YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
99 巻, 5 号
選択された号の論文の19件中1~19を表示しています
  • 濱田 喜樹, 杉浦 道治
    1979 年 99 巻 5 号 p. 445-450
    発行日: 1979/05/25
    公開日: 2008/05/30
    ジャーナル フリー
    Treatment of commercially easily available quinoline, isoquinoline, benzo [f] quinoline, 5-, 6-, or 8-nitroquinoline, 2-, 4-, 6-, 7-, or 8-methylquinoline, and 6-methoxyquinoline with cyanogen bromide and sodium hydrogen carbonate in methanol affords the corresponding 1-cyano-2-methoxy-1, 2-dihydroquinolines and 2-cyano-1-methoxy-1, 2-dihydro-isoquinolines in a high yield. The yield of the objective compounds from this reaction is about twice that of the von Braun reaction not using sodium hydrogen carbonate. By the use of this reaction, synthesis of 3-bromoquinaldine, which had been difficult to synthesize heretofore, was established, and synthetic method for 3-bromo-4-(or 6-, 7-, 8-)-methylquinolines was also improved.
  • 竹内 烈, 小澤 勇夫, 重村 堅太郎, 濱田 喜樹, 伊藤 富由, 大山 昭夫
    1979 年 99 巻 5 号 p. 451-457
    発行日: 1979/05/25
    公開日: 2008/05/30
    ジャーナル フリー
    Reaction of quinoline 1-oxide (I) with o-, m-, or p-methoxyphenylmagnesium bromide in tetrahydrofuran afforded the corresponding 2-(o- or p-methoxyphenyl) quinoline 1-oxides (II and V) and their deoxygenated compounds, 2-(o-, m-, or p-methoxyphenyl) quinolines (III, IV, and VI). II, III, V, and VI were hydrolyzed with hydrobromic acid in acetic acid to form their hydroxy compounds (VII to X). Reaction of 1, 8-naphtyridine 1-oxide (XI) with o-methoxyphenyllithium in ether afforded 2-(o-methoxyphenyl)-1, 8-naphthyridine (XII) which was hydrolyzed to the hydroxy compound (XIII). Optimal conditions for the reaction of pyridine 1-oxide (XIV) and benzyne were examined and the best condition was applied to XI. Reaction by method b afforded 2- and 3-(o-hydroxyphenyl)-1, 8-naphthyridines (XIII' and XIX). Antibacterial tests of the synthesized compounds and 2-phenyl-1, x-naphthyridine x=5, 6, 7, 8) (XX to XXIII) showed that III had a wide antibacterial spectrum and that VIII had a stronger antibacterial activity than other compounds against Pseudomonas aeruginosa.
  • 絵柳 玲子, 吉田 和夫, 山本 郁男
    1979 年 99 巻 5 号 p. 458-465
    発行日: 1979/05/25
    公開日: 2008/05/30
    ジャーナル フリー
    The antigenicity of some metabolites of sulfanilamide and their related compounds was studied by three kinds of experiments, 1) protein binding, 2) skin reaction in guinea pigs and 3) antibody formation to 4-hydroxylaminobenzenesulfonamide (4-HABSA). 1) The strong binding of 4-HABSA to bovine serum albumin (BSA) and rat serum protein was found by extensive equilibrium dialysis and gel filtration on a Sephadex G-25 column. 2) In addition, in both groups of guinea pigs sensitized with SA or 4-HABSA, positive skin reaction was observed 24 hr after elicitation by injections of 4-HABSA, 4-nitro-sobenzenesulfonamide (4-NSBSA), 4, 4'-azoxybenzenedisulfonamide (4, 4'-AZOBDSA), 4, 4'-azobenzenedisulfonamide (4, 4'-AZBDSA) and 4, 4'-hydrazobenzenedisulfonamide (4, 4'-HAZBDSA). 3) We also attempted to detect antibodies to 4-HABSA in the antisera of rabbits sensitized with 4-HABSA alone or 4-HABSA-BSA conjugate using passive hemagglutination tests. It is thought that 4-HABSA conjugated with tissue proteins acts as antigen, although the production of antibody to 4-HABSA hapten is low.
