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大和 正利, 北村 武夫, 橋垣 国子, 桑野 泰代, 芳田 典子, 小山 鷹二
1972 年 92 巻 4 号 p.
367-370
発行日: 1972/04/25
公開日: 2008/05/30
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The present studies were undertaken to elucidate the relationship between sweetness and chemical structure because of the interest of the structure of phyllodulcin, the only sweettasting compound among 3, 4-dihydroisocoumarins. 3, 4-Dihydroisocoumarin derivative, in which the 3'-hydroxy and 4'-methoxy groups bonded to the phenyl group in 3-position of phyllodulcin are present individually, had no sweetness. The presence of these hydroxyl and methoxyl in adjacent positions is necessary for the appearance of sweetness. Further, sweet taste is not found in the compound if the positions of these two groups are reversed. It was found by the syntheses of various derivatives that the lactone group and a hydroxyl group in 8-position did not take part in the appearance of sweet taste.
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田村 恭光, 須本 国弘, 真野 光彦, 増井 武彦
1972 年 92 巻 4 号 p.
371-374
発行日: 1972/04/25
公開日: 2008/05/30
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Reactions of N-(2, 4-dinitrophenyl) pyridinium chloride (I) with five active methylene compounds were found to proceed by the following three routes. Malonodinitrile and ethyl cyanoacetate attacked the α-position of the pyridine ring in I, resulting in the rupture of a C-N bond, and thus gave 1-(2, 4-dinitroanilino)-6, 6-dicyano-1, 3, 5-hexatriene (II) and 1-(2, 4-dinitroanilino)-6-ethoxycarbonyl-6-cyano-1, 3, 5-hexatriene (III). Diethyl malonate and malonodiamide added at γ-position of the pyridine ring to give N-(2, 4-dinitrophenyl)-4-diethoxycarbonylmethyl-1, 4-dihydropyridine (V) and N-(2, 4-dinitrophenyl)-4-dicarbamoylmethyl-1, 4-dihydropyridine (VI). Cyanoacetamide added at α-position of the pyridine ring to give N-(2, 4-dinitrophenyl)-2-(α-carbamoyl) cyanomethyl-1, 2-dihydropyridine (VII).
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中西 美智夫, 今村 博, 中村 忠男, 木村 智彦
1972 年 92 巻 4 号 p.
375-383
発行日: 1972/04/25
公開日: 2008/05/30
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フリー
1-tert-Butylamino-3-[o-(tetrahydrofurfuryloxy) phenoxy]-2-propanol hydrochloride (Y-6124) antagonizes the adrenergic β-receptor stimulating action of isoproterenol or of epinephrine in the isolated atrial preparation of guinea pigs or in the isolated uterus preparation of a rat. In the open-chest dog, Y-6124 administered intravenously showed more potent activities than propranolol in inhibiting responses, especially heart rate increase, induced by isoproterenol or epinephrine, or by electrical stimulation of stellate ganglion. By oral administration, Y-6124 in such a low dose as 0.1 mg/kg, inhibited responses induced by isoproterenol. The compound had more potent inhibiting activities than propranolol on blood flow in the coronary artery or in the femoral artery of the anesthetized dog by intraarterial administration. Y-6124, like propranolol, may be a compound having a potent adrenergic β-receptor blocking activity but no stimulating action on the receptor.
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灘井 種一, 西井 絹代, 立松 晃
1972 年 92 巻 4 号 p.
384-387
発行日: 1972/04/25
公開日: 2008/05/30
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The effect of tetracycline on the intestinal absorption of other co-existing drugs was investigated by the recirculation and the loop methods in the rat. It was found that, at pH 8.0, the absorption of sulfaguanidine, a poorly absorbable drug having no interaction with tetracycline, increased to a considerable extent in the presence of tetracycline. At pH 6.0, however, any noticeable change was not recognized. As regards sulfamine, known as a moderately absorbable drug, similar effect was not observed at pH 8.0 and 6.0. The absorption enhancement effect of demethylchlortetracycline, methyleneoxytetracycline, and oxytetracycline was also examined by similar methods. It was found that, at pH 6.0 and 8.0, these drugs except oxytetracycline exerted enhancing effect on the absorption of poorly absorbable drugs.
