Chemical and Pharmaceutical Bulletin

Studies on Pyrimidine Derivatives and Related Compounds. XLIV. Syntheses of Thiazolo [3, 2-a] pyrimidine Derivatives

Akira Takamizawa, Kentaro Hirai, Teruyuki Ishiba, Yoshihiro Matsumoto

1967 Volume 15 Issue 6 Pages 731-739
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.731

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Ethyl 2-thio-1, 2, 3, 4-tetrahydropyrimidine-5-carboxylate (VIII) and 2-thio-1, 2, 3, 4-tetrahydropyrimidine-5-carbonitrile (XXIII) were used for various kinds of condensation reactions. From the reaction with ethylene dibromide, VIII gave biscompound IX, and with phenacyl-bromide and p-chlorophenacylbromide thiazolo [3, 2-a] pyrimidine derivatives were obtained. In this reaction, 5H-thiazolo [3, 2-a] pyrimidine derivative (XIII, XVII, XXV) and the 7H-isomer (XIV, XVIII, XXVI) were obtained separately. The structures of these isomers were assigned from NMR and UV spectra. In this thiazolo [3, 2-a] pyrimidine syntheses, 3-hydroxy compounds (XII, XVI, XXIV) were considered to be the key intermediates.

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Mass Transfer with Chemical Reaction Longitudinal Dispersion in Two-Phase Continuous-Flow Operations. I.

Yoshiharu Miura

1967 Volume 15 Issue 6 Pages 740-751
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.740

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The evaluations of the concentration distributions necessary for predicting the extents of chemical reaction and mass transfer and the length of the apparatus required for obtaining the desired completions of the chemical reaction and mass transfer are permitted by a general theoretical treatment, taken into consideration the effect of longitudinal dispersion of both fluids for two-phase continuous-flow systems accompanying general second order chemical reaction, mass transfer and longitudinal dispersion. The general solutions for the concentration distributions were numerically obtained by a digital computer. The effects of stage number in the finite difference equation, chemical reaction rate and residence time on the concentration distribution were shown by numerical calculations through Equations (11) to (13). The influence of chemical reaction rate on the concentration distribution is less as the resistance to mass transfer in phase with chemical reaction is less than that in the other phase without chemical reaction and for example, the reaction rate or the mass transfer rate in the phase with chemical reaction is higher. The concentration distribution can be estimated analytically in the case where the resistance to mass transfer in the phase without chemical reaction is controlling or the degree of longitudinal dispersion is very high.

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Stereoselective Hydrogenation of o-, m-, and p-Xylenes by Transition Metal Catalysts of Group VIII

Haruhiko Yamamoto, Kunio Noda, Hiroyuki Horiguti, Takao Kwan

1967 Volume 15 Issue 6 Pages 752-755
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.752

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The stereoselective hydrogenation of three xylene isomers to yield cis- and trans-dimethylcyclohexane has been investigated on eight kinds of transition metal catalysts by the gas chromatographic pulse technique. The selectivity for the formation of trans-dimethylcyclohexane was found to be of the following sequence with respect to the hydrogenation of o-, m- and p-xylene. [chemicalformula] It was pointed out that the selectivity sequence parallels with the ability of the transition metals to form π-allylic complexes in the case of the hydrogenation of o- and p-xylene and that the remarkable suppression of transformation, as found in the case of m-xylene, is due to the steric hindrance rather than the poor ability of the transition metals to form an adsorbed π-allylic adsorbed intermediate on the surface.

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The X-ray Analysis of Lenthionine, an Odorous Substance of Shiitake, an Edible Mushroom

Masao Nishikawa, Kazuhide Kamiya, Shigeru Kobayashi, Katsura Morita, Y ...

1967 Volume 15 Issue 6 Pages 756-760
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.756

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The chemical and stereochemical structure of lenthionine has been established by the X-ray method. Lenthionine crystallizes in the monoclinic system, space group P2₁/a-C⁵_2h, with four molecules of S₅ (CH₂)₂ in the unit cell. Using a three-dimensional Patterson function and minimum functions, all atomic positions were determined. The least squares method was adopted to distinguish CH₂ groups from sulfur by the temperature factors. Thus the three-dimensional molecular geometry has been elucidated to be in a chair form, having C₂ pseudo-symmetry.

