YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
85 巻 , 2 号
選択された号の論文の17件中1~17を表示しています
  • 柴崎 寿一郎, 坂本 芳幹, 中村 悦子
    1965 年 85 巻 2 号 p. 87-95
    発行日: 1965/02/25
    公開日: 2010/02/19
    ジャーナル フリー
    Among the thiocarbanilide derivatives, being observed as an effective therapeutic agent for leprosy and tuberculosis, 4, 4′-diethoxythiocarbanilide (EtO-OEt) was administered per os to male rabbits and the metabolites excreted in urine were studied. Ether soluble metabolite was separated by the thin layer chromatography (TLC) and alumina column chromatography into non-reacted EtO-OEt, 4-ethoxy-4′-hydroxythiocarbanilide (EtO-OH), 4, 4′-dihydroxythiocarbanilide (HO-OH), 4, 4′-diethoxycarbanilide (EtO-O-OEt), 4-ethoxy-4′-hydroxycarbanilide (EtO-O-OH) and 4, 4′-dihydroxycarbanilide (HO-O-OH), produced by de-ethylation and desulfurization, as well as the decomposed phenetidine besides a few unknown substances. As to the conjugates, though they were not obtained purely, the Rf values of their crude conjugates were compared with that of synthesized compounds, and the hydrolysis of β-glucuronidase suggested that the presence of O-glucuronides with EtO-OH, EtO-O-OH and HO-OH have been identified. Smith did not observed the desulfurization product in rabbit urine metabolites by the administration of thiocarbanilide (H-H) and its some derivatives. However, the author, by tracing back the metabolism of H-H, identified the desulfurization product 4-hydroxycarbanilide (H-O-OH) by TLC.
  • 井上 博純, 武田 幹男, 檜垣 鴻, 釘田 博至
    1965 年 85 巻 2 号 p. 95-100
    発行日: 1965/02/25
    公開日: 2010/02/19
    ジャーナル フリー
    Reactions of 5-chloro (and trifluoromethyl)-2, 4-disulfamylaniline with both glyoxal and methylglyoxal gave 1, 2, 4, -benzothiadiazine derivatives (II), while reaction of I (X=Cl) with phenylglyoxal produced ketonic dihydrobenzothiadiazine (IV). NaBH4 reduction of II and IV afforded dihydro-1, 2, 4-benzothiadiazine derivatives, III and V. Reaction of I (X=Cl) with some phenylglyoxal derivatives and reduction of the products (VII) and (VII′) were also investigated.
    V showed high diuretic activity of about four times as much as chlorothiazide.
  • 大野 武男, 森 逸男
    1965 年 85 巻 2 号 p. 101-104
    発行日: 1965/02/25
    公開日: 2010/02/19
    ジャーナル フリー
    The condensation of the halogeno substitutes of 2-(2′, 4′-dihydroxybenzoyl) benzoic acid (II), derived from the decomposition of either chloro or bromo-fluorescein (I) in concentrated NaOH solution, and either resorcinol or its halogeno derivatives (III), afforded a new chloro-bromo mixed substituted fluorescein (IV), shown in Table I. When polyphosphoric acid was used as a condensation agent in the reaction, a debromination reaction scarecely took place, and a yield of IV was poor. If the condensation was proceeded at 120-150° in the presence of ZnCl2, a yield of IV was pretty rich, even though debromination reaction was accompanied, and the less number of halogeno substitute (IV) was produced subordinately. A little amount of by-products can be removed by treating them in ethanolic HCl, however, a comparatively larger amount of by-products should be separated through the column chromatography of alumina or magnesol, being followed by the elution with 2-3% NH4OH.
    The production of by-product can be easily identified by the paperchromatography, developed by the solvent mixture of N NaOH-10% C6H5OH-H2O (2:1:7).
  • 入倉 勉, 阿部 泰夫, 玉田 輝巳
    1965 年 85 巻 2 号 p. 104-112
    発行日: 1965/02/25
    公開日: 2010/02/19
    ジャーナル フリー
    A screening test of blood sugar descending action was carried out with 41 kinds of sulfonylurea, semicarbazide, benzothiadiazine and biguanide derivatives. As to a few effective compounds, the efficacy ratio and the tests towards acute toxicity and chronic toxicity were examined and 1-(p-chlorophenylsulfonyl)-3-pyrrolidinourea (No. 7) was found to be effective. The correlation between concentration in serum and blood sugar value was further investigated.