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灘井 種一, 西井 絹代, 立松 晃
1972 年 92 巻 4 号 p.
388-392
発行日: 1972/04/25
公開日: 2008/05/30
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フリー
Sulfanilic acid or sulfaguanidine was injected as a marker drug intravenously into the rat, the small intestine was perfused with either tetracycline solution or isotonic buffer solution, and the amount of injected drugs exsorbed to the perfused solution was examined. This procedure excludes any interaction between tetracycline and the marker drugs and is sensitive enough to detect any permeability change caused by the former drug. It was found that the exsorption of marker drugs increased to a considerable extent in the case of tetracycline at pH 8.0, which agreed with the result of a previous experiment on enhancement of intestinal absorption of sulfa drugs in the presence of tetracycline. This effect of tetracycline is attributable to its influence on the small intestinal tissue.
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高橋 昭江, 渡辺 光夫, 朝比奈 正人, 山羽 力
1972 年 92 巻 4 号 p.
393-396
発行日: 1972/04/25
公開日: 2008/05/30
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フリー
A method for fluorometric determination of cyclohexylamine, a metabolite of cyclamate, in biological samples was devised. Cyclohexylamine was extracted with 5 ml of chloroform from 3-5 ml of the sample (urine, blood, or tissue homogenates) basified to pH 13 with 6 N NaOH. Then, 4 ml of the chloroform layer was shaken with 4 ml of 0.5 N HCl. To 1 ml of the aqueous layer, 0.08 ml of 6 N NaOH, 0.92 ml of water, 2 ml of 0.5% 1-dimethyl-aminonaphthalene-5-sulfonyl chloride in acetone, and 1 ml of 5% NaHCO
3 were added. The sample was kept at a room tempeature overnight, and shaken with 5 ml of chloroform. After 6 ml of the chloroform-acetone layer was concentrated in vacuo, the volume was adjusted to 1.5 ml with acetone. Then, 0.1 ml of the concentrate was spotted on silica gel plate and developed with a mixture of benzene : acetone (20 : 1). A yellow fluorescent spot (Rf 0.6) was extracted with 4 ml of dioxane and fluorescence (ex. 360 mμ, fl. 490 mμ, excited with Hg lamp) was estimated. The standard curve was linear within the range of 0.5-5 μg/ml and the recovery from urine, blood, or tissue homogenates of guinea pig and human urine was satisfactory.
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染井 正徳, 岡本 敏彦
1972 年 92 巻 4 号 p.
397-410
発行日: 1972/04/25
公開日: 2008/05/30
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フリー
On the assumption that non-activated C-H bond should be functionalized by the photolysis of some nitrones, the nitrone [24] derived from Enmein [1] in 14 steps was photodecomposed under various conditions, and the expected products [25 and 26] were obtained in a favorable yield. The structure of the compound [25] was determined unequivocally, and the possible mechanisms (d and e) (Fig. 4) were presumed. The compound [25] was then converted into gibberellin A
15 in 6 steps. The route of [41]→[43]+[44] seems to be interesting, suggesting the biogenesis of gibberellin from kaurene.
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中野 三郎, 谷口 寛一, 古橋 崇子
1972 年 92 巻 4 号 p.
411-416
発行日: 1972/04/25
公開日: 2008/05/30
ジャーナル
フリー
Fluorometric determination of thonzylamine hydrochloride (I) with o-aminothiophenol (II) was investigated. Previous to the determination of I, determination of p-anisaldehyde (III) with II was devised. The reaction for the determination of I involved the oxidation of I by NaIO
4 to produce III and fluorescence reaction of III with II. The fluorescent substance formed by this reaction was found to be 2-(4-methoxyphenyl) benzothiazole (IV) from its spectroscopic and fluorometric analysis. Fluorescence characteristics of IV in various media were examined, and it was found that IV exhibited the strongest fluorescence in an acid solution of pH below 0.35. Based on this fact, fluorometric determination of III and I with II was established. The recommended analytical procedure for I is as follows : To 5 ml of a sample solution containing 0.5-50 μg of I, 5 ml of 10% (w/v) Na
2CO
3 and 0.5 ml of 0.1% NaIO
4 are added, warmed for 15 minutes in a boiling water bath, and the reaction product is extracted with 10 ml of ether. The ether layer is washed twice with 5 ml of water, 1 ml of 0.5% II-hydrochloride is added, ether is evaporated, and 5 ml of 30% (w/v) H
2SO
4 is added to the residue. The mixture is heated for 1 hour, cooled, diluted to 20 ml with water, and the fluorescence of this solution with the maximum 412 mμ is measured. By this method, 0.1-10 μg of I per ml can be determined. Procedure for the determination of III is identical with the reaction of oxidation product of I with II in the procedure for I, and 0.1-1.0 μg of III per ml can be determined.