  • 荒木 健伍, 橘 真郎, 加藤 義則, 田島 鉄弥
    1979 年 99 巻 5 号 p. 466-470
    発行日: 1979/05/25
    公開日: 2008/05/30
    ジャーナル フリー
    The effects of xenopsin, a frog skin peptide, on some isolated tissues, rat blood glucose level and vascular permeability were investigated and compared with neurotensin, a hypothalamic peptide. They had a contractile activity on rat stomach strips and guinea pig ileum, and neurotensin is ca. 2 and 4 times more active in the respective tissue than xenopsin. Neurotensin had a positive inotropic action on isolated guinea pig auricle and was 6 times more active than xenopsin and the action of both peptides could not be blocked by propranolol, phentramine mesylate and diphenhydramine. Xenopsin relaxed the rat duodenum with the activity almost equal to that of neurotensin and these response patterns were different from those induced by bradykinin. In hyperglycemic activity on anesthetized rats, neurotensin was several times more active than xenopsin. Xenopsin had a strong ability to increase vascular permeability and its activity was 2 and 20 times more active than neurotensin and bradykinin, respectively. These data indicate that xenopsin has a similar biologically active pattern as neurotensin and generally neurotensin is more active than xenopsin except for vascular permeability.
  • 濱田 喜樹, 杉浦 道治
    1979 年 99 巻 5 号 p. 471-475
    発行日: 1979/05/25
    公開日: 2008/05/30
    ジャーナル フリー
    1-Cyano-2-methoxy-1, 2-dihydroquinolines (I) were dissolved in chloroform or bromo-form, 50% sodium hydroxide solution was added in the presence of a small quantity of interphase transition catalyst, and the mixture was stirred at room temperature, by which the corresponding 3-cyano-1, 1-dichloro (or dibromo)-2-methoxy-1a, 2, 3, 7b-tetrahydro-1H-cyclopropa [c] quinoline derivatives (II) were obtained. I can be obtained easily in one step from the commercial quinoline derivative so that this reaction is a useful two-step synthesis of cyclopropa [c] quinoline derivatives (II) from commercial quinoline derivatives.
  • 上釜 兼人, 平山 文俊, 高杉 紀雄
    1979 年 99 巻 5 号 p. 476-482
    発行日: 1979/05/25
    公開日: 2008/05/30
    ジャーナル フリー
    Interactions of antibacterial 6-ethyl-2, 3, 6, 9-tetrahydro-3-methyl-2, 9-dioxothiazolo-[5, 4-f] quinoline-8-carboxylic acid (tioxacin) with aliphatic amines such as ethylenediamine, n-propylamine, ethanolamine, piperazine, piperidine, and morphorine were studied in water and in solid state. Soluble complex formations between tioxacin and the amines were ascertained by the solubility method, powder X-ray diffractometry, thermal analyses, and IR spectroscopy. Increase in aqueous solubility of tioxacin was found to be proportional to the basicity of the amine, which was reflected in the magnitude of the complex stability constant. The dissolution rate of the complex was significantly higher than that of thioxacin itself in water. Absorption studies in dogs suggested that the amine complex may have a great utility as a rapid dissolving form of tioxacin in oral administration.
  • 門矢 静夫, 長崎 泉吉
    1979 年 99 巻 5 号 p. 483-492
    発行日: 1979/05/25
    公開日: 2008/05/30
    ジャーナル フリー
    Antimicrobial activities of 98 thiazoloquinolinecarboxylic acids were determined in vitro. Activities were classified into four groups, +++, ++, +, -, based on the average bacteriostatic index calculated by the equation, log2 [100/MIC (μg/ml)]. In the 2, 6-disubstituted derivatives, 2-alkoxy compounds were active only against Gram-positive bacteria, while 2-HO, MeO2S and NC derivatives were active only against Gram-negative bacteria. 2-Amino and 2-carbamoyl compounds had no activities. In the 3, 6-dialkyl-2-oxo derivatives, the most effective alkyl substituent was Me or Et group. Replacement of 2-oxo group by thioxo, imino or hydrazino group resulted in lowering of the activities. The maximum activity of 3-N-alkyl compounds existed in the Me group against both Gram-positive and -negative bacteria, while the corresponding 2-O-alkyl derivatives became stronger against Gram-positive bacteria, but weaker against Gram-negative bacteria with the increase in the length of methylene chain. 6-Ethyl-2, 3, 6, 9-tetrahydro-3-methyl-2, 9-dioxothiazolo [5, 4-f] quinoline-8-carboxylic acid was found to have the highest activities against Gram-positive and -negative bacteria including Escherichia coli resistant to nalidixic acid and Pseudomonas aeruginosa.