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Studies on Diazabenzobicyclo [3.3.1] nonane System. VII. Synthesis of 1, 2, 3, 4, 5, 6-Hexahydro-1, 5-methanobenzo [e][1, 2] diazocine Derivatives and an Example of Abnormal Cleavage of Hydrazide by Lithium Aluminum Hydride

Shunsaku Shiotani, Kemmotsu Mitsuhashi

1967 Volume 15 Issue 6 Pages 761-767
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.761

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3-Oxo-1, 2, 3, 4-tetrahydro-1-naphthoic acid obtained by reduction of 3-methoxy-1-naphthoic acid with sodium amalgam was condensed with N-methyl-N-acetylhydrazine to give the corresponding hydrazone (VIII). VIII was submitted to catalytic reduction over Adams catalyst, methylation with formic acid-formalin, hydrolysis with hydrochloric acid, esterification with methanol and intramolecular cyclization to afford 3, 4-dimethyl-3, 4, 5, 6-tetrahydro-1, 5-methanobenzo [e][1, 2] diazocin-2(1H)-one(XII). Treatment of XII with lithium aluminum hydride gave an abnormally cleft product, 4-methyl-5, 6-dihydro-1H, 4H-1.5-methanobenzo [e][1, 2] diazocine (XVII). XVII was reduced with lithium aluminum hydrode to give 4-methyl-1, 2, 3, 4, 5, 6-hexahydro-1, 5-methanobenzo-[e][1, 2] diazocine (XVIII). Structures of XII, XVII and XVIII were confirmed by chemical as well as spectral methods.

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The Structure of Stenine, a New Alkaloid Occurring in Stemona Tuberosa

Shojiro Uyeo, Hiroshi Irie, Hiroshi Harada

1967 Volume 15 Issue 6 Pages 768-770
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.768

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A new alkaloid, stenine, has been isolated from the roots of Stemona tuberosa and its structure established as represented by formula II.

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Fatty Acid Components of Lipid Fractions of Yoshida Sarcoma and Rat Ascites Hepatomas

Yoshio Sakurai, Takao Iwaguchi

1967 Volume 15 Issue 6 Pages 771-773
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.771

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Lipid content of the ascites tumors and host liver differed much from each other. The ratios of saturated acids to the unsaturated in the neutral lipid fraction of the tumors and the liver were always less than 1. On the contrary, the similar ratios in the phospholipid fraction of the tumors were more than 1 without exception, while that of the liver were less than 1 as in the case of neutral lipid fraction.

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Reaction of Amide Homologs. XVIII. Catalytic Hydrogenation of N-Arylmethylene-1-acylamino-1-arylmethylamines and Hydroamides in the Presence of Formamide and Related Studies

Minoru Sekiya, Akira Hara, Keiichi Ito, Jiro Suzuki, Kozo Tanaka

1967 Volume 15 Issue 6 Pages 774-785
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.774

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Catalytic hydrogenations of both series of the compounds, N-arylmethylene-1-acylamino-1-arylmethylamines and hydroamides, over Raney nickel catalyst were examined under both conditions, in the presence of formamide and in the absence of it. While under the latter condition either of the hydrogenations proceeded to give secondary amine at least as one of the principal reduction products, under the former condition resulted in the predominant formation of N-formylated priomary amine. In correlation with the previously reported azomethine-formamide hydrogenation the reaction paths for the hydrogenations influenced by formamide were revealed to be of involving intermediates, azomethine, aldimine, and N-arylmethylene-1-formamido-1-arylmethylamine (in the case with hydroamides).

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Structure of Catalpalactone, a New Phthalide from Catalpa Wood

Hiroyuki Inouye, Takuo Okuda, Yasubumi Hirata, Naotaka Nagakura, Masao ...

1967 Volume 15 Issue 6 Pages 786-792
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.786

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Catalpalactone, C₁₅H₁₄O₄, a new type of phthalide derivative has been isolated from the wood of Catalpa ovata G.DON and C.bignonioides WALT, and its structure has been determined to be represented by the formula (I).

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Ableitung von 9-Methyl-1, 2, 3, 4, 6, 7, 12, 12b-octahydroindolo [2, 3-a]-chinolizin aus 6-Methylchinolin

Makoto Takahashi, Ryosuke Tanabe

1967 Volume 15 Issue 6 Pages 793-796
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.793

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In Fortsetzung der Versuche ^{1, 2)}zur Ableitung von Derivaten des Octahydroindolochinolizins aus dem entsprechenden Chinolin haben wir trans-9-Methyl-1, 2, 3, 4, 6, 7, 12, 12b-octahydroindolo [2, 3-a]chinolizin (VIII) aus 4-Chlor-6-methylchinolin-1-oxyd hergestellt.

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Osmium Tetroxide Oxidation of Hopa-15, 17(21)-diene, Dehydrozeorinin, and Hop-17(21)-ene

Yoshisuke Tsuda, Kimiaki Isobe

1967 Volume 15 Issue 6 Pages 797-801
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.797

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The structures of the diol and the conjugated ketone obtained from the osmium tetroxide oxidation of hopa-15, 17(21)-dienes (I) were now revised and correctly assigned as IV and V, respectively, the former being obtained by lithium aluminum hydride decomposition and the latter by hydrogen sulfide decomposition of the intermediate osmate. Hop-17(21)-ene (VI) was also found to give the seco-diketone (VIII) in lesser yield. A probable mechanism for the formation of the seco-diketones was also discussed.