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古川 淳, 渡辺 三明
1972 年 92 巻 4 号 p.
417-420
発行日: 1972/04/25
公開日: 2008/05/30
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フリー
3-Phenacylidenebenzothiophen-2-one (IIIa) was obtained in a good yield by the application of triphenylphosphinebenzoylmethylene (IIa) to thionaphthenequinone (I). The reduction of IIIa with Na
2S
2O
4 in EtOH-H
2O produced the corresponding dihydro compounds (IV) (enol form) and (V) (keto form). Reaction of IV and V with hydrazine hydrate in AcOH afforded 3-phenylthianaphtheno [2, 3-c] pyridazine (VII).
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亀谷 哲治, 気賀沢 和雄, 柊木 峯治, 脇坂 菊雄, 瓜生 恒夫, 林 恵美子
1972 年 92 巻 4 号 p.
421-430
発行日: 1972/04/25
公開日: 2008/05/30
ジャーナル
フリー
In order to obtain an effective analgesic agent, 4-amino-3-methyl-1, 2-diphenylbutane derivatives were synthesized. These compounds, the structure of which are similar to propoxyphene, have hydroxyl, methoxyl, benzyloxyl, or acyloxy group in the benzene ring and dimethylamino, 1-piperidino, diallylamino, or benzylamino group as a basic function. Further, two kinds of diastereoisomers were separated by column chromatography or fractional crystallization. Structure of these compounds was confirmed by spectral data.
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亀谷 哲治, 気賀沢 和雄, 柊木 峯治, 石丸 晴英, 斎藤 節
1972 年 92 巻 4 号 p.
431-436
発行日: 1972/04/25
公開日: 2008/05/30
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フリー
In order to examine their effect on carragenin-induced edema in rats, N-(2-aminoethyl)-, N-[2-(2, 3-xylidino) ethyl]-, N-[2-phenylacetamidoethyl]-, N-[2-(1-piperidino) ethyl]-, and N-[2-(4-morpholino) ethyl]-2-indanamines were synthesized. Several compounds showed anti-inflammatory effect comparable to that of mefenamic acid.
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篠田 雅人, 清水 節子, 高木 良成, 赤星 三弥
1972 年 92 巻 4 号 p.
437-441
発行日: 1972/04/25
公開日: 2008/05/30
ジャーナル
フリー
Examinations were made on the method of potency test for radiation protective agents, using S-(2-aminoethyl) isothiuronium bromide hydrobromide and 2-mercaptoethylamine, with decrease in body weight of mice by X-ray irradiation as an indicator. The effective method was found to be the use of ddY male mice as the experimental animal, with a X-ray dose of 400-600 R, and measuring variation in body weight during two weeks after irradiation, by which significant protective effect was found against body weight decrease.
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篠田 雅人, 清水 節子, 日野 亨, 玉置 文一, 赤星 三弥
1972 年 92 巻 4 号 p.
442-448
発行日: 1972/04/25
公開日: 2008/05/30
ジャーナル
フリー
Toxicity and radiation protective activity were examined with mice on 29 kinds of substances including N- or N'-alkylated derivatives (AET-type compounds) of S, 2-aminoethylisothiuronium bromide hydrobromide, guanidinoethyl disulfide-type compounds (GED-type compounds) obtained from AET-type compounds by transguanylation and oxidation, and 2-aminothiazoline-type (2-AT-type) compounds obtained by cyclization and deammoniation of 2-AT-type compounds. N-Methyl-AET and N'-methyl-AET compounds showed the same potency as the AET compounds but other compounds of the AET type had much less efficacy. Dialkylation of N or N' position in AET compounds totally abolished the effect. AET and GED compounds showed about the same potency. 2-AT-type compounds generally had an effect though weak.
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小林 五郎, 松田 芳郎, 夏木 令子, 山口 博之, 富永 義則
1972 年 92 巻 4 号 p.
449-453
発行日: 1972/04/25
公開日: 2008/05/30
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フリー
Application of carbon disulfide to o-methoxycarbonylphenylacetonitrile (Ia) or dimethyl homophthalate (Ib), in the presence of sodium hydride, affords mercaptothioisocoumarins (IIa, b). Reaction of Ia or Ib with carbon disulfide and dimethyl sulfate, in the presence of sodium hydride, gives 3-methylthioisocoumarins (IIIa, b). In the reaction of IIIa and amines, 3-aziridino-4-cyanothioisocoumarins (IV and V) are formed from IIIa and diethylaminoethylamine or aminoacetal, while cleavage of the thioisocoumarin ring occurs in the reaction of IIIa and hydrazine hydrate. This cleaved compound (VI) changed to cyclized products (VII and VIII) on being treated with acetone or by methylation. Reaction of IIIa with secondary amines (morpholine, piperidine, and pyrrolidine) resulted in exchange of methylthio group with amino group, with further addition of 1 mole of the amine to the cyano group, producing 4-iminothioisocoumarins (XII).
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伊坂 一郎, 柏木 輝也, 中野 功二, 川原 紀夫, 甲田 彰男, 沼崎 洋三, 河原 茂実, 村上 増雄
1972 年 92 巻 4 号 p.
454-458
発行日: 1972/04/25
公開日: 2008/05/30
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フリー
3, 5-Di-tert-butyl-4-hydroxybenzyl benzylpenicillinate (IV) and trityl benzylpenicillinate (IX) were synthesised as a valuable intermediate in the chemical preparation of semisynthetic penicillins. These benzylpenicillin esters were treated with PCl
5 and followed by methanol to form iminoethers. The iminoether (VI) derived from IV was allowed to react with 3-o-chloroplienyl-5-methylisoxazole-4-carbonyl chloride directly affording 3', 5'-di-tert-butyl-4'-hydroxybenzyl 3-o-chlorophenyl-5-methyl-4-isoxazolyl-penicillinate (VII) which was converted to cloxacillin (VIII) under mild basic conditions. The reaction of the iminoether derived from IX with D (-)-α-phenylglycyl chloride hydrochloride afforded α-aminobenzylpenicillin (X) after treatment of the reaction mixture with water. Several other semisynthetic penicillins were also obtained from IV and IX by this new procedure.
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甲田 彰男, 高信 清, 伊坂 一郎, 柏木 輝也, 高橋 孝三, 河原 茂実, 村上 増雄
1972 年 92 巻 4 号 p.
459-464
発行日: 1972/04/25
公開日: 2008/05/30
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フリー
Examinations were made on the mechanism of the reaction of iminoethers derived from benzylpenicillin esters with acid chloride. Slow addition of N-phenylformimino methyl ether (IIIb) to benzoyl chloride (IVb) afforded N-formylbenzanilide (VIb), but N-[1-(N-formyl-N-phenylamino)-1-methoxymethyl] benzanilide (VIIIb) was obtained as a main product when the latter was added to the former. These results suggested the formation of an addition compound (V) of iminoether and acid chloride. Nuclear magnetic resonance (NMR) of the reaction mixture of N-phenylformimino ethyl ether (IIIc) and phenylacetyl chloride (IVc) at-40° also showed the formation of a similar intermediate (V) which was converted to phenylacetanilide (Xc) and orthoformate (IXc) by the action of methanol. The iminoether (XIII) of methyl benzylpenicillinate (XII) was allowed to react with D (-)-α-phenylglycyl chloride hydrochloride (XIV) affording methyl α-aminobenzylpenicillinate (XVI). Follow-up of the reaction by IR and NMR indicated the direct reaction of iminoether (XIII) with acid chloride as is the case with N-phenylformimino ethers (III).