  • 濱田 喜樹, 杉浦 道治
    1979 年 99 巻 5 号 p. 493-499
    発行日: 1979/05/25
    公開日: 2008/05/30
    ジャーナル フリー
    Application of dichlorocarbene to 1-alkylquinolinium halide (1), obtained easily from commercial quinoline derivatives and alkyl halide, in chloroform afforded 1, 1-dichloro-3-methyl (or ethyl)-1a, 2, 3, 7b-tetrahydro-2-(trichloromethyl)-1H-cyclopropa [c] quinoline derivatives (6) in a high yield, by the introduction of carbon chains into 2, 3, and 4 positions adjoining the ring nitrogen atom. Synthesis of 6 had hitherto been difficult, and the present method offers a novel two-step synthesis of 6 from commercial quinoline derivatives. Treatment of 6 with lithium aluminum hydride in tetrahydrofuran produced 1, 1-dichloro-2-(dichloromethyl)-3-methyl (or ethyl)-1a, 2, 3, 7b-tetrahydro-1H-cyclopropa [c]-quinoline and its treatment with conc. hydrochloric acid in methanol gave 1, 1-dichloro-2-(methoxycarbonyl)-3-methyl (or ethyl)-1a, 2, 3, 7b-tetrahydro-1H-cyclopropa [c] quinoline. However, the compound (1c) having a benzyl group in 1-position failed to give a dichlorocarbene adduct, and the compounds (1k, m) having a nitro group in 5- or 6-position did form dichlorocarbene adducts.
  • 井上 謙一郎, 塩原 義則, 陳 成章, 柵山 祥代, 井上 博之
    1979 年 99 巻 5 号 p. 500-504
    発行日: 1979/05/25
    公開日: 2008/05/30
    ジャーナル フリー
    Two new compounds, 2-(4-hydroxyphenyl) ethyl triacontanoate (10) and 1-octacosanoyl glyceride (11), along with two known compounds, tetracosanoic acid (12) and n-hexacosyl ferulate (13), were isolated from the wood of Catalpa ovata G. DON and their structures were elucidated on the basis of spectral data and chemical degradations. Furthermore, catalponone (8), a key biosynthetic intermediate of prenylnaphthoquinone congeners of the plant, and deoxylapachol (9) were isolated for the first time from the same wood.
  • 奥田 拓男, 毛利 和子, 石野 雅子
    1979 年 99 巻 5 号 p. 505-509
    発行日: 1979/05/25
    公開日: 2008/05/30
    ジャーナル フリー
    Dissolution followed by hydrolysis of geraniin during decoction of chopped dried herb of Geranium thunbergii was determined by high-performance liquid chromatography on a column of hydrocarbon polymer. The effects of using vessels of different materials for decoction, on dissolution and hydrolysis of geraniin were also determined. We found that upon slow warming of water, the amount of geraniin in the decoction reaches the maximum in a short time after the water starts to boil, and also that the amount of geraniin then decreases fairly fast. The amount of corilagin which is one of the products of hydrolysis of geraniin, increases at the same time, and continues to increase for some time after most of geraniin disappears. When decoction was carried out in beakers of approximately the same volume and of different materials, no marked difference in the results was noted. However, appreciable differences were observed between an aluminum kettle and an earthen vessel of approximately the same volume and of considerably different weight. Although the traditional way of decoction of crude drugs indicates that use of metalic vessels should be avoided, our results show that the superiority of the earthenware is due to mild warming. The experiments of infusing chopped dried herb of Geranium thunbergii repeatedly in a teapot with hot water showed that this is a good method of extracting geraniin without causing extensive hydrolysis.
  • 吉沢 逸雄, 大内 涼子, 中川 明子, 羽賀 健一, 木村 道也
    1979 年 99 巻 5 号 p. 510-514
    発行日: 1979/05/25
    公開日: 2008/05/30
    ジャーナル フリー
    The metabolic pattern of 2-hydroxy-3-deoxyestradiol in rats was compared with that of estradiol. After intraperitoneal injection of 2-hydroxy-3-deoxyestradiol-6, 7-3H, urinary metabolites were measured by the reverse isotope dilution method. The formation of catechol estrogen was observed in both conjugate fractions, sulfate and glucuronide. Metabolism of this estrogen catechol yielded isomeric 2- and 3-monomethyl ethers in approximately equivalent amounts.