  • 小澤 光, 五味 保男, 大槻 勲夫
    1965 年 85 巻 2 号 p. 112-119
    発行日: 1965/02/25
    公開日: 2010/02/19
    ジャーナル フリー
    Pharmacological properties of several guanethidine derivatives were examined with [2-(hexahydro-1H-azepin-1-yl) ethyl] guanidine sulfate (G-7), [2-(4-methyl-(G-7-CH3), [2-(3, 5-dimethyl-(G-7-(CH3)2), [2-(4-methyl-4-aza-(G-7-N), [2-{4-(p-chlorophenyl)-(G-7-2), -hexahydro-1H-azepin-1-yl} ethyl] guanidine sulfate, [2-(hexahydro-1, 4-thiazepin-1-yl)-(G-7-S), [2-(1-oxo-hexahydro-1, 4-thiazepin-4-yl)-(G-7-SO), [2-(1, 1-dioxo-hexahydro-1, 4-thiazepin-4-yl)-(G-7-SO2), -ethyl] guanidine sulfate and [2-(1, 8, 8-trimethyl-3-aza-bicyclo [3. 2. 1] oct-3-yl) ethyl] guanidine sulfate (G-7-3).
    Among the compounds, G-7-N and G-7-2 showed a hypotensive action on rabbit, rat and cat, but their activities were weaker than that of guanethidine. Unlikely to the case of guanethidine, pressor action of noradrenaline was not potentiated and that of tyramine was not inhibited by G-7-N and G-7-2.
    G-7-2 and G-7-3 possessed a marked muscle relaxation on N. ishiadicus-sartorius preparation of Rana nigromaculata. Their activities were found to be almost the same as that of succinylcholine chloride.
    Analgesic, antitussive, antispasmodic activities were also tested, but their effects were found to be not so strong.
    In general, an introduction of substituents in seven-membered ring resulted in a decrease of hypotensive activities and an increase of toxicities.
  • 長瀬 雄三, 金谷 芳雄, 杉山 明子, 星田 晴彦
    1965 年 85 巻 2 号 p. 119-124
    発行日: 1965/02/25
    公開日: 2010/02/19
    ジャーナル フリー
    For the quantitative determination of 1, 3, 4, 6-dianhydrosorbitol 2, 5-dinitrate (DSDN), the colorimetric methods by Griess-Romijn (GR) reagent and also by phenoldisulfonic acid (PDS) reagent were studied.
    The GR method is colored by the diazo reaction with GR reagent and the PDS method is colored by a formation of nitro compound with PDS reagent. The calibration curves of DSDN, measured through the filter at 530mμ of the former and at 430mμ of the latter, showed satisfactory results in the range of 47-230γ/25ml. (GR colorimetry) and of 94-550γ/25ml. (PDS colorimetry). The determination of DSDN in the preparations by both colorimetric methods was studied and the coincident result was obtained.
  • 中垣 正幸, 曾根 節子
    1965 年 85 巻 2 号 p. 125-129
    発行日: 1965/02/25
    公開日: 2010/02/19
    ジャーナル フリー
    Thermal change of equilibrium water content of polyoxyethylene series, non-ionic surfactants, toward benzene solution was studied by the double layer method at both 10° and 40° to compare them with that at 25°. The equilibrium water content of certain surfactants was similarly observed to be in a linear relation between the concentrations of surfactants and the water content in benzene layer at a certain temperature. Therefore in the similar series of surfactants, as the average molar number of ethylene oxide was larger, that is, as the HLB value was higher, the equilibrium water content showed a tendency to become larger. When an influence of temperature upon the equilibrium water content was considered, the latter increased as the temperature rose. However, the solubilization of water per mole of ethylene oxide residue was not influenced by the thermal changes. One mole of water was solubilized by about 10 moles of ethylene oxide and an increase of the equilibrium water content was explained bythe increase of the solubility of water into benzene.
  • 村山 圭介, 森村 正治, 中村 勝明, 砂川 玄俊
    1965 年 85 巻 2 号 p. 130-142
    発行日: 1965/02/25
    公開日: 2010/02/19
    ジャーナル フリー
    Utilizing the alkali ring opening reaction of 2-methyl-2-mesyloxymethylcyclopentanone by Eschenmoser, N-benzyl-2-decarboxykainic acid (XXIX) was synthesized, following to the synthetic process shown in Charts 1-C and 2. Steric configuration of 3-and 4-position of pyrrolidine ring was considered to be cis-form as α-kainic acid type. Methylation of XVII afforded 10% of XIX, subordinately, besides usual methyl derivatives (XVIII), and the once produced XVIII was considered to be transformed to XIX in the mechanism illustrated in Chart 3. From the intermediate mentioned above, pyrrolidine derivatives of XXXI, XXXIV, XXXV, XXXVII and XLI were synthesized. The compound (XXXIX), obtained in this reaction, showed the signal of ring methylene in nuclear magnetic resonance spectrum by splitting, in spite of cis-junction, and, on the contrary, singlet was appeared at τ=8.49 in cis form of 5-and 6-membered dual ring system of XLII. This is explained that the ring bond is so rigid that ring inversion becomes difficult in the cis form of 5-and 5-membered ring system.
  • 中垣 正幸, 西野 操
    1965 年 85 巻 2 号 p. 143-146
    発行日: 1965/02/25
    公開日: 2010/02/19
    ジャーナル フリー
    The effect of aluminum stearate (Al-St) on the dispersity of carbon black in benzene was studied. Channel black, furnace black and thermal black were used. Sedimentation velocity of carbon black was measured at various concentration of Al-St, and the apparent particle size was obtained according to the equation of Stokes. The concentration, required to disperse the carbon black, Cd, varied with St/Al ratio and the sort of carbon black. When St/Al ratio increased from 1 to 2, Cd decreased, but when St/Al ratio was greater than 2, it decreased for channel black, remained to be almost constant for thermal black and increased for furnace black. Flocculation of carbon black with Al-St was also observed. The concentration, Cf, at which the apparent particle size was maximum, were slightly lower than Cd. The effect of monosoap on the flocculation was greater than disoap for channel black and thermal black, but for furnace black, the particle size at Cf was about the same as that in pure benzene.
  • 小澤 光, 福田 英臣, 五味 保男, 後藤 正義, 渡辺 精子
    1965 年 85 巻 2 号 p. 147-151
    発行日: 1965/02/25
    公開日: 2010/02/19
    ジャーナル フリー
    Muscle relaxation action and anti-acetylcholine action of 7 kinds of bistetrahydroisoquinolinium derivatives and 2 kinds of decamethylene bisammonium derivatives (shown in Table I) were studied with sciatic nerve sartorius muscle preparations and rectus abdominis muscle preparations of Rana nigromaculata. Among them, 1, 8-bis (2-methyl-6, 7-methylenedioxy-1, 2, 3, 4-tetrahydroisoquinolin-1-yl) octane dimethiodide (III-V) were found to show the strongest muscle relaxation action. Their activities were in the following order, III-V, d-Tc>II>VI, VII>I, with sciatic nerve sartorius muscle preparations and III-V>VII>d-Tc>VI>II>I, with rectus abdominis muscle preparations. They showed nearly the parallel results with both preparations. As to the antagonistic action against neostigmine, K+ and acetylcholine, all of tetrahydroisoquinolinium derivatives (I-VII) showed a competitive anti-acetylcholine action, that is to say, a muscle relaxation action resembling to d-tubocurarine, however, VIII and IX were considered to possess d-tubocurarine-and succinylcholine-like actions.
  • 立松 晃, 後藤 俊夫
    1965 年 85 巻 2 号 p. 152-157
    発行日: 1965/02/25
    公開日: 2010/02/19
    ジャーナル フリー
    As one of the applications of mass spectrometry of organic compounds, an analysis of mixed medicines was attempted and various preparations were found to be easily analyzed from the characteristics of each fragment, without the interpretation of the fragmentation.
    Comparing with the usual analytical methods, mass spectrometry showed the following benefits: 1) the analysis is capable in a minute amount of 0.1-1mg. scale. 2) it can be operated within a very short period of time of 10-20min. 3) no pretreatment for the seperation is unnecessary, and 4) no indivisual error and a high reproducibility are found by the peaks correspondingto the mass numbers. Besides, 5) no influence is effected by the diluents such as starch in the preparations and by the stabilizers and preservatives in the ampoules. 6) applying the benefit of giving mass spectrum of free base, in spite of the kinds of salts.
    Therefore an identification of morphine, codeine, papaverine, thebaine, dihydrocodeine and atropine in the opium alkaloids has been studied. The quantitative treatment of hose components, according to the type analysis of the spectra, is examining.
