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Volume 87, Issue 2
Displaying 1-20 of 20 articles from this issue
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Hiroyuki Inouye, Shinichi Ueda, Yuriko Araki, Hiroya Shimizu1967 Volume 87 Issue 2 Pages 109-113
Published: February 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe column chromatography with a domestic polyamide powder as an adsorption agent gave a satisfactory result for the separation of simple phenols, bromophenols, phenolic tertiary alkaloids, phenolic quaternary alkaloids, and glucosides.View full abstractDownload PDF (625K) -
Mitsuji Yanai, Toshio Kinoshita1967 Volume 87 Issue 2 Pages 114-119
Published: February 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSEther-exchange reactions using sodium methoxide or ethoxide were examined with 3-methoxy-(IXa), 3-methoxy-4-methyl-(IXb), 3-methoxy-6-chloro-(Va), 3-methoxy-4-methyl-6-chloro-(Vb), 3-ethoxy-6-chloro-(VIa), 3, 6-dimethoxy- (Ia), 3, 6-diethoxy- (IIa), and 3, 6-diethoxy-4-methylpyridazine 1-oxide (IIb), and 4-methoxy (XIIa) and 4-ethoxypyridine 1-oxide (XIIb). Ether exchange takes place under mild conditions and, dialkoxy compounds undergo hydrolysis under drastic conditions, forming hydroxy compounds (VII or VIII). In dimethoxy compounds, 3-position is more active than the 6-position, while this is reversed in diethoxy compounds. In dialkoxy compounds, methoxyl group is more sensitive to the ether exchange reaction than the ethoxyl group. 3-Alkoxy- and 3, 6-dialkoxy-pyridazine 1-oxides submit more easily to the ether exchange reaction than 3, 6-dialkoxypyridazine or 4-alkoxypyridine 1-oxide.View full abstractDownload PDF (728K) -
Matao Kanaoka, Takako Okuda, Denitsu Shiho1967 Volume 87 Issue 2 Pages 119-123
Published: February 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSIn order to obtain compounds with hypoglycemic activity, 5-mercapto- (II) and 5-amino-s-triazolo [3, 4-b] [1, 3, 4]-thiadiazoles (VIII) were synthesized by the application of carbon disulfide and cyanogen bromide to 2-hydrazino-1, 3, 4-thiadiazoles (I : R=CH3, C2H5, iso-C3H7, C6H5). By the application of methyl iodide and cyanogen bromide to the 5-mercapto compounds, in the presence of alkali, 5-methylmercapto compound (III : R'=CH3) and 5-thiocyano compound (III : R'=CN) were prepared. Oxidative chlorination of the 5-mercapto compound using chlorine gave 5-chlorosulfonyl compound which was aminated to 5-sulfamoyl compound (V). Screening of 5-sulfamoyl (V), 5-mercapto (II), and 5-thiocyano-2-isopropyl-s-triazolo [3, 4-b] [1, 3, 4]-thiadiazole (III'R=iso-C3H7 was carried out using alloxan-diabetes mice and 5-sulfamoyl and 5-mercapto compounds were found to have stronger activity than BZ-55 used as control.View full abstractDownload PDF (656K) -
Yuzo Nagase, Shigeo Baba, Akitada Matsuda1967 Volume 87 Issue 2 Pages 123-128
Published: February 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSMetabolic rate of ephedrine excretion into urine was examined by intraperitoneal injection of 14C-labeled d- and l-ephedrine into rats. Metabolic products in the urine was examined by paper chromatography combined with reverse dilution analysis. The l-compound is demethylated or hydroxylated in the p-position in vivo but the d-compound does not undergo these changes. Hippuric acid and a small amount of benzoic acid were detected besides a fair amount of nonidentified carboxylic acid and a neutral product as the metabolites.View full abstractDownload PDF (766K) -
Hideaki Shirai, Tamotsu Yashiro1967 Volume 87 Issue 2 Pages 128-132
Published: February 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSIn order to examine the antibacterial action of 2-thiohydantoin derivatives possessing-NH-CS-NH-group on tubercle bacilli, following synthesis was carried out. Thiohydantoic acid hydrazide (III) was obtained in a good yield by the reaction of 2-thiohydantoin (II) or related compounds with hydrazine hydrate. Heating of III in acetic anhydride resulted in cyclization of 1-acetyl-2-thiohydantoin (I). Condensation of III with various aromatic aldehydes gave various hydrazones. Reaction of II with phenylhydrazine or isonicotinic acid hydrazide gave 1-(4-thiohydantoinyl)-2-phenylhydrazine (XXVI) or 1-(4-thiohydantoinyl)-2-isonicotinoyl hydrazine (XXVII). XXVI and XXVII liberated II on being heated with hydrochloric acid. Growth-inhibiting action of these compounds on tubercle bacilli was examined.View full abstractDownload PDF (571K) -