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Reaction of Amide Homologs. XIX. Thermal Reactions of Azomethines with Formates and Formamide

Minoru Sekiya, Keiichi Ito, Akira Hara, Jiro Suzuki

1967 Volume 15 Issue 6 Pages 802-815
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.802

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Thermal reactions of the representative azomethines of N-benzylidene type with the reagents, trimethylammonium formate given by 5HCO_-2H·2N (CH₃)₃, ammonium formate and formamide, were examined in order to elucidate distinctions among them. The reduction and oxidation coureses as to the formate reaction and the formamide reaction were definitely distinguished from each other ; in the former reaction saturation of the azomethine double bond is induced by ixidation of formic acid to carbon dioxide and in the latter reaction reductive cleavage at the double bond, induced by self-oxidation of the azomethine, leads to the formation of the cleaved N-formylated primary amines. Elucidation on the mechanistic paths as to both of the essential reactions was investigated. Particularly, the pathways of the very complicated formamide reaction were declared to be of involving aldimine, hydroamide, N-arylmethylene-1-formamido-1-arylmethylamine and N, N'-arylmethylenebisformamide as major or minor intermediates.

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Studies on Pyrimidine Derivatives and Related Compounds. XLV. On Some Synthetic Methods of N-[1-(2-Oxo-1, 3-oxathian-4-ylidene) ethyl]-N-[(2-methyl-4-amino-5-pyrimidinyl)-methyl] formamide

Akira Takamizawa, Kentaro Hirai, Yoshio Hamashima, Hisako Ito

1967 Volume 15 Issue 6 Pages 816-821
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.816

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The reaction of phosgene with thiamine chloride (IIa) or nitrate (IIb) gave O-chlorocar-bonylthiamine (IX) in good yield. Treatment of IX with alkali afforded N-[1-(2-oxo-1, 3-oxathian-4-ylidene) ethyl]-N-[(2-methyl-4-amino-5-pyrimidinyl) methyl] formamide (XIII). The reaction of thiamine sodium salt (III) with aryloxycarbonyl chloride (phenoxy-, p-methyl-phenoxy, p-methoxyphenoxy) gave corresponding S-aryloxycarbonylthiamine (XIIa∼c), and further treatment of XIIa∼c with alkali afforded XIII in good yield. On the other hand, IX reacted with sodium salts of phenol, p-cresol, and p-methoxyphenol to give corresponding O-aryloxycarbonylthiamine (XIa∼c). Treatment of XIa∼c with alkali also gave XIII in low yield. Therefore, it was assumed that XI and XII gave XIII in independent way by alkali treatment.

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A Synthesis of Dibenzo (a, h) quinolizidine System by way of Immonium Salt Intermediate

Yuichi Kanaoka, Miwako Ochiai, Yoshio Ban

1967 Volume 15 Issue 6 Pages 822-825
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.822

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A mixture of 3, 4-dihydroisoquinoline derivative and 3, 4-dimethoxyphenethyl bromide afforded dibenzo (a, h) quinolizidine derivative in one step by heating. This cyclization was interpreted in terms of electrophilic reactivity of immonium salt intermediate.

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Studies on Hydrogen Exchange. V. Electrophilic Deuteration of Quinoline and Its 1-Oxide

Yutaka Kawazoe, Masako Ohnishi

1967 Volume 15 Issue 6 Pages 826-832
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.826

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The reactivity toward acid-catalyzed deuterium substitution was compared with each other position of quinoline and its 1-oxide. Discussion was made in connection with other electrophilic reactivities in nitration and so on. Many selectively deuterated derivatives were synthesized on the course of the present study.

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Reaction of Amide Homologs. XX. Thermal Reaction of N, N'-Benzylidenebisamides with Formates and Formamide

Minoru Sekiya, Yukichi Harada, Kozo Tanaka

1967 Volume 15 Issue 6 Pages 833-839
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.833

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Thermal reactions of some representative N, N'-benzylidenebisamides with the reagents, trimethylammonium formate given by 5HCO₂H·2N (CH₃)₃, ammonium formate and formamide, were examined to see reaction nature and to elucidate distinctions among them. In the formate reaction reductive fission at the carbon-nitrogen bond of bisamide was mainly induced by oxidation of formic acid to carbon dioxide resulting in formation of the corresponding N-benzylamide and in the formamide reaction formation of N-benzylformamide was induced by self-oxidation of bisamide. Ammonium formate behaved in the reaction in a poition between formate and formamide.

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The Adrenergic Neurone Blocking Action of [2-(Methylphenylamino)-ethyl] guanidine Sulfate. II.

Hikaru Ozawa, Susumu Sato

1967 Volