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二宮 康行, 山田 洋資, 鬼塚 光子, 田中 雄四郎, 前田 津留美, 丸山 博巳
1980 年 28 巻 9 号 p.
2553-2564
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
Four assay systems, i. e. membrane stabilization, inhibition of protein denaturation, and inhibition of collagen- and ADP-induced platelet aggregation, were examined for possible use as in vitro anti-inflammatory screening probes applicable to microbial metabolites. All these systems were simple and reasonably selective for known platelet anti-aggregants or non-steroidal anti-inflammatory agents. As regards sensitivity, detection should be possible at levels of several to several hundred μg/ml for an indomethacin class substance existing in the broth ; such concentrations are attainable in the broth in the case of useful antibiotic production. Each system was hardly disturbed by medium components in the broth and the procedures were successfully applied to actinomycetes cultures. Upon examination of typical non-steroidal anti-inflammatory drugs to determine their effects on these systems, it was found that they could be classified into four distinct types in terms of their mode of action. The correlation of these effects with results in several in vivo models is discussed. Furthermore, the effects of various antibiotics including several types of ionophores on these probes were thoroughly studied.
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今泉 宏之, 南部 直樹, 永井 恒司
1980 年 28 巻 9 号 p.
2565-2569
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
An X-ray diffraction method for determination of the degree of crystallinity of indomethacin was established, and the transition rate of indomethacin from amorphous to crystalline form was investigated. The transition of the amorphous form to crystalline form at 20°, 30°and 40°followed first-order kinetics and the Arrhenius plot showed good linearity. The amorphous form was shown to change to form I at 100% relative humidity (RH), to form I or II at 89% RH and to form I at 79% and 69% RH at 30°. The transition rate of the amorphous form to form II at 100% RH was larger than that at 89% RH. A good linear relation was observed between the maximum amount of water absorbed (log scale) and the degree of crystallinity at 100% or 89% RH at 30°. The dissolution rate of the amorphous form was higher than those of forms I and II. The amorphous form showed better tablet-forming properties than the crystalline form.
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木村 良平, 松井 静雄, 伊藤 聡, 相本 太刀夫, 村田 敏郎
1980 年 28 巻 9 号 p.
2570-2579
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
The central actions of maltol (2-methylpyromeconic acid, II), previously isolated from the extract of Passiflora incarnata, and its analogs were studied in mice. 2-Butyl-and 2-isobutylpyromeconic acid (IVd) were the most potent depressants of pentetrazoleinduced convulsion among the 2-alkylpyromeconic acids tested. The effect of 2-(1-hydroxy-isobutyl)pyromeconic acid (Vd) was more potent than that of IVd. Methylation on the 3-hydroxyl group of II or replacement of the O atom of the 4-pyrone ring with =NH did not alter the effect on pentetrazole-induced convulsion. Both IVd and Vd also showed depressing effects on the convulsion induced by strychnine or picrotoxin but did not affect the convulsion induced by caffeine. The anticonvulsive effects of IVd and Vd on the maximal electroshock seizure were less potent than that of 2-ethylpyromeconic acid (III). II, III, IVd and Vd depressed spontaneous motor activity, and III and Vd prolonged the hexobarbital-induced sleeping time. The brain levels of these four compounds after subcutaneous injection in mice were not related to their lipid solubilities.
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窪田 実, 長瀬 脩, 天野 博夫, 高木 博司, 矢島 治明
1980 年 28 巻 9 号 p.
2580-2586
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
Eight Met- and Leu-enkephalin analogs substituted with L- or D-Arg at position 2 were synthesized using N
G-mesitylene-2-sulfonylarginine. Among them, H-Tyr-D-Arg-Gly-Phe-Met-OH was found to possess an analgesic effect 2.4 times higher than that of morphine on a molar basis, when injected intracisternally. This compound was also found to produce analgesia when administered intravenously.
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石川 文義
1980 年 28 巻 9 号 p.
2587-2592
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
The synthesis and characterization of tricyclic guanidinium salts and their reduced polycyclic trisaminomethane derivatives are described. N-ω-Chloroalkyl bicyclic guanidines (3) readily gave tricyclic guanidinium salt (4) in a neutral medium. Treatment of the compounds 4 with anion exchange resin caused facile ring cleavage to yield various macrocyclic compounds 6-9. The compounds 6-9 reverted to the parent tricyclic guanidinium salts in acidic and basic media as a result of transannular interactions. The guanidinium salts 4 were reduced with sodium borohydride to polycyclic trisaminomethane derivatives (11). The structures of 6-9 and 11 are proposed on the basis of the spectral data.
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湯川 栄二, 香野 敬喜, 小野 行雄, 上田 陽
1980 年 28 巻 9 号 p.