Hideaki Shirai, Tamotsu Yashiro1967 Volume 87 Issue 2 Pages 133-137
Published: February 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSApplication of hydrazine hydrate to the aqueous suspension of ethyl 3-phenyl-4-thiohydantoates (IV to VI) and 1-phenyl-2-thiohydantoins (VII to IX) afforded 3-phenyl-4-thiohydantoic acid hydrazides (X to XII). When the reaction was carried out by heating in ethanol, desulfurization occurred in compounds VII to IX to produce 1-phenyl-2-hydrazinohydantoins (XVIII to XX), although the compounds IV, V, and VI reacted in the same way as above to form X, XI, and XII. Heating of X, XI, and XII in acetic anhydride resulted in their cyclization to VII, VIII, and IX, respectively. Application of several aromatic aldehydes to X and XVIII afforded hydrazones. Growth-inhibiting action of these compounds against tubercle bacilli was examined.View full abstractDownload PDF (582K) -
Hideaki Shirai, Tamotsu Yashiro1967 Volume 87 Issue 2 Pages 137-142
Published: February 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESS3-Amino-4-thiohydantoic acid hydrazide (VI) was obtained by the reaction of ethyl 3-amino-4-thiohydantoate (IV) or 1-amino-2-thiohydantoin (V) with hydrazine hydrate. Reaction of IV or V with aromatic aldehydes gave various kinds of benzylidene compounds (VII to XII or XIII to XVIII) which were reacted with hydrazine hydrate to give 3-benzylideneamino-4-thiohydantoic acid hydrazides (XIX to XXIV). Treatment of the compounds VII to XII, and XIX to XXIV with hydrochloric acid resulted in their cyclization to 1-benzylideneamino-2-thiohydantoins (XIII to XVIII). Reaction of the compounds XIX to XXIV with aromatic aldehydes afforded the corresponding hydrazones (XXV to XXVIII). Growth-inhibiting action of these 2-thiohydantoins, hydrazides, and hydrazones against tubercle bacilli was examined.View full abstractDownload PDF (625K) -
Hideaki Shirai, Tamotsu Yashiro1967 Volume 87 Issue 2 Pages 142-147
Published: February 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSStarting with 5-(p-chlorobenzylidene)-2-thiohydantoin and 5-(p-methoxybenzylidene)-2-thiohydantoin, their monoalkyl (II to IX or II' to IX') and dialkyl compounds (X to XVII) (R=CH3, C2H5, n-C3H7, n-C4H9) were prepared. Heating of these compounds with conc. hydrochloric acid afforded 3-alkyl-5-benzylidenehydantoins (XVIII to XXVII), and reaction with acetic anhydride have acetylated compounds (XXVIII to XXXI). Reaction with hydrazine hydrate afforded hydrazino compounds (XXXIV to XXXVII). Reaction with phenylhydrazine and some amines was also carried out and 2-substituted compounds (XL to XLIII) were prepared. Growth-inhibiting action of these compounds against tubercle bacclli was examined.View full abstractDownload PDF (650K) -
Koji Kuroda, Genzo Hashizume1967 Volume 87 Issue 2 Pages 148-158
Published: February 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSIn order to utilize the X-ray diffraction method for the determination of crystalline component in ointments, determination of boric acid and zinc oxide was carried out on various ointments having white petrolatum as the ointment base, since approximation of its mass absorption coefficient can be calculated, and containing boric acid and zinc oxide as the chief components since these are used frequently. The method of determination used both the direct and internal standard (magnesium oxide) methods. It was thereby found that this method is quite practicable. The largest factor that caused the greatest scattering of the values in diffraction intensity was found to be the method of fixing the sample to the holder. Determination error by this method is greater than that by the method stipulated by the Japanese Pharmacopoeia, but the method is advantageous in several respects such as no necessity for extraction, comparatively short period of the whole procedure, and small amount of sample necessary.View full abstractDownload PDF (975K) -
Koji Kuroda, Genzo Hashizume1967 Volume 87 Issue 2 Pages 159-163
