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YOSHINORI KIDANI, KENJI INAGAKI, HISASHI KOIKE
1973 Volume 93 Issue 9 Pages
1089-1093
Published: September 25, 1973
Released on J-STAGE: May 30, 2008
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Acid dissociation constant (pK
a) of 1-hydroxyphenazine and stability constants of its metal complexes with bivalent metals such as Cu, Ni, Co, Zn, and Cd were determined by spectrophotometry in 50% (v/v) ethanol. It was found that pK
a of 1-hydroxyphenazine was 9.21 and stability constants of these complexes were similar to those of 5-hydroxyquinoxaline-metal complexes, being smaller than those of 8-hydroxyquinoline-metal complexes. The binding ratio of 1-hydroxyphenazine-metal complexes was 2 : 1 from elemental analyses and mass spectrum. In its mass spectrum, the fragmentation of these 2 : 1 metal complexes was in good agreement with those of 8-hydroxyquinoline-metal complexes.
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TETSUJI KAMETANI, KEIICHIRO FUKUMOTO, YASUYUKI KATO, MICHIO FUJIHARA
1973 Volume 93 Issue 9 Pages
1094-1099
Published: September 25, 1973
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Treatment of 1-benzyloxy-2, 11-dimethoxy-5, 5a, 6, 7, 8-pentahydrobenzo [b] oxepino-[7, 6, 5-ij] isoquinoline (XVI) or its derivative (XV) with some oxidative reagents resulted in the formation of only 1-benzyloxy-2, 11-dimethoxy-5-oxobenzo [b] oxepino [7, 6, 5-ij] isoquinoline (XX) or its derivative (XXI).
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YOSHIHARU TAKAI, KENJI NAITO, JINSAKU SAKAKIBARA, MASAITI YASUE
1973 Volume 93 Issue 9 Pages
1100-1104
Published: September 25, 1973
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N-Methylacetanilide did not react on Friedel-Crafts acylation but did afford o- and p-nitro compounds (ortho : para ratio, 1 : 6) on mixed acid nitration. Nitration with copper nitrate and acetic anhydride furnished only the p-nitro compound rather than the o-nitro compound as reported previously in the nitration of acetanilide. The bromination of N-methylacetanilide with bromine in acetic acid occurred at para-position as in acetanilide but there precipitated an orange crystals which were an addition compound composed of two moles of p-bromo-N-methylacetanilide and one mole each of bromine and hydrogen bromide (p-BrC
6H
4N(CH
3)Ac)
2·HBr
3. Several N-methylacetanilide derivatives were synthesized and tested for the formation of bromine addition compounds. When N-methylacetamide group in benzene ring is one, composition of the addition compounds is A
2HBr
3 (where A represents the N-methylacetanilide derivative), but when two, the composition is A·HBr
3 (Fig. 2), similar to that of pyridinium bromide perbromide (C
5H
5N·HBr)
3.
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MASAYUKI NAKAGAKI, KENJI MIYATA
1973 Volume 93 Issue 9 Pages
1105-1111
Published: September 25, 1973
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The theoretical equations for the membrane potential and the membrane permeability coefficient were derived on the basis of nonequilibrium thermodynamics. In this experiment, the system was constructed with two-cell chambers divided with a membrane and filled with solution of the same electrolyte but of different concentration. The Visking Cellotube was used as the membrane and the membrane potential and the membrane permeability coefficient were measured. The experimental temperature was 34°, and solutions of NaCl, KCl, LiCl, NH
4Cl, and CaCl
2 were used. By changing the concentration, the experimental membrane potential was in agreement with the theoretical values in a high concentration range. Also, charge density of the membrane was determined from the membrane potential and from the membrane permeability. These two values were in good agreement. Then P
*, defined as the concentration gradient in the membrane, was calculated. The value of P
* did not depend on the concentration of solution as much as did the membrane permeability coefficient P.
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YASUO MIYAKE, AISHIN SHINODA, MASAHARU FURUKAWA, CHIKAE SADAKATA, SHOJ ...
