1 in the other.
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Yukichi Kishida, Tetsuo Hiraoka, Junya Ide, Atsusuke Terada, Norio Nak ...
1967 Volume 15 Issue 7 Pages
1025-1031
Published: July 25, 1967
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Ibotenic acid (α-amino-3-hydroxy-5-isoxazoleacetic acid monohydrate) (I), a flycidal amino acid isolated from Amanitae fungi, was synthesized. The reaction of ethyl 4, 4-diethoxytetrolate (V) with hydroxylamine in the presence of alkali gave 3-hydroxy-5-isoxazolecarboxaldehyde diethyl acetal (VI), which was hydrolyzed with 50% AcOH to the corresponding 3-hydroxy-5-isoxazolecarboxaldehyde (II). Strecker or Bucherer reaction of II followed by alkaline hydrolysis afforded I, which was identical with the natural ibotenic acid.
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Shoji Hara, Michiko Miyaki
1967 Volume 15 Issue 7 Pages
1032-1035
Published: July 25, 1967
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The quantitative relationship between chromatographic mobility and steroid structure has been investigated. The group Rm increments were calculated from the mean Rf values of a number of steroid hormones, sapogenins, and bile acids.
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Shoji Hara, Kunio Mibe
1967 Volume 15 Issue 7 Pages
1036-1040
Published: July 25, 1967
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A systematic and simultaneous analysis by thin-layer chromatography was made on thirty seven steroids used as pharmaceuticals, and the mobility and specific coloration of each compound were examined. Parameters were calculated for substituents and assumptions were made on the mechanism of the adsorption of steroid compounds.
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Shoji Hara, Tadashi Watabe, Yoshimasa Ike, Nobuo Ikekawa
1967 Volume 15 Issue 7 Pages
1041-1044
Published: July 25, 1967
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Systematic analyses were carried out by gas chromatography on about forty C
19 and C
18 synthetic steroids. A correlation between their retention time and molecular structure was examined and parameters were calculated for their functional groups.
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Shoshichiro Kimoto, Masao Okamoto
1967 Volume 15 Issue 7 Pages
1045-1051
Published: July 25, 1967
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Hidetaka Yuki, Torahiko Kishikawa, Yasuo Tohira, Kazuhiro Watanabe
1967 Volume 15 Issue 7 Pages
1052-1055
Published: July 25, 1967
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Tokuji Suzuki, Yuichi Tanimura
1967 Volume 15 Issue 7 Pages
1055-1058
Published: July 25, 1967
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Tetsuya Suga, Isao Ohata, Hiroshi Kumaoka, Masuo Akagi
1967 Volume 15 Issue 7 Pages
1059-1064
Published: July 25, 1967
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Bunji Shimizu, Michiko Miyaki
1967 Volume 15 Issue 7 Pages
1066-1068
Published: July 25, 1967
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Takao Maki, Setsuzo Tejima
1967 Volume 15 Issue 7 Pages
1069-1071
Published: July 25, 1967
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Morio Kishi, Tadahiro Kato, Yoshio Kitahara
1967 Volume 15 Issue 7 Pages
1071-1073
Published: July 25, 1967
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Yoshisuke Tsuda, Masao Hattori
1967 Volume 15 Issue 7 Pages
1073-1075
Published: July 25, 1967
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Tatsuo Yamauchi, Yukihiro Shoyama, Hanichiro Aramaki, Tomoko Azuma, It ...
1967 Volume 15 Issue 7 Pages
1075-1076
Published: July 25, 1967
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Mikio Honjo, Yoshiyasu Furukawa, Masao Nishikawa, Kazuhide Kamiya, Yos ...
1967 Volume 15 Issue 7 Pages
1076-1079
Published: July 25, 1967
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Akinori Kubo, Shinichiro Sakai, Sachiko Yamada, Ichiro Yokoe, Chikara ...
1967 Volume 15 Issue 7 Pages
1079-1082
Published: July 25, 1967
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