Published: February 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSDetermination of the chief components in an ointment was carried out on various ointments having white petrolatum as the base and containing salicylic acid, ethyl aminobenzoate, and/or sulfisomidine, employing the X-ray diffraction by the direct method and by the internal standard method using magnesium oxide as the standard. The mass absorption coefficient, μ, of these main components is approximately the same as that of the base, and the concentration of the chief component and intensity of the diffraction lines in the direct method were approximately linear. Determination of these ointments by the X-ray diffraction method seems to be practicable.View full abstractDownload PDF (505K) -
Chihoko Iijima1967 Volume 87 Issue 2 Pages 164-167
Published: February 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSIn the reaction of quinoxaline 1-oxide (I) and phenyl isocyanate, 2-anilinoquinoxaline (II), 1, 3-diphenyl-1-(2-quinoxalinyl) urea (III), and 1, 3-diphenyl-1H-imidazo [4, 5-b] quinoxalin-2 (3H)-one (VI) are obtained according to reaction conditions. This reaction course was explained as shown in Chart 2.View full abstractDownload PDF (510K) -
Tetsuji Kametani, Isao Noguchi, Seiichi Nakamura, Yutaka Konno1967 Volume 87 Issue 2 Pages 168-173
Published: February 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESS7-Benzyloxy-1-(3, 4-bisbenzyloxybenzyl)-6-methoxy-1, 2, 3, 4-tetrahydroisoquinoline (XIV) was submitted to the Eschweiler-Clarke reaction in 98% formic acid and 37% formaldehyde solution, and 7-benzyloxy-1-(3, 4-bisbenzyloxybenzyl)-6-methoxy-2-methyl-1, 2, 3, 4-tetrahydroisoquinoline (XV) was obtained in 5.9% yield, with trans-2, 10, 11-trisbenzyloxy-3-methoxy-5, 6, 13, 13a-tetrahydro-8H-dibenzo-[a, g] quinolizine (XVI) in 80.4% yield. XVI was also obtained in 83.1% yield by refluxing XIV in a mixture of acetic acid and 37% formaldehyde solution, and dehydrogenation of XVI with mercuric acetate gave a quarternary ammonium salt (XIX). Debenzylation of XVI in ethanolic hydrochloric acid gave (±)-O-demethylcoreximine (XVII) whose methylation with diazomethane gave (±)-norcoralydine (XVIII), which was identified with an authentic sample through admixture, infrared spectra, and by thinlayer chromatography.View full abstractDownload PDF (761K) -
Tetsuji Kametani, Masataka Ihara1967 Volume 87 Issue 2 Pages 174-178
Published: February 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESS1-(3-Benzyloxy-4-methoxybenzyl)-6-methoxy-7-benzyloxy-1, 2, 3, 4-tetrahydroisoquinoline (VI) and 1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-7-hydroxy-1, 2, 3, 4-tetrahydroisoquinoline (VII) were synthesized according to the route shown in Chart 1. VI and VII were reacted with formic acid or acetic acid to obtain respectively (±)-O, O-dibenzylcoreximine (IX) and (±)-coreximine (VIII). At the same time, (±)-norcoralydine (X) was prepared from (±)-norlaudanosine (XII) under the same condition and X was identified with (±)-norcoralydine derived from (±)-coreximine. Norcoralydine was found to occur in dimorphic forms of granular crystals (Xa) of m.p. 145∼145.5° and prismatic crystals (Xb) of m.p. 155°.View full abstractDownload PDF (674K) -
Tetsuji Kametani, Mitsuo Satoh1967 Volume 87 Issue 2 Pages 179-184
Published: February 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe 3, 4-dihydroisoquinoline compound (XII), obtained by the Bischler-Napieralski reaction of the amide (XI), was derived to the 1, 2, 3, 4-tetrahydroisoquinoline compound (XIII) and debenzylated to 1-(4-hydroxy-3-methoxybenzyl)-6-methoxy-1, 2, 3, 4-tetrahydroisoquinolin-7-ol (II). The free base of XII was very labile and easily changed to 1-benzoylisoquinoline (XIV) which was submitted to the Clemmensen reduction to obtain II. In order to obtain 1-(4-hydroxy-3-methoxybenzyl)-6-methoxy-2-methyl-7-hydroxy-1, 2, 3, 4-tetrahydroisoquinoline (I), II was submitted to the Eschweiler-Clarke reaction and an unexpected cyclization to the dibenzoquinolizine base occurred, forming XV, a kind of isomer of coreximine. Methylation of XV with diazomethane gave (±)-norcoralydine (XVI), while treatment of II with sodium borohydride and formaldehyde solution resulted in normal N-methylation to form I.View full abstractDownload PDF (766K) -
Shoji Toyoshima, Katsutoshi Shimada, Kiyoshi Kawabe1967 Volume 87 Issue 2 Pages 184-191
Published: February 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSStarting with alkyl 5-nitro-2-furan acrylimidate hydrochloride (II), N-acetamido-(5-nitro-2-furyl) acrylimidic acid (IV) (Table I), 2-[2-(5-nitro-2-furyl) vinyl]-(5-substituted)-1, 3, 4-oxa (or thia) diazoles (V) (Table II), 2-[2-(5-nitro-2-furyl) vinyl]-(5-substituted)-benzimida (or oxa, thia) zoles (VII) (Table III), and other derivatives (IX, X) (Table IV) were synthesized. Antibacterial action of these derivatives in vitro was examined and the results are listed in Table V.View full abstractDownload PDF (744K) -
Tetsuji Kametani, Seiichi Takano, Fujinori Sasaki1967 Volume 87 Issue 2 Pages 191-195
Published: February 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSBoiling of 1-substituted 6, 7-dimethoxy-3, 4-dihydroisoquinoline derivatives (X and XII) in constant-boiling point hydrochloric acid at ordinary pressure, in nitrogen stream, for 50 hours resulted chiefly in selective demethylation of the methoxyl at 7-position to form the compounds XI and XIII, respectively. On the other hand, treatment of X and XII with metallic sodium or with metallic lithium and liquid ammonia resulted in selective demethylation of the methoxyl in 6-position, with concurrent reduction of the C=N bond to form dl-salsoline (XVI) and the compound (XVIII).View full abstractDownload PDF (667K) -
Tetsuji Kametani, Shiroshi Shibuya1967 Volume 87 Issue 2 Pages 196-198
Published: February 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSCularimine (I) has been synthesized from a dicarboxylic acid (II) through four steps and examinations were made on an improved method for the synthesis of II. It was thereby found that reduction of the dialdehyde compound (III) with sodium borohydride to the alcohol (IV), its conversion to the nitrile (VI) through V, and hydrolysis of VI gave II in a good yield. This increased the total yield of I over that already reported. Optical resolution of (±)-cularimine using di-p-toluoyl tartaric acid was found to give the two optically active cularimines.View full abstractDownload PDF (456K) -
Tetsuji Kametani, Shiroshi Shibuya, Shinichi Sasaki1967 Volume 87 Issue 2 Pages 198-201
Published: February 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSDemethylation of 10-oxo-oxepine compound (VI) resulted in the cleavage of the three methoxyl groups to produce 2, 3, 6-trihydroxy compound (VII). By utilizing this reaction, attempt was made to obtain cularicine (I) by the preparation of O, O, O-desmethylcularine (II) and O, O, O-desmethylcularimine (III), and demethylation of cularine (IV) and cularimine (V) was carried out. However, in place of the expected II and III, phenolic bases (X and XI) possessing one methoxyl group were obtained. The remaining methoxyl group was found to correspond to that in the 9-position of IV and V through NMR spectral measurements, and it was concluded that the methoxyl groups in 6- and 10-positions were selectively cleaved by demethylation.View full abstractDownload PDF (513K) -
Koji Kuroda, Genzo Hashizume1967 Volume 87 Issue 2 Pages 202-207
Published: February 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSQuantitative determination was carried out on ointments (HPV and SV), which had white petrolatum (V) as the base and mercurous chloride (HP) or sulfurs as the chief constituent, as examples of an ointment using a chief constituent with greater coefficient of mass absorption, μ, than that of the ointment base. The determination was made by the X-ray diffraction method (direct method and the internal standard method using magnesium oxide as the standard). The direct method was found to give values with less reliability since the relationship between concentration and intensity of diffraction lines gave a bent curve, and the internal standard method seemed to be better in this case. The X-ray diffraction method, however, seemed to be practicable for determination.View full abstractDownload PDF (625K) -
Masashi Tomoda1967 Volume 87 Issue 2 Pages 207-209
Published: February 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSSeparation of monosaccharides was attempted by thin-layer chromatography over cellulose, using various solvents and the results obtained are listed in Table I. The most effective procedure for general analysis of monosaccharides was found to be the combined use of a solvent system of butanol-pyridine-acetic acid-water (10 : 6 : 1 : 3), ethyl acetate-pyridine-water (10 : 3 : 2), or ethyl acetate-isopropanol-pyridine-water (7 : 3 : 2 : 2) with phenol-1% ammonia water (2 : 1).View full abstractDownload PDF (441K)
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