1973 Volume 93 Issue 9 Pages
1112-1115
Published: September 25, 1973
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Effect of calcium stearate content on the compacting phenomenon of pharmaceutical powders in the course of mixing with calcium stearate was examined. Changes in apparent density of the powders were not only influenced by calcium stearate content, but they varied with cumulative revolution number of the V-type mixer under all calcium stearate content. The patterns of these changes were similar among the same kind of powders, even if particle size was different. The most effective content of calcium stearate to specific surface area of powders from the view-point of increasing apparent density of pharmaceutical powders was considered to be constant for each pharmaceutic.
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TETSUJI KAMETANI, KIYOSATO NYU, SHIGEO IKEDA, TOMOHIRO TOMINAGA, RIICH ...
1973 Volume 93 Issue 9 Pages
1116-1119
Published: September 25, 1973
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Several 10-acyloxyprotoberberine derivatives (IXa-f), which were expected as hypotensives, were synthesized by acylation of 2, 3, 11-trimethoxy-5, 6, 13, 13a-tetrahydro-8H-dibenzo [a, g] quinolizine (VIII) with acetic anhydride and acid ch1oride.
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TETSUJI KAMETANI, KIYOSATO NYU, SHIGEO IKEDA, TOMOHIRO TOMINAGA, RIICH ...
1973 Volume 93 Issue 9 Pages
1120-1126
Published: September 25, 1973
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When O-demethylxylopinine (XIII) was synthesized from 1-(3-hydroxy-4-methoxybenzyl)-6, 7-dimethoxy-1, 2, 3, 4-tetrahydroisoquinoline (XI), 11-hydroxy-9-hydroxymethyl-2, 3, 10-trimethoxy-5, 6, 13, 13a-tetrahydro-8H-dibenzo [a, g] quinolizine (XIV) was also formed. Accordingly, in order to prevent formation of this by-product, 11-benzyloxy-2, 3, 10-trimethoxy-5, 6, 13, 13a-tetrahydro-8H-dibenzo [a, g] quinolizine (XII), which was synthesized by the Eschweiler-Clarke reaction of 1-(3-benzyloxy-4-methoxybenzyl)-6, 7-dimethoxy-1, 2, 3, 4-tetrahydroisoquinoline (X), was debenzylated to give XIII in a good yield. On the other hand, several 11-acyloxyprotoberberine derivatives. (XVIIa-f), which were expected as hypotensives, were synthesized by acylation of XIII with acetic anhydride and acid chloride. Optical resolution of (±)-xylopinine was carried out from which optically active xylopinine was obtained.
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AKIYO SAKUSHIMA, SUEO HISADA, SANSEI NISHIBE, ISAO INAGAKI
1973 Volume 93 Issue 9 Pages
1127-1130
Published: September 25, 1973
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After treating the methanol extractive of the leaves of Trachelospermum asiaticum NAKAI var.intermedium NAKAI with ethyl acetate, the mother liquor was extracted with butanol. Three flavone diglycosides (VIII, IX, and X) were isolated from butanol extract by column chromatography over silica gel. VIII and X were respectively identified with the authentic rhoifolin and luteolin 7-neohesperidoside (veronicastroside) in all respects. IX is a new compound, which was elucidated as apigenin 7-gentiobioside.
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SHUN'ICHI TSUKIYAMA, AKIRA TAKAMURA, MASAKO NAKANO
1973 Volume 93 Issue 9 Pages
1131-1137
Published: September 25, 1973
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This report deals with the effect of preagitation condition on emulsifying process with colloid mill. The apparatus consists of a cylindrical vessel (d=150 mm), Rushton-type impeller (d=49 mm), and an SL-type Asahi Homogenizer. Water and a mixture of n-C
7H
16 and CCl
4 were used as the continuous phase and dispersed phase, and Tween-20 was used as emulsifying agent. After continuous agitation for 6, 20, and 60 min at the revolution of 200, 330, 400, 530, and 660 rpm, the dispersed liquid was emulsified smaller in a colloid mill. The photographs of droplets were taken by a microscopic method. The particle size distribution was calculated and the following results were obtained. 1) Particle size distribution showed a logarithmic normal distribution in the colloid mill method. 2) With the increase of surface area on agitation process, energy efficiency of colloid mill, ηM, had a larger value. 3) Effect of preagitation was important in the colloid mill method. Summing up all experimental conditions, the optimum condition of preagitation was the revolution of 660 rpm and agitation time of 60 min.