2593-2601
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
A quantum chemical method for prediction of the specific bond of an aromatic hydrocarbon at which hydroxylation will occur most easily in liver microsomes is presented. The interaction energy changes of a binary system composed of an aromatic hydrocarbon and O
2 caused by changes of the mutual spatial arrangement between the hydrocarbon and O
2 were calculated by the CNDO/2 method. This method was applied to the hydroxylations of naphthalene, anthracene, phenanthrene, acenaphthylene, indene and 1, 2-dihydronaphthalene. In all cases, the theoretical predictions were found to coincide very well with the reported experimental results.
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土屋 隆, 円角 美智子, 岡島 悟
1980 年 28 巻 9 号 p.
2602-2608
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
Irradiation of the 1-substituted isoquinoline N-acylimides (3), prepared from isoquinolines (1) by successive N-amination and acylation, brought about a novel photoinduced two-step rearrangement to form the fully unsaturated 1H-1, 3-benzodiazepines (4), which were converted into the indole derivative (10) by treatment with acids via the ring-opened intermediate (8) or into (11) upon irradiation presumably via the tricyclic valence isomer (14).
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柴沼 忠夫, 岩波 勝, 藤本 正治, 竹中 登一, 村上 増雄
1980 年 28 巻 9 号 p.
2609-2613
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
Eight metabolites (M-1-M-6, M-8, M-9) of 2-(N-benzyl-N-methylamino)ethyl methyl 2, 6-dimethyl-4-(m-nitrophenyl)-1, 4-dihydropyridine-3, 5-dicarboxylate hydrochloride (YC-93) were synthesized and the structures of the metabolites were established by comparison with the synthetic compounds.
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高柳 弘明, 小倉 治夫, 早津 彦哉
1980 年 28 巻 9 号 p.
2614-2617
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
The crystal and molecular of N
4-aminocytosine was determined by X-ray diffraction. This compound belongs to the monoclinic space group P2
1/a with four molecules in a unit cell of α=7.950 (2) Å ; b=11.156 (2) Å ; c=6.054 (3) Å ; β=94.59 (2)° ; V=535.2 (3) Å
3. The final R value was 0.072 including hydrogen atoms. The present study established that this compound takes the C (4)-amino form rather than the imino form, and is consistent with the report (D. M. Brown, M. J. E. Hewlins and P. Schell, J. Chem. Soc. (C), 1968, 1925 that 1-methyl-N
4-aminocytosine takes the amino form in solution.
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日野 克彦, 古川 清, 永井 保嵩, 宇野 準
1980 年 28 巻 9 号 p.
2618-2622
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
A series of 2-amino-4-phenylquinolines was synthesized and the effects of these compounds on the central nervous system were evaluated pharmacologically in mice. Among these compounds, many 2-(substituted piperazinyl) derivatives exhibited a potent antagonism to hypothermia and catalepsy induced by reserpine, as well as some inhibitory effect on locomotor activity. Some compounds were found to possess activity to inhibit tremorine-induced tremor.
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大和 正利, 堀内 次郎, 竹内 靖雄
1980 年 28 巻 9 号 p.
2623-2628
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
Acylation of spiro[piperidine-4, 2'-(1', 2', 3', 4'-tetrahydroquinazolin)]-4'-ones (1d, 4, 6, and 7) was attempted. In all cases, the resulting products were not the corresponding acyl derivatives but two types of products (2 or 3 and 5). Heating 1d, the derivative having hydrogen atoms on the N
(1) and N
(3)-positions of spiro[piperidine-4, 2'-(1', 2', 3', 4'-tetrahydroquinazolin)]-4'-ones with acetic anhydride or benzoic anhydride gave 1-(1-benzyl-1, 2, 5, 6-tetrahydro-4-pyridyl)-2-methyl-1, 4-dihydroquinazolin-4-one (2) or 1-(1-benzyl-1, 2, 5, 6-tetrahydro-4-pyridyl)-2-methyl-1, 4-dihydroquinazolin-4-one (3), respectively. On the other hand, heating 4, the N
(1)-substituted derivative of 1d, with acetic anhydride gave 2-benzyl-5-methyl-1, 2, 3, 4, 5, 10-hexahydro-benzo[b]-1, 6-naphthyridin-10-one (5). The N
(3)-substituted derivatives (6 and 7) of 1d did not react with acetic anhydride.
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岩波 勝, 前田 哲哉, 藤本 正治, 長野 嘉信, 長野 憲昭, 山崎 敦城, 柴沼 忠夫, 玉沢 一晴, 矢野 邦一郎
1980 年 28 巻 9 号 p.
2629-2636
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
A novel intramolecular rearrangement of isothiazolethioacetamides into 1, 3-dithietanecarboxamides is described, together with the synthesis of a new cephamycin derivative (YM-09330) having a 1, 3-dithietane structure at the 7β-position. This compound showed strong antibacterial activity, especially against gram-negative organisms.
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竹内 洋文, 三輪 嘉尚, 岡田 寿太郎
1980 年 28 巻 9 号 p.
2637-2641
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
Vapor-phase synthesis of benzyl cyanide from 2-phenylethanol and ammonia was studied over Ni-Cu-SiO
2 catalyst in the presence of hydrogen. Experiments were carried out in a flow reactor system under atmospheric pressure at 300°. The main product was benzyl cyanide, and toluene and phenethylamine were also produced. The Ni-Cu-SiO
2 catalyst (Ni/Cu=3/1) gave the best selectivity for benzyl cyanide, 80%. The deactivation of this catalyst was negligible. By kinetic analysis, the rate of loss of 2-phenylethanol was found to show a first order dependency on the partial pressure of 2-phenylethanol, and was not affected by the partial pressures of ammonia and hydrogen. The experimental data were well interpreted by a model in which phenethylimine was produced as an intermediate and was then dehydrogenated to benzyl cyanide.
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田上 昇一郎
1980 年 28 巻 9 号 p.
2642-2646
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
Meprobamate decomposes into NH
4Cl, CO
2, and a diol compound on heating in 20% HCl, and the NH
3 evolved at pH above 11 can be determined using the NH
3 selective electrode without separation from the decomposition solution. A linear calibration plot was obtained within the concentration range of 1×10
-5-1×10
-2M meprobamate. Volatile amines and the Hg ion, which forms a metal complex with NH
3, are known to interfere with the electrode measurements.
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鵜飼 茂夫, 原 千尋, 木方 正, 広瀬 一雄
1980 年 28 巻 9 号 p.
2647-2652
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
A new type of mannan (T-2-HN) has been isolated as a neutral homoglycan from the aqueous 70% ethanol extract of the fruit bodies of Dictyophora indusiata FISCH., which grows in China. T-2-HN was homogeneous as judged by gel filtration (Sepharose 2B) and Tiselius-type electrophoresis. It was composed of D-mannose and a trace of glucose in a molar ratio of 100 : 1, and contained O-acetyl groups in the proportion of about one acetyl group per two sugar residues. Its highly positive specific rotation, [α]
20D+116°(c=0.1, H
2O), and the presence of an absorption band at 820 cm
-1 (type 2a) in the infrared spectrum suggested that most of the glycosidic linkages in this mannan are of α-D configuration. Structural analysis indicated that T-2-HN has a linear chain composed largely of α-1→3 linked D-mannosyl residues, but the linear chain also contains traces of 1→6 linked D-mannopyranosyl (and/or glucosyl) residues. In addition, trace amounts of branching points are present at position 2 or 4 on each of the 1→3 linked D-mannose residues.
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山上 知佐子, 杉浦 真喜子, 田村 嘉鶴, 高尾 楢雄
1980 年 28 巻 9 号 p.
2653-2657
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
The behavior of several N-substituted-4-piperidones in methanol has been studied by
13C nuclear magnetic resonance (NMR) spectroscopy. All the piperidones studied were found to be equilibrium with their hemiacetals in methanolic solutions. The features of N-acyl derivatives were different from those of N-alkyl derivatives and the differences could be accounted for by electronic factors. The chemical shifts of the acetals were also determined and a procedure for distinguishing between hemiacetal and acetal is proposed.
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京坂 重久, 山城 早苗, 田中 光也
1980 年 28 巻 9 号 p.
2658-2664
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
Porcine kidney β-acetylhexosaminidase A was purified to electrophoretic homogeneity by procedures involving ammonium sulfate precipitation, gel filtration and column chromatography on diethylaminoethyl cellulose, octyl Sepharose CL-4B and ε-aminohexanoyl β-acetylglucosaminylamine-Sepharose 4B. Analysis by sodium dodecyl sulfate-gel electrophoresis suggested that the enzyme consists of three subunits with molecular weights of 61000, 31000 and 9000. The molecular weight of the intact enzyme as determined by gel filtration was 129000 at pH 8.0 and 302000 at pH 5.0. Kinetic analysis with mixed substrates as well as inhibition studies with various substrate analogs, indicated that the enzyme hydrolyzes both β-N-acetylglucosaminide and β-N-acetylgalactosaminide at the same active site. Among hexoses tested for inhibitory effect, only mannose was an effective competitive inhibitor. A comparison of mannosides with N-acetylglucosaminides with respect to binding ability to the enzyme in terms of K
1 or K
m values implied the presence of a site for mannose other than the active site. On the other hand, kinetic studies with mixed inhibitors indicated that mannose competes with N-acetylgalactosamine, N-acetylglucosamine and acetamide.
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松田 芳久, 糸岡 俊子, 三橋 佳子
1980 年 28 巻 9 号 p.