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小嶋 正治, 川北 武志, 工藤 恵子
1972 年 92 巻 4 号 p.
465-470
発行日: 1972/04/25
公開日: 2008/05/30
ジャーナル
フリー
1-p-Tolylsulfonyl-or benzylsulfonyl-aziridine (Ia or b) reacted with sodium ethyl malonate in ethanol or benzene to produce ethyl 1-p-tolylsulfonyl-or benzylsulfonyl-2-oxo-3-pyrrolidinecarboxylate (IIa or b). On the other hand, in diethyl carbonate, 2, 7-bis (benzylsulfonyl)-2, 7-diazaspiro [4, 4] nonane-1, 6-dione (VIII) was obtained from Ib. Reaction of Ia and b with sodium ethyl acetoacetate also produced 1-p-tolylsulfonyl-or benzylsulfonyl-3-acetyl-2-pyrrolidinone (XIa or b) but, with sodium ethyl cyanoacetate, the expected products were not obtained. The benzylsulfonyl group in II, VIII, and XI was more easily removed by heating with Raney nickel in ethanol than the p-tolylsulfonyl group to the corresponding pyrrolidinone derivatives.
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小澤 光, 桂木 猛
1972 年 92 巻 4 号 p.
471-478
発行日: 1972/04/25
公開日: 2008/05/30
ジャーナル
フリー
Aminoguanidines and triazoles were synthesized and their general pharmacological actions were examined. Test compounds were benzoyl-(I), 3-hydroxy-4, 5-dimethoxybenzoyl-(II), 3-benzyloxy-4, 5-dimethoxybenzoyl-(III), 3, 4, 5-trimethoxybenzoyl-(IV), nicotinoyl-(V), isonicotinoyl-(VI), 3, 4-dihydroxy-5-methoxybenzoyl aminoguanidines (X) and 3-phenyl-(VII), 3-(3'-pyridyl)-(VIII), and 3-(4'-pyridyl)-5-amino-1, 2, 4-triazoles (IX). Among these compounds, II, III, and X showed interesting pharmacological actions. II produced a contractile response in the small intestine of a mouse, which was inhibited by procaine and atropine but not by hexamethonium or morphine, while the response was potentiated by a cholinesterase inhibitor. Therefore, II possesses a muscarinic property. However, the nicotinic action did not appear. III showed a papaverine-like action ; contraction of the small intestine evoked by ACh and BaCl
2 was surpressed by III. III showed the anti-Ba
2+ action half as potent as papaverine. On the rat blood pressure, X had a potent presser action which was blocked by phentolamine. Also, a positive inotropic action appeared on the isolated rat heart. With the exception of X, a correlation of the pharmacological activity with acute toxicity of the test compounds was observed in this experiment.
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ヒキノ ヒロシ, 小野 雅康, 竹本 常松
1972 年 92 巻 4 号 p.
479-481
発行日: 1972/04/25
公開日: 2008/05/30
ジャーナル
フリー
In the survey of the root constituents of a valerian indigenous to Mt. Tate-yama, central Honshu, a number of sesquiterpenoids have been isolated or detected. This valerian is characterized by containing 8-epi-kessanol, a kessane derivative oxygenated at 8α-position, in a large quantity.
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藤田 路一, 糸川 秀治, 井上(旧姓岡) 順子, 野津 芳正, 後藤 夏江, 長谷川 和子
1972 年 92 巻 4 号 p.
482-489
発行日: 1972/04/25
公開日: 2008/05/30
ジャーナル
フリー
From Lophophora williamsii var. caespitosa, pellotine, anhalidine, anhalonidine, and anhalamine were obtained as phenolic alkaloids, and lophophorine was isolated as a nonphenolic alkaloid, which all belong to the tetrahydroisoquinoline system. A kind of betaine-type yellow components, anhalotine (=Y
1=I), Y
2 (II), Y
3 (III), and peyotine (=Y
4=IV) were isolated. They were the derivatives of 6, 7-dimethoxy-3, 4-dihydro-8-hydroxy isoquinolinium innersalt. Similar types of tautomerism were found in I and IV, and they had pKa 6.0 and 6.5, respectively. Another type of tautomerism was found in II and III. II had pKa
1 5.6 and pKa
2 10.9, and III had pKa
1 6.7 and pKa
2 11.4.