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AKIYOSHI YOSHIDA, MINORU MORITA, SHUNTARO OGAWA
1973 Volume 93 Issue 9 Pages
1138-1143
Published: September 25, 1973
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Configurational analyses for the diastereoisomers of 1-chloro-3-(2-methylpiperidino)-1-phenylpropane (3α, 3β), alkyl or aryl 3-(2-methylpiperidino)-1-phenylpropyl ethers (C), and their quaternary bases (D) were carried out by measuring their nuclear magnetic resonance spectra. Each of amino chlorides (3α, 3β) and aminoethers (C) was found to be a single diastereoisomer. Quaternisation was found to introduce an axial methyl group into nitrogen of the piperidine ring.
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AKIYOSHI YOSHIDA, MINORU MORITA, SHUNTARO OGAWA
1973 Volume 93 Issue 9 Pages
1144-1153
Published: September 25, 1973
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Various methyl substituted phenyl 1-phenyl-3-piperidinopropyl ethers were synthesized, and their anticholinergic and mydriatic activities were examined. Phenyl 1-phenyl-3-piperidinobutyl ether methiodide (29), erythro-2-chlorophenyl 2-methyl-1-phenyl-3-piperidinopropyl ether methiodide (48), and 4-tolyl 3-piperidino-1-(3-tolyl) propyl ether methiodide (20) showed potent anticholinergic activities among these synthesized compounds.
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AKIYOSHI YOSHIDA, MINORU MORITA, SHUNTARO OGAWA
1973 Volume 93 Issue 9 Pages
1154-1161
Published: September 25, 1973
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Configurational analyses for diastereoisomers of 3-dimethylamino-2-methyl-1-phenylpropyl phenyl ether (1a), 2-methyl-1-phenyl-3-piperidinopropyl phenyl ether (1b), 2-methyl-3-(2-methylpiperidino)-1-phenylpropyl phenyl ether (1c), and their quaternary bases were made by their nuclear magnetic resonance spectra. It was found that the chemical shifts of H
(1) in the erythro-isomers appeared at a lower field and their coupling constants, JH
(1)H
(2), were smaller than those of the corresponding threo-isomers. The threo-amino chlorides were obtained from the erythro-amino alcohols with inversion, while erythro-amino chlorides were obtained together with threo-amino chlorides from the threo-amino alcohols. These configurational arrangements were retained in the ether condensation reactions.
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TETSUJI KAMETANI, KAZUO KIGASAWA, MINEHARU HIIRAGI, NAGATOSHI WAGATSUM ...
1973 Volume 93 Issue 9 Pages
1162-1164
Published: September 25, 1973
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Synthesis of 2-ethoxycarbonylmethyl-2-(3-substituted phenyl) cyclohexanone was examined by condensation of 2-(3-substituted phenyl) cyclohexanone with ethyl α-haloacetate in the presence of sodium amide or sodium hydride, and it was found that not only the expected alkylation but also the Darzens condensation took place in this reaction. The yield of alkylation decreased in the order of ethyl iodoacetate, bromoacetate, and chloroacetate.
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SHIN-ICHIRO SAKAI, AKINORI KUBO, KIYOAKI KATANO, NOBUO SHINMA, KUMIKO ...
1973 Volume 93 Issue 9 Pages
1165-1182
Published: September 25, 1973
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From the cyanogen bromide reaction of yohimbine (I) in ethanol-chloroform, 3R-ethoxy-3, 4-seco-cyanamide (II) had been obtained by Albright and Goldmann,
6 but it was found that the ratio of reaction products (R and S) depends on the molar ratio of ethanol to the substrate (Table I). Stereospecific ring closing reaction of IIIa and IIIb with hot acetic acid was found to yield I(=IVa) and pseudoyohimbine (IVb), respectively. A similar result was obtained for hirsutine (VI), which gave 3R- and 3S-ethoxy-3, 4-seco-cyanamide (VIIa and b). Both compounds underwent stereospecific ring closure to dihydrocorynantheine (VIIIa) and VI (=VIIIb), respectively. Treatment of gardnerine (XII) with BrCN resulted in the formation of its cyanamide ether (XIII). In the ring closing reaction with hot acetic acid, XIII gave a new iminoindolenine derivative (XIV). Two convenient routes are described for the syntheses of vobasine-type alkaloids from gardnerine acetate (XXVI). When phenyl chloroformate was used instead of BrCN, in a two-phase reaction with aqueous alkali and pure chloroform, N
a-methylgardnerine acetate (XXVII) directly provided an amorphous 3-hydroxy-3, 4-seco-urethane derivative (XXVIII) in 60-70% yield. XXVIII was converted to the desired 2-acylindole alkaloid (XXIX), mp 197 -199°, in two steps. Treatment of XXVI with BrCN in 10% methanolpure chloroform resulted in the formation of 3-methoxy-3, 4-seco-cyanamide (XXXIV). Oxidation of XXXIV with t-BuOCl gave 3-keto-3, 4-seco-cyanamide (XXXV) in 39% yield. XXXV was converted to the desired 2-acylindole alkaloid (XXXIX), mp 206.5-209°, in two steps.