2665-2671
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
The dependence of the photostability of indomethacin on the capsule shell thickness and on the concentration of titanium dioxide used as an opacificient was investigated using gelatin films prepared by casting as models of hard gelatin capsules. The film thickness and concentration of opacificient were varied in the ranges of 50-150μm and 0-1.5% of the amount of dried films, respectively. Films and indomethacin tablets were exposed to a 400 W mercury vapor lamp for 120 min, then coloration of the enclosed indomethacin was measured by tristimulus colorimetry, and evaluated as Hunter's color difference. The chemical stability of the drug was determined by following the ultraviolet spectrophotometric change of a solid sample. There was a good linear relationship between color difference values and the square root of exposure time at all concentrations and thicknesses. The coloration rate constants calculated from the slopes of these lines were affected by both parameters, and decreased significantly as the film thickness was increased at every concentration of opacificient. However, the effect of concentration seemed to disappear above 1% addition. The coloration rate was directly dependent on the average transmittance of films over the wavelength range relating to the photostability of indomethacin. Degradation of indomethacin followed apparently sequential first-order kinetics. Apparent conversions after 120-min exposure as determined from the UV spectra were also affected by both parameters and were below 3% at thicknesses above 80μm at every opacificient concentration tested ; this represents excellent protection of indomethacin.
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松島 美一, 菅田 節朗, 西園寺 裕子, 筒井 稔
1980 年 28 巻 9 号 p.
2672-2675
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
meso-Tetra[5-(8-hydroxyquinolyl)]porphine was synthesized by the Rothemund method as a model of porphyrin with metal chelating groups in the peripheral region. The presence of three kinds of copper (II) complexes was demonstrated ; free base porphyrin with metal chelated 8-quinolinol groups and metalloporphyrin with metal chelated and unchelated 8-quinolinol groups. In dimethylformamide solution, reaction of the compound with excess copper (II) perchlorate occurred in two steps ; rapid metal chelation of the 8-quinolinol moiety and subsequent slow Cu (II) incorporation into the porphine moiety. Reaction with excess aluminum (III) nitrate under similar conditions gave free base porphyrin with Al (III) chelated 8-quinolinol groups.
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土屋 隆, 栗田 城治, 高山 和子
1980 年 28 巻 9 号 p.
2676-2681
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
Photolyses of various diazine N-ethoxycarbonylimides (3, 9, and 19), prepared from the corresponding diazines (1, 8, and 17), resulted in the formation of the pyrazole derivatives (4 and 10) from pyrazine and pyrimidine N-imides, and of the pyrrole derivatives (20) from pyridazine N-imides. These photolyses may proceed by rearrangement to diaziridine intermediates, followed by ring expansion to the corresponding 1, 2, 5-, 1, 2, 4-, or 1, 2, 3-triazepines (6, 12, or 22), which then undergo isomerization to the triaza[3.2.0]bicycloheptadienes (7, 13, and 23), followed by elimination to give the products (4, 10, and 20, respectively).
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野原 稔弘, 徳淵 信能, 黒岩 美保子, 西岡 五夫
1980 年 28 巻 9 号 p.
2682-2686
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
Compounds 7-13 were isolated from the water extractive of Cinnamomi Cortex (the dried bark of Cinnamomum cassia BLUME, "Toko Keihi"in Japanese, Lauraceae), which shows anti-complement activity. Among them, the compounds 7 and 8 were characterized by chemical and spectral means and named cinncassiol B and cinncassiol B 19-O-β-D-glucopyranoside, respectively.
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三野 芳紀, 太田 長世, 坂尾 聡, 下村 滋
1980 年 28 巻 9 号 p.
2687-2691
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
Flameless atomic absorption spectrometry combined with solvent extraction was developed for the determination of germanium in medicinal plants. A wet oxidation procedure using only nitric acid was suitable for ashing plant samples. Carbon tetrachloride and water were used as solvents for extraction and back-extraction. Measurements were carried out after preparing sample solutions in 0.5 M sodium hydroxide in order to enhance the sensitivity. This high sensitive method (detection limit, 1 ppb) was applied to the determination of germanium in some medicinal plants. The analytical results obtained indicate that medicinal plants contain small amounts of germanium ; it appeared that there was no connection between the pharmacological effects of medicinal plants and their germanium contents.
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川崎 紘一, 川崎 知恵, 津田 裕子, 前田 光子, 岡田 芳男, 山地 建二, 高木 哲, 谷沢 修
1980 年 28 巻 9 号 p.
2692-2698
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
A hexadecapeptide, H-Arg-Leu-Pro-Gly-Pro-Asn-Thr-Pro-Ile-Leu-Pro-Gln-Ser-Leu-Pro-OH, corresponding to the C-terminal sequence 132-147 of hCG-β proposed by Carlsen et al., was synthesized stepwise by fragment condensation, assembling five fragments [Z-Arg(NO
2)-Leu-Pro-NHNHBoc, Z-Gly-Pro-Pro-NHNHBoc, Z-Asn-Thr-Pro-NHNHBoc, Z-Ile-Leu-Pro-NHNHBoc, and Z-Gln-Ser-Leu-Pro-OBu
t].
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川崎 紘一, 川崎 知恵, 津田 裕子, 柳生 正見, 岡田 芳男, 山地 建二, 高木 哲, 谷沢 修
1980 年 28 巻 9 号 p.
2699-2706
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
A dotriacontapeptide, H-Gln-Asp-Ser-Ser-Ser-Lys-Ala-Pro-Pro-Pro-Ser-Leu-Pro-Ser-Pro-Ser-Arg-Leu-Pro-Gly-Pro-Pro-Asn-Thr-Pro-Ile-Leu-Pro-Gln-Ser-Leu-Pro-OH, corresponding to the C-terminal sequence 116-147 of hCG-β proposed by Carlsen et al. was synthesized by stepwise fragment condensation, linking five fragments [Z-Gln-Asp(OBzl)-OH, Z-Ser(Bzl)-Ser-Ser-Lys(Boc)-NHNH
2, Z-Ala-Pro-Pro-Pro-NHNHBoc, Z-Ser(Bzl)-Leu-Pro-NHNHBoc, and Z-Ser(Bzl)-Pro-Ser-NHNH
2] to the hexadecapeptide reported in the preceding paper.
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岡田 芳男, 井口 伸, 三村 昌司, 川崎 紘一, 山地 建二, 高木 哲, 谷沢 修
1980 年 28 巻 9 号 p.
2707-2713
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
The hexadecapeptide corresponding to sequence 130-145 of the β-subunit of human chorionic gonadotropin (hCG) according to the amino acid sequence proposed by Morgan et al. was synthesized by successive azide condensation of 4 peptide fragments, followed by TFA treatment and catalytic hydrogenation. This peptide was conjugated with bovine serum albumin (BSA). Antiserum produced against this conjugate did not bind with
125I-hCG.
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岡田 芳男, 井口 伸, 柳生 正見, 川崎 紘一, 山地 建二, 高木 哲, 谷沢 修
1980 年 28 巻 9 号 p.
2714-2719
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
The triacontapeptide corresponding to sequence 116-145 of the β-subunit of human chorionic gonadotropin (hCG) according to the amino acid sequence elucidated by Morgan et al. was synthesized by successive azide condensation of 5 peptide fragments, followed by TFA treatment and catalytic hydrogenation. This peptide was conjugated with bovine serum albumin (BSA). A 1% binding of
125I-hCG was observed with the antiserum produced against the conjugate obtained above at a 1 : 500 dilution.
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真野 光彦, 瀬尾 卓司, 今井 欣一
1980 年 28 巻 9 号 p.
2720-2733
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
2(1H)-Pyrazinone 4-oxide (emimycin) and its 1- and 6-substituted derivatives were synthesized by the reaction of a variety of 2-(hydroxyamino)acetamides with glyoxals.
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真野 光彦, 瀬尾 卓司, 服部 俊則, 金児 龍彦, 今井 欣一
1980 年 28 巻 9 号 p.
2734-2747
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
A series of 1-, 3-, 5- and 6-substituted 2(1H)-pyrazinone 4-oxides were synthesized and tested for anticoccidial activity. Of the compounds tested, 1-(β-D-ribofuranosyl)-(22), 1-(2, 3, 5-tri-O-benzoyl-β-D-ribofuranosyl)-(21) and 1-(2, 3, 5-tri-O-acetyl-β-D-ribofuranosyl)-2(1H)-pyrazinone 4-oxides (24) showed high activity.
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土田 清美, 池田 一芳, 水野 義久
1980 年 28 巻 9 号 p.
2748-2752
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
3-(2-Amino-2-carboxyethyl)uracil (racemic isowillardiine) was synthesized by the use of a four-component (aldehyde, amine, isocyanide, and carboxylic acid) condensation as the key reaction. Thus, 1-(2-picolyl 1-oxide)-3-(formylmethyl) uracil was allowed to react with 2-picolylamine 1-oxide and cyclohexyl isocyanide or 2-picolyl isocyanide 1-oxide in the presence of acetic acid in methanol to afford the corresponding condensation product, which after deblocking, gave (±)-isowillardiine in fair yield.
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岡部 光, 宮原 由美, 山内 辰郎, 宮原 由美, 川崎 敏男
1980 年 28 巻 9 号 p.
2753-2762
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
Two triterpene glycosides, momordicosides A and B, were isolated from the seeds of Momordica charantia L. (Cucurbitaceae). Their structures were determined on the basis of spectral and chemical evidence and by X-ray analysis as the 3-O-β-gentiobioside and 3-O-β-D-xylopyranosyl (1→4)-[β-D-glucopyranosyl(1→6)]-β-D-glucopyranoside, respectively, of cucurbit-5-ene-3β, 22(S), 23(R), 24(R), 25-pentaol.
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江口 征夫, 杉本 昭子, 石川 正幸
1980 年 28 巻 9 号 p.
2763-2769
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
4-Hydroxymethyl-1(2H)-phthalazinone derivatives were synthesized and assayed for their inhibitory effects on platelet aggregation and edematous arterial reaction. Among the tested compounds, 7-ethoxycarbonyl-4-hydroxymethyl-1(2H)-phthalazinone showed the highest potency in these pharmacological tests. The structure-activity relationship of phthalazinone derivatives and related compounds is discussed.
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石川 正幸, 江口 征夫, 杉本 昭子
1980 年 28 巻 9 号 p.
2770-2778
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
To enhance the biostability of the ester linkage of 7-ethoxycarbonyl-4-hydroxymethyl-1(2H)-phthalazinone, which has potent biological activities, the corresponding tert-butyl ester (1e) and 7-ethoxycarbonyl-4-hydroxymethyl-6, 8-dimethyl-1(2H)-phthalazinone (EG 626) (6) were prepared. The synthesis and inhibitory effects on platelet aggregation and edematous arterial reaction of these and other closely related compounds were investigated. EG 626 appears to be a potentially effective antithrombotic and antiatherosclerotic agent.
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稲山 誠一, 徳永 友喜子, 細谷 栄吉, 中館 映夫, 丹羽口 徹吉, 青木 喜美子, 斎藤 章二
1980 年 28 巻 9 号 p.
2779-2782
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
N-Carboxymethylmethamphetamine, a derivative of methamphetamine, was prepared through a new synthetic pathway from ephedrine. Specific antiserum was obtained by immunization of rabbits with the conjugate of N-carboxymethylmethamphetamine with bovine serum albumin. A radioimmunoassay procedure was established using this antibody (specific for methamphetamine) and a
125I-methamphetamine derivative. A high degree of specificity of the antibody was confirmed by testing for cross-reaction with several methamphetamine analogs, and the sensitivity was found to be 1 ng/tube. The present micro method using radioimmunoassay is highly sensitive, rapid, simple and may be useful as a micro-scale primary screening test for methamphetamine excreted in human urine, for forensic and medical purposes.
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山岸 輝里, 越中 栄一, 小川 信男, 見谷 一也, 西川 公康, 加藤 日出男, 花岡 美代次
1980 年 28 巻 9 号 p.
2783-2795
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
As part of a search for new antispasmodics, we have synthesized N-alkyl 6- and 7-diarylmethyleneindolizidinium bromides (1-8), which might be expected to exhibit potent anticholinergic activities due to the rigid piperidine ring structure, by analogy with N-alkyl 2- and 3-diarylmethylenequinolizidinium bromides (I). Treatment of ethoxycarbonylindolizidines (13 and 22) with phenyllithium or 2-thienylmagnesium bromide, followed by dehydration, afforded diarylmethyleneindolizidines (25, 26, 29 and 30). Quaternization of the 6-substituted derivatives (25 and 26) with methyl bromide afforded two isomeric methobromides, the trans- (1a and 2a) and the cis-methobromides (1b and 2b), and the 7-substituted derivatives (29 and 30) also afforded the corresponding trans- (5a and 6a) and cis-methobromides (5b and 6b). The stereochemistries of these methobromides were confirmed by the chemical shifts of the N
+-methyl signals in the
1H- and
13C-NMR spectra. The stereochemistries of 6- and 7-diarylhydroxymethylindolizidines (23, 24, 27 and 28) were also determined from their IR and
13C-NMR spectra.
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相楽 和彦, 柿沢 定男, 粕谷 浩次, 岬 哲夫, 吉沢 弘
1980 年 28 巻 9 号 p.
2796-2799
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
A new simple gas chromatographic method for the simultaneous determination of capsaicin, dihydrocapsaicin and nordihydrocapsaicin in capsicum fruit was developed. The three components extracted from capsicum fruit could be completely separated on a 3% Apiezon grease L column. Quantitative analysis could be achieved by the peak area ratio method using methyl arachidate as an internal standard. The results obtained by this method were in good accord with those obtained by mass chromatography.
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橋本 敏弘, 加藤 義成, 長岡 由岐代, 太田 知三, 佐藤 大助
1980 年 28 巻 9 号 p.