  • 富永 義則, 町田 毅, 奥田 浩人, 松田 芳郎, 小林 五郎
    1979 年 99 巻 5 号 p. 515-520
    発行日: 1979/05/25
    公開日: 2008/05/30
    ジャーナル フリー
    Reaction of 6-aminouracils (Ia, b) with carbon disulfide and dimethyl sulfate in the presence of sodium hydroxide in dimethyl sulfoxide gave methyl 6-aminouracil-5-carbodithioates (IIIa, b). Using an excess of carbon disulfide, the above reaction afforded pyrimido [4, 5-d] [1, 3] thiazine derivative (VII) in good yields. Compound III reacted with amines to give the corresponding 6-amino-5-substituted thiocarbamoyluracils (IXa-j) in good yields. The reaction of IIIa with formamide gave 5-amino-1, 3-dimethylprimido-[4, 5-d] pyrimidine derivatives. (XIa, b, XII) were also obtained by treatment of IXa, c, and IXe with acetic anhydride.
  • 穂積 啓一郎, 北村 桂介, 北出 達也
    1979 年 99 巻 5 号 p. 521-527
    発行日: 1979/05/25
    公開日: 2008/05/30
    ジャーナル フリー
    Highly hydrophobic coating of solid materials by plasma polymerization of tetrafluoroethylene (TFE) in a cylindrical flow-through chamber under a glow discharge condition is described. Growth rate of the coating film depositing on a glass slide was raised with increasing high-frequency input power under plasma condition of relatively low electric field strength, while it was reduced under that of high field strength, presumably because intense fragmentation of the monomer to smaller molecules, useless for polymer formation, took place. Transparency of the coated film having 2000 A thickness was practically 100% throughout the visible light range and gradually decreased with shorter ultraviolet wave length. Effective transparency was also observed in infra-red spectrum with the same film thickness except vc-f vibration at 1400-1000 cm-1. Hydrophobic coating was further applied to ashed biological specimens which have very hydroscopic nature forming droplets in ambient air. Specimens of animal tissues and bacterial spores on glass slides were therefore ashed by low-temperature plasma oxidation and subsequently coated with TFE. The treatment successfully altered the ashed specimens to be nonhygroscopic and at the same time strongly fixed the fine ash structures on the glass slides to make permanent preparations.
  • 高平 正行, 近蔵 嘉和, 草野 源次郎, 野副 重男
    1979 年 99 巻 5 号 p. 528-532
    発行日: 1979/05/25
    公開日: 2008/05/30
    ジャーナル フリー
    Three new spirostane steroids were obtained from a kind of chinese crude drug, "Senshokushichikon."On the basis of physicochemical properties and the results of couples of the reactions, the first compound, which was characterized as the acetate (I), mp 123-124°, C35H50O<11>, was elucidated to be Δ25(27)-pentrogenin acetate. The second compound (II), mp 122-125°, [α] D-93°, C33H52O9 and the third compound (III), mp 130-132°, [α] D-96°, C33H50O9 were shown to be 3-epi-ruscogenin 3-β-D-glucopyranoside and 2-epi-neoruscogenin 3-β-D-glucopyranoside, respectively.