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我謝 充弘, 辻 明良, 桜井 洋二郎, 来海 正輝, 遠藤 武, 佐藤 重男, 山口 一孝
1972 年 92 巻 4 号 p.
490-497
発行日: 1972/04/25
公開日: 2008/05/30
ジャーナル
フリー
A number of phenylacrolein, furylacrolein, benzaldehyde and furfural derivatives, including their α-bromides, were synthesized. Further, their condensation products with rhodanines and 5-oxothiazolidine-2-thione were synthesized. The in vitro antimicrobial activity of these compounds (76 compounds in all) was also determined. 1) Introduction of bromine into α-position of these compounds, particularly in a series of phenylacrolein derivatives, and of NO
2 group into 5-position of the furylacrolein derivatives significantly increased the antimicrobial activity. 2) Some benzylidene derivatives of rhodanines and of 5-oxothiazolidine-2-thione were found to be active against Trichophyton, whereas those of phenylacrylidene derivatives were found to be inactive.
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ヒキノ ヒロシ, 曳野 靖子, 中村 れい子, 小野 雅康, 竹本 常松
1972 年 92 巻 4 号 p.
498-502
発行日: 1972/04/25
公開日: 2008/05/30
ジャーナル
フリー
By the examination of the root constituents of a valerian indigenous to Mt. Kongo, central Honshu, a number of sesquiterpenoids were isolated or detected. This valerian is similar in components to certain cultivated Japanese valerians (Hokkai-kisso, etc), but is characterized by containing eudesm-11-en-4α-ol (kongol). This sesquiterpenoid is the first example possessing 14β, 15β-dimethyl arrangement as valerian constituents.
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堀井 善一, 伯水 英夫, 重内 利明, 花岡 美代次, 百瀬 雄章
1972 年 92 巻 4 号 p.
503-506
発行日: 1972/04/25
公開日: 2008/05/30
ジャーナル
フリー
Methyl 2-(1-acetoxy-3-oxobutyl) phenylacetate (XII) and 2-(3-oxobutyl) phenylacetonitrile (XVIII), the model intermediates for the construction of the AB-ring system in anthracyclinones, were synthesized. Attempted cyclization of XII and XVIII under the condition according to the Brockmann's procedure was unsuccessful.
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嶋 剋人, 久田 末雄, 稲垣 勲
1972 年 92 巻 4 号 p.
507-509
発行日: 1972/04/25
公開日: 2008/05/30
ジャーナル
フリー
The methanol extract of the leaves of Anodendron affine DURCE was treated as shown in Chart 1. Three compounds were isolated from the parts [A and B] soluble in ethyl acetate and the extract [C] with chloroform-methanol (2 : 1). These were identified as kaempferol (I), astragalin (II), and dambonitol (III) by thin-layer chromatography, infrared, ultraviolet and mixed melting point.
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田中 悟, 若林 庸夫, 橋本 和典, 豊島 昭二
1972 年 92 巻 4 号 p.
510-513
発行日: 1972/04/25
公開日: 2008/05/30
ジャーナル
フリー
A new quaternary bases of tropine tropate were synthesized by the route shown in Table I and its anticholinergic and antibarium actions were examined with excised mouse intestine. Antispasmotic action of these compounds is summarized in Table II. A considerable number of these compounds showed stronger and more lasting anticholinergic and antibarium actions than hyoscine butyl bromide used as a control.
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富松 祥郎, 坂本 正徳
1972 年 92 巻 4 号 p.
514-516
発行日: 1972/04/25
公開日: 2008/05/30
ジャーナル
フリー
Spectroscopic and chemical reinvestigation on the structure of the product obtained from the reaction of N, N'-bis (p-dimethylaminophenyl) ethylenediimine (I) with p-benzoquinone revealed that the product was not the Diels-Alder type adduct (III) assigned previously but an equimolar complex of I and hydroquione.
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渡辺 敬三, 牧野 由紀子, 岡本 敏彦
1972 年 92 巻 4 号 p.
517-519
発行日: 1972/04/25
公開日: 2008/05/30
ジャーナル
フリー