  • 高見沢 映, 林 貞男, 佐藤 久夫
    1965 年 85 巻 2 号 p. 158-165
    発行日: 1965/02/25
    公開日: 2010/02/19
    ジャーナル フリー
    By the reaction with arylhydrazines, 2-ethoxymethyl-3-ethoxy-3-methoxypropionitrile (I), 2-methoxymethylene-3-ethoxypropionitrile (II), 2-(1-ethoxy-1-methoxymethyl) acrylonitrile (III), ethyl 2-ethoxymethyl-3-ethoxy-3-methoxypropionate (IV), and 2-methoxymethylene-3-ethoxypropionate (V) gave pyrazole derivatives similary and both 1-phenyl-2-pyrazoline-4-carbonitrile (XVIII) and ethyl 1-phenyl-2-pyrazoline-4-carboxylate (XIX) have been newly obtained from the reaction with phenylhydrazine as intermediates. In the reaction with I, o-methylsulfonylphenylhydrazine gave the corresponding 1-aryl-3-pyrazoline-4-carbonitrile (XX), and p-methylsulfonylphenylhydrazine, o- and p-tolylhydrazine produced the corresponding 1-arylpyrazole-4-carbonitrile (XXI, XXII and XXIII). In this series of reaction, when substitutional radicals of forming hydrogen bond is located at the ortho position of arylhydrazine, it will be stabilized by the production of 3-pyrazoline, and if not, 2-pyrazoline is prepared, followed by the dehydration to pyrazole. 2, 4-Dinitrophenylhydrazine and 2-methyl-3-ethoxy-3-methoxy-propionitrile (XXIV) gave 1-(2, 4-dinitrophenyl)-4-methyl-5-aminopyrazole (XXVII) and ethyl 2-methyl-3-ethoxy-3-methoxypropionate (XXVIII) gave propionaldehyde 2, 4-dinitrophenylhydrazone (XXIX).
  • 亀谷 哲治, 高野 誠一, 増子 和子, 栗原 純夫
    1965 年 85 巻 2 号 p. 166-168
    発行日: 1965/02/25
    公開日: 2010/02/19
    ジャーナル フリー
    The Arndt-Eistert reaction between 2-diazo-4′-(methylsulfonyloxy) acetophenone (VI), easily obtained from p-cresol, and methoxy-4-benzyloxyphenethylamine afforded N-(3-methoxy-4-benzyloxyphenethyl)-2-p-(methylsulfonyloxyphenyl) acetamide (VII), which was converted to 1-p-(methylsulfonyloxybenzyl)-6-methoxy-7-benzyloxy-3, 4-dihydroisoquinoline (VIII) according to the Bischler-Napieralski reaction. After the reduction of methiodide (IX) of VIII to tetrahydroisoquinoline compound (X), dl-O-benzyl-N-methylcoclaurine (XI) was derived by treating X with alkali in a good yield, considered from the starting material (VI). Further debenzylation of XI by 20% hydrochloric acid gave dl-N-methylcoclaurine (II), which was confirmed. After the reduction of VIII by zinc dust in acetic acid, a treatment with alkali and then hydrochloric acid afforded dl-coclaurine (I), which is identical with the standard sample.
  • 新田 義博, 井手 淳二
    1965 年 85 巻 2 号 p. 169-173
    発行日: 1965/02/25
    公開日: 2010/02/19
    ジャーナル フリー
    18 kinds of acetylated glucuronamide derivatives were synthesized and their infrared spectra were studied. It has been confirmed that the absorption bands of the amide I were appeared to be shifted comparatively to the higher frequency and also the charactristic absorption bands, previously reported, of α-and β-anomer of pyrannose ring were reaffirmed.
  • 新田 あや
    1965 年 85 巻 2 号 p. 173-175
    発行日: 1965/02/25
    公開日: 2010/02/19
    ジャーナル フリー
    In addition to the previously reported constituents (osthol, psoralen, isopimpinellin, byakangelicin, isobyak-angelicolic acid and so on), three coumarin derivatives (isoimperatorin, bergapten and 5-methoxy-8-hydroxypsoralen) and stigmasteryl-D-glucoside have been newly isolated from the roots of Angelica japonica.
  • 鳥越 泰義
    1965 年 85 巻 2 号 p. 176-178
    発行日: 1965/02/25
    公開日: 2010/02/19
    ジャーナル フリー
    Ursolic acid (I), n-hentriacontane (II), steryl ester (III), and β-sitosterol (IV) (contaminated with stigmasterol) were isolated from the whole herb of Plantago asiatica LINNÉ. A hydrolysis of III gave the mixture of β-sitosterol and stigmasterol as neutral components and palmitic acid as an acidic part. Therefore, the steryl ester (III) was found to be a mixture of β-sitosteryl palmitate and stigmasteryl palmitate.
  • ヒキノ ヒロシ, 曳野 靖子, 竹下 保義, 加藤 紘子, 竹本 常松
    1965 年 85 巻 2 号 p. 179-180
    発行日: 1965/02/25
    公開日: 2010/02/19
    ジャーナル フリー
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