2799-2803
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
Solvent effects on the dimerization of 16, 17-dehydrodigitoxigenin 3-acetate (I) were investigated. Heating of I in less polar solvents, such as toluene, xylene, dioxane or tetrahydrofuran, gave the dimer III as the main product, in similar yields. The reaction in slightly basic media, such as toluene containing sodium acetate or dimethylformamide, afforded an isomeric dimer IV preferentially. The structure of IV was established on the basis of its spectral data and anhydration reaction in contrast to those of III. A mechanism is proposed for the formation of IV from I.
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杉浦 衛, 及川 勉
1980 年 28 巻 9 号 p.
2803-2806
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
Lipoprotein lipase (glycerol ester hydrolase ; EC 3.1.1.3) from Pseudomonas fluorescens was oxidized with N-bromosuccinimide at 37°. One mol of tryptophan residue per mol of enzyme was oxidized, but the enzymatic activity was unaffected. The enzyme was inactivated by photooxidation in the presence of methylene blue, and the inactivation was pH-dependent. In addition, the decrease in the enzymatic activity was accompanied by the loss of a histidine residue. It appears that the histidine residue in involved in the catalytic activity of the enzyme.
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高田 寛治, 山本 緑, 中江 裕子, 浅田 昌三
1980 年 28 巻 9 号 p.
2806-2808
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
The effects of a sulfonic acid dye and a surfactant on the pulmonary absorption of fluorescein isothiocyanate-labelled dextran (FITC-dextran), a model macromolecular compound (MW=150000) which is not absorbed after pulmonary administration, were studied. Bromphenol blue, a sulfonic acid dye, did not show an enhancing effect. However, sodium glycocholate (SGC) considerably enhanced the pulmonary absorption of FITC-dextran. Therefore, SGC may be a useful additive to increase the systemic availability of macromolecular compounds administered as aerosol dosage forms.
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柴沼 忠夫, 岩波 勝, 奥田 幸平, 竹中 登一, 村上 増雄
1980 年 28 巻 9 号 p.
2809-2812
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
(+)- and (-)-2-(N-benzyl-N-methylamino)ethyl methyl 2, 6-dimethyl-4-(m-nitrophenyl)-1, 4-dihydropyridine-3, 5-dicarboxylate (6) (nicardipine) were synthesized from (-)- and (+)- 1-ethoxymethyl-5-methoxycarbonyl-2, 6-dimethyl-4-(m-nitrophenyl)-1, 4-dihydropyridine-3-carboxylic acid (3), respectively. Resolution of 3 was carried out using cinchonidine and cinchonine as resolving agents. The vertebral vasodilating activity of (+)-YC-93 (the hydrochloride of (+)-(6)) was about 3 times that of (-)-YC-93.
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陳 勝智, 中村 洋, 田村 善蔵
1980 年 28 巻 9 号 p.
2812-2816
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
A simple method for the fluorometric determination of fluorescein and fluorescein monoglucuronide in urine was developed. Free fluorescein was determined by measuring its native fluorescence at 494 nm excitation and 516 nm emission. The conjugate was determined as fluorescein after hydrolysis at 37°for 20 min with β-glucuronidase. This method was applied to investigate the glucuronidation function of Wistar rats with liver injury in comparison with that of normal rats.
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伊藤 めぐみ, 中野 真汎
1980 年 28 巻 9 号 p.
2816-2819
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
The use of ethylcellulose microcapsules possessing a reservoir system to achieve sustained release of sulfamethizole or 5-fluorouracil was examined in vitro. As a first step, the drugs were dispersed in cellulose acetate matrices, then the matrices were microencapsulated by means of coacervation-phase separation of ethylcellulose from diethyl ether solution by nonsolvent addition. The surfaces of microcapsules were rounded, whereas the milled matrices were sharp-edged. In microcapsules of both drugs, longer release half-lives were obtained than with the corresponding matrices.
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板谷 泰助, 小川 和男, 松本 浩郎, 渡辺 朝子
1980 年 28 巻 9 号 p.
2819-2824
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
Heating N, N-diethyl-3, 9-dialkyladeninium halides (Ig-j) in aqueous sodium hydroxide gave 1-alkyl-5-(alkylamino)imidazole-4-carboxamides (IV) together with minor amounts of 1-alkyl-5-(alkylamino)imidazole-4-carbonitriles (III), which were converted into IV on further heating. N, N-Dimethyl-3, 9-dialkyladeninium halides (Ia-d) underwent hydrolysis more rapidly to provide IV selectively in 90-94% yields.
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前田 忠男, 武仲 宏, 山平 良也, 野口 豪, 野口 哲男
1980 年 28 巻 9 号 p.
2824-2826
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
The usefulness of stomach-emptying-(SE-) controlled rabbits for GI absorption studies of relatively water-soluble drugs was investigated, employing aminopyrine and sulfisoxazole as model drugs. When aminopyrine was administered, similar plasma level-time curves were obtained in both SE-controlled and conventionally fasted rabbits. In the case of sulfisoxazole, the time required to reach the peak plasma level was much longer in conventionally fasted rabbits than in the SE-controlled group. It was concluded that use of conventionally fasted rabbits for GI absorption studies should be limited to work on water-soluble drugs.