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KOUICHI YOSHIOKA, GIICHI GOTO, KENTARO HIRAGA
1973 Volume 93 Issue 9 Pages
1183-1187
Published: September 25, 1973
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Reaction of γ-ketoamyl alcohol with diethyl oxalate in the presence of sodium ethoxide gave ethyl 5, 6-dihydro-4, 8-dioxo-4H, 8H-pyrano [3, 4-b] pyran-2-carboxylate (IV). Treatment of the other γ-keto alcohols (I, II, III) with diethyl oxalate in the presence of a base afforded dihydropyrones (IX, X, XI). Reaction of IV with primary amines yielded pyridone derivatives.
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EUN BANG LEE
1973 Volume 93 Issue 9 Pages
1188-1194
Published: September 25, 1973
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The present study was undertaken to compare the pharmacological activities of crude platycodin reported previously with the clinical uses of platycodi radix in the oriental medicine. Crude platycodin shows marked antiulcerative, anti-inflammatory, hypotensive, and expectorant actions, and moderate analgesic, antipyretic, antitussive, and anticholinergic activities. Sedative, antihistaminic, and antiallergic actions were also exhibited. On the other hand, the clinical uses of platycodi radix that are inferred from 23 kinds of prescriptions used frequently in the oriental medicine are as follows. Fifty-six percent of the indications for anti-inflammation, 10.6% for expectoration, 9.7% for analgesia, 8.0% for antipyresis, 4.4% for hypotension, and 3.5% for antitussive, It was used even rarely for sedation, antiulceration, antigastritis, and antiallergy. It may be concluded that the clinical uses of platycodi radix are quite parallel with the pharmacological activities of crude platycodin, and the clinical application of the radix may be attributed approximately to the effect of crude platycodin. Furthermore, it is suggested that the radix may be also used for the control of peptic ulcer.
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MASAYUKI NAKAGAKI, YOH SANO
1973 Volume 93 Issue 9 Pages
1195-1200
Published: September 25, 1973
Released on J-STAGE: May 30, 2008
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Viscosity measurements were carried out for the mixed solutions of bovine serum albumin and chondroitin sulfate of various mixing ratios in 0.01M sodium chloride solutions at 25°. Since the soluble complex was formed in this system, the intrinsic viscosity of the complex molecule [η]
m was calculated from the apparent intrinsic viscosity [η]
t which had been obtained experimentally by assuming that the solutions contained one solute whose concentration was the sum of the two solutea. The values of [η]
m thus obtained were compared with theoretical values of the intrinsic viscosity calculated for various models from the three quantities of the complex molecule, M
m, V
m, and R
gm, obtained by the light scattering studies as reported in the previous paper. It was concluded from these results that the prolate spheroid is the most suitable model for the complex molecules.
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TOZABURO KURIHARA, MASAO KIKUCHI
1973 Volume 93 Issue 9 Pages
1201-1205
Published: September 25, 1973
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From the steam distillate of the ether extract of flower of Pueraria thunbergiana, nine kinds of alcohol and four kinds of acid were isolated as the fragrant compositions. Irisolidone, genistein, daidzein, quercetin, p-coumaric acid, and some paraffins were also identified in the residue of the steam distillation.
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YORISHIGE IMAMURA, HISASHI ICHIBAGASE
1973 Volume 93 Issue 9 Pages
1206-1210
Published: September 25, 1973
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The inhibitory effect of non-steroidal anti-inflammatory agents on the binding of sulfadimethoxine (SDM) with bovine serum albumin (BSA) in vitro was determined by equilibrium dialysis method. The effect of non-steroidal anti-inflammatory agents on antibacterial activity of SDM in the presence of BSA was analyzed by thin-layer paper disc method and compared with the results obtained from the former. The effect of sulfadimethoxine N
4-acetate, which is one metabolite of SDM, on the binding of SDM with BSA, and antibacterial activity of SDM in the presence of BSA was tested by the same method. These studies revealed the following : (1) The displacing activity of non-steroidal anti-inflammatory agents on the binding of SDM with BSA decreased in the order of phenylbutazone, salicylic acid, mefenamic acid, bucolome, indomethacin, and benzydamine. (2) Antibacterial activity of SDM was markedly reduced by the addition of BSA. (3) Antibacterial activity of SDM that decreased in the presence of BSA was recovered by the addition of non-steroidal anti-inflammatory agents. This activity decreased in the order of phenylbutazone, salicylic acid, bucolome, indomethacin, and benzydamine. (4) Sulfadimethoxine N
4-acetate also inhibited the binding of SDM with BSA and increased this reduced antibacterial activity of SDM.
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KAZUO ITO, HIROSHI FURUKAWA, HITOSHI TANAKA
1973 Volume 93 Issue 9 Pages
1211-1214
Published: September 25, 1973
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The alkaloidal components of the leaves of Erythrina X bidwilli LINDL. (Leguminosae) were examined. The known erythrina alkaloids, erythraline (II) and erysodine (III), and the known benzylisoquinoline alkaloid, N-nororientaline (V), were isolated. Two new alkaloids which were named erythrinine (I) and erybidine (VII) were also isolated and characterized.
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KAZUO ITO, HIROSHI FURUKAWA, HITOSHI TANAKA
1973 Volume 93 Issue 9 Pages
1215-1217
Published: September 25, 1973
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Erythrinine (mp 197-200°) has been isolated from the leaves of Erythrina X bidwilli LINDL. (Leguminosae). Chemical and spectroscopic investigations have shown that erythrinine has the stereostructure shown by formula TV.
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KAZUO ITO, HIROSHI FURUKAWA, HITOSHI TANAKA, THUNSHU RAI
1973 Volume 93 Issue 9 Pages
1218-1221
Published: September 25, 1973
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Erybidine (mp 178-180°) is a new alkaloid which has been isolated from the leaves of Erythrina X bidwilli LINDL. (Leguminosae) along with three known Erythrina alkaloids, erythraline (I), erysodine (II), and erythrinine (IV). O-Methylerybidine was proved to be identical with 2, 3, 11, 12-tetramethoxydibenz [d, f] azonine (VI), which was derived from erysodienone (IX). The structure of erybidine (V) was established by the synthesis of this alkaloid from erysodienol (XII). From the viewpoint of biosynthesis, it is interesting that the presence of the dibenz-[d, f] azonine-type base, which was postulated as one of the intermediates of Erythrina alkaloids biosynthesis, was proved, in addition to some erythrinan-type bases.
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ISAO ISHIGURO, TAKEYUKI IKENO, HIROMU MATSUBARA
1973 Volume 93 Issue 9 Pages
1222-1230
Published: September 25, 1973
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Changes in the chemical constituents in four kinds of bees were examined in the three stages of larva, pupa, and imago. Protein content in larva stage of Vespa lewisi was the highest compared to other three species. Many soluble protein bands in the stage of pupa were separated by disc electrophoresis. In imago stage, new protein bands which were not observed at larva and pupa stages appeared. Nonprotein-nitrogen content in V.lewisi and V.xanthoptera increased markedly at imago stage but there was no change in other two bees. Larva and pupa of four kinds of bees contained glutamic acid in a high concentration. Vitamin A content in the bees decreased with progressive development. Thiamine in the larva and imago stages was found mainly in the body in an esterified form. Riboflavin in the bees was mostly FAD. Total ascorbic acid was 35 mg% and half of them was in a reduced form. Bees contained sodium, potassium, and phosphorus in a high concentration and the ratio of sodium and potassium varied throughout their development but phosphorus was constant at each stage.