  • 石井 昭男, 久保 和博, 出口 隆志, 田中 正生
    1979 年 99 巻 5 号 p. 533-536
    発行日: 1979/05/25
    公開日: 2008/05/30
    ジャーナル フリー
    The inhibitory effects of ecarazine hydrochloride, hydralazine and some of their metabolites were compared on purified beef heart phosphodiesterase activity and bariumelicited smooth muscle contraction. 1) Ecarazine hydrochloride and hydralazine exhibited weak inhibition on cyclic AMP phosphodiesterase (PDE). The IC50 values (concentration of inhibition resulting in 50 per cent of inhibition) were 2.4×10-3M for ecarazine hydrochloride and >5×10-3M for hydralazine. On the other hand, the metabolites, s-triazolo [3, 4-a] phthalazine-2H-3-one (IC50 8.3×10-5M) and 3-methyl-s-triazolo [3, 4-a] phthalazine (IC50 4.9×10-4M) and the derivatives, 3-propyl-s-triazolo [3, 4-a] phthalazine (IC50 2.5×10-4M) and 3-ethyl-s-triazolo-[3, 4-a] phthalazine (IC50 3.1×10-4M) were potent PDE inhibitors and had the same grade of potency as theophylline. 2) The magnitude of the relaxant effect of s-triazolo [3, 4-a] phthalazine derivatives on Ba2+ contracture was greater than that of ecarazine hydrochloride and hydralazine and this activity correlated with PDE inhibition. The other metabolites, 1-(2H)-phthalazinone, phthalazine and 3-hydroxymethyl-s-triazolo [3, 4-a] phthalazine were the least potent. 3) No antihypertensive activity of these metabolites and derivatives on the blood pressure of spontaneously hypertensive rats was observed.
  • 服部 忠雄, 鷲尾 幸夫, 神谷 則賢, 伊藤 剛正, 井上 正秀
    1979 年 99 巻 5 号 p. 537-539
    発行日: 1979/05/25
    公開日: 2008/05/30
    ジャーナル フリー
    Simultaneous determination of chlorpheniramine maleate (MCP) and dexamethasone (DM) in ointment was established by using high performance liquid chromatography. On a μ-Bondapak C18 column (4 mm i.d.×300 mm) with an eluent of CH3OH : H2O=80 : 20, sufficient separation of MCP, DM and other components in ointment was obtained. MCP and DM in ointment were extracted with CH3OH. A 2μl portion of the extracted solution with naphthalene as internal standard was injected into the column, and the effluent was monitored by ultraviolet detector (λ=254 nm). Coefficients of variation for the determination of MCP and DM in ointment were found to be less than 0.35%. In comparison to other methods (determination of DM with isoniazid dihydrochloride, spectrophotometric determination of MCP by solvent extraction with zincon), the present method was superior in simplicity and accuracy.
  • 富永 義則, 肥田木 省三, 松田 芳郎, 小林 五郎, 酒見 寛郎
    1979 年 99 巻 5 号 p. 540-542
    発行日: 1979/05/25
    公開日: 2008/05/30
    ジャーナル フリー
    Reaction of N-R, 3-R2, 5-R3-pyridinium halide (III) (R=-CH2-COOEt, -CH2CN, -CH2-C6H4-NO2 (p) ; R2=H, Me ; R3=H, Me) with 1-cyano-2, 2-bis (methylthio)-1-phenyl-sulfonylethene (II) in the presence of triethylamine gave the corresponding indolizine derivatives (IV) in a good yield (71-92%) (the yield of III (R=-CH2CN, R2=Me, R3=H) was 38%). Similarly, 3-arylpyrrolo [2, 1-a] isoquinoline (V) was also obtained by the reaction of isoquinolinium N-ylide (IIIg) with II in 85% yield.
  • 奥田 拓男, 毛利 和子, 寺山 香代子, 樋口 恵子, 波多野 力
    1979 年 99 巻 5 号 p. 543-545
    発行日: 1979/05/25
    公開日: 2008/05/30
    ジャーナル フリー
    Geraniin was isolated from herbs of Geranium carolinianum, G. wilfordii, G. wilfordii var. hastatum, G. sibiricum var. glabrius, G. tripartitum, and G. yoshinoi, and also from root bark of Triadica sebifera. The isolations were improved by application of droplet counter-current chromatography. Hyperin was isolated from G. carolinianum, and quercetin from G. yoshinoi.
  • 柴田 丸, 藤井 三映子, 八木 勉
    1979 年 99 巻 5 号 p. 546-550
    発行日: 1979/05/25
    公開日: 2008/05/30
    ジャーナル フリー
    Pharmacological examinations of the crude drug preparation"Kyumeigan"(UK) were carried out in small animals. UK showed a significant decrease in dextran- and carrageenin-induced edema of rat paws. It had no apparent hypothermic, anti-pyretic or analgesic effects in mice and rats. No remarkable effects were observed on stress ulcers of rats, the sleeping time of mice treated with pentobarbital, and castor oil-induced catharsis of mice. Furthermore, UK showed a significant effect of decreasing spontaneous motor activities of mice treated with methamphetamine hydrochloride.
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