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木津 治久, 富森 毅
1980 年 28 巻 9 号 p.
2827-2830
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
Four triterpenoid prosapogenins tentatively named CP
1, CP
3, CP
4 and CP
5 were isolated from the alkaline hydrolysate of the crude saponin obtained from the root of Clematis chinensis OSBECK. On the basis of chemical and physicochemical evidence, they were characterized as follows : CP
1 (I), hederagenin 3-O-α-L-arabinopyranoside ; CP
3 (II), oleanolic acid 3-O-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside ; CP
4 (VI), oleanolic acid 3-O-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside ; CP
5 (VIII), hederagenin 3-O-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside.
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岡林 一蔵, 岩田 典子
1980 年 28 巻 9 号 p.
2831-2835
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
1-Chloroxanthone (2) was obtained by cyclization of 2-chloro-6-phenoxybenzoic acid (10) prepared from 2-nitro-6-phenoxybenzoic acid (8) via 2-amino-6-phenoxybenzoic acid (9). Similarly, 1, 5-dichloroxanthone (14a) and 1, 7-dichloroxanthone (14b) were obtained from 2-(2-chlorophenoxy)-6-nitrobenzoic acid (11a) and 2-(4-chlorophenoxy)-6-nitrobenzoic acid (11b), respectively. Furthermore, 2, 6-dichloroxanthone (19) was prepared by cyclization of 4-chloro-2-(4-chlorophenoxy)benzoic acid (18). Dichloroxanthone B, obtained by cyclization of 5-chloro-2-(3-chlorophenoxy)benzoic acid (16) and reported by Nargund et al. as 1, 7-dichloroxanthone, could not be separated into 1, 7-(14b) and 2, 6-dichloroxanthone (19) by recrystallization, column chromatography or thin-layer chromatography, but was proved here to be a mixture of 14b and 19 by gas chromatography.
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峯尾 哲, 小倉 治夫, 中川 国夫
1980 年 28 巻 9 号 p.
2835-2838
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
Oxidation of 6-amino-5-benzylideneamino-1, 3-dimethyluracils (Ia-e) with nickel peroxide (Ni-PO) in dimethylsulfoxide (DMSO) afforded 8-substituted theophyllines (IIa-e) and dimethylsulfone. Ni-PO oxidation of the Schiff base acetate (V) of 5, 6-diamino-1, 3-dimethyluracil with D-glucose did not give a nucleoside analog ; in stead, 1, 3, 7, 9-tetramethyl-2, 4, 6, 8-(1H, 3H, 7H, 9H)pyrimido[5, 4-g]pteridinetetrone (VI) and penta-O-acetylgluconic acid were obtained. The reaction mechanisms of Ni-PO and the Schiff bases (Ia-e, V) are discussed.
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岡本 憲治, 安村 貢一, 島村 真一, 中西 重忠, 沼 正作, 井村 裕夫, 田中 明, 中村 益久, 矢島 治明
1980 年 28 巻 9 号 p.
2839-2842
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
The dodecapeptide corresponding to γ-melanotropin, a newly found amino acid sequence in bovine corticotropin-β-lipotropin precursor protein, was synthesized in a conventional manner. The synthetic peptide exhibited weak melanocyte-stimulating activity, but failed to show any significant steroidogenic and lipolytic activities.
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田中 信寿, 長瀬 幸子, 和知 恭子, 村上 孝夫, 斎木 保久, 陳 秋明
1980 年 28 巻 9 号 p.
2843-2845
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
From the fronds of Dennstaedtia scandens (BLUME) MOORE a new acylglucose was isolated and identified as 1, 4-di-O-p-coumaroyl-β-D-glucose. As further extractives, the following compounds were isolated : p-hydroxybenzoic acid, methyl p-coumarate, pinocembrin-7-O-β-D-glucoside, vitexin and isovitexin.
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田中 昭, 臼井 敏直, 島津 正治
1980 年 28 巻 9 号 p.
2846-2849
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
5-(2-, 3-, 4-Substituted phenoxy)-2-furancarbaldehydes were prepared by the reaction of various phenoxides with 5-nitro-2-furancarbaldehyde via replacement of the nitro group.
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西沢 信, 山岸 喬, 野中 源一郎, 西岡 五夫
1980 年 28 巻 9 号 p.
2850-2852
発行日: 1980/09/25
公開日: 2008/03/31
ジャーナル
フリー
The gallotannins (polygalloylglucoses) were isolated homogeneously from Paeoniae Radix and their structures were elucidated by
13C-nuclear magnetic resonance spectroscopy.
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