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ISAO INAGAKI, SUEO HISADA, SANSEI NISHIBE, AKIYO SAKUSHIMA
1973 Volume 93 Issue 9 Pages
1231-1234
Published: September 25, 1973
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The methanol extract of the leaves of Trachelospermum asiaticum NAKAI var.intermedium NAKAI was treated (Chart 1) and from the ethyl acetate-soluble fraction, succinic acid, apigenin, luteolin, arctigenin, apigenin 7-glucoside, luteolin 7-glucoside, and luteolin 4'-glucoside were isolated and identified respectively with authentic samples.
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TAKEO HIGASHINO, TETSUJI WASHIZU, EISAKU HAYASHI
1973 Volume 93 Issue 9 Pages
1234-1235
Published: September 25, 1973
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α-Haloesters reat with carbonyl compounds like aldehydes, ketones, and esters, in the presence of zinc, to form β-hydroxy esters, the so-called Reformatsky reaction, which was said to be limited to the foregoing carbonyl compounds. In the present series of work, quinazoline was taken up in place of carbonyl compounds and the Reformatsky reaction of quinazoline with ethoxycarbonylmethylzinc bromide was carried out. The reaction progressed and ethyl 4-quinazolioeacetate was formed, though in a low yield, and formation route of this compound was considered.
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TAMIO NISHIMURA, SHIN YOSHII, HIROSHIGE TOKU, HITOMI MOCHIZUKI
1973 Volume 93 Issue 9 Pages
1236-1242
Published: September 25, 1973
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The relationship between the chemical structure and antibacterial activity of alkoxybenzalacetone amidinohydrazones was studied. These compounds showed a maximum antibacterial activity with the 4-6 carbon atoms in the alkoxyl group. The position of alkoxyl group and substitution of H in the α-position with CH
3 in benzalacetone moiety have no effect on the antibacterial activity. On the substitution of amidino moiety, the antibacterial potency generally decreased in the order of -NH
2, -[chemical formula], and -[chemical formula]. The activities of these compounds against gram-positive bacteria, gram-negative bacteria and fungi decreased in this order.
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TAMIO NISHIMURA, HIROSHIGE TOKU, SHIN YOSHII, MITSUE MORISHIGE
1973 Volume 93 Issue 9 Pages
1242-1246
Published: September 25, 1973
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The relationship between the chemical structure and antibacterial activity of alkoxyacetophenone amidinohydrazones was studied. m- or p-Alkoxy compounds showed maximum antibacterial activities with carbon atoms in the alkoxy group, and o-alkoxy compounds with 8-10 carbon atoms. Substitution of -NH
2 with -[chemical formula], -[chemical formula] or -[chemical formula] in amidino moiety generally lowered the activity. Antibacterial potency of these compounds against gram-positive bacteria (G+), gram-negative bacteria (G-), and fungi. (F) decreased in this order but compounds having -[chemical formula] or -[chemical formula] at amidino moiety showed the order of G+>F>G-.
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TAMIO NISHIMURA, SHIN YOSHII, HIROSHIGE TOKU, MITSURU WATANABE
1973 Volume 93 Issue 9 Pages
1247-1250
Published: September 25, 1973
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The relationship between the chemical structure and antibacterial activity of amidino-hydrazones of alkoxybenzaldehydes and alkoqcinnamaldehydes was studied. Although there were a few exception, o-alkoxybenzaldehyde amidinohydrazones showed maximum antibacterial activity with a carbon number of 10, m- or p-alkoxybenzaldehyde amidino-hydrazones with a carbon number of 6 and p-alkoxycinnamaldehyde amidinohydrazones with a carbon number of 5. Antibacterial potency of alkoxybenzaldehyde unsubstituted amidinohydrazones fell in the order of para, meta and ortho. Substitution of -NH
2 with [chemical formula] of amidino moiety in o-alkoxybenzaldehyde amidinohydrazones increased the antibacterial potency against gram-positive bacteria and fungi.
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HIDEJI ITOKAWA, YASUO AKITA, MIKIO YAMAZAKI
1973 Volume 93 Issue 9 Pages
1251-1252
Published: September 25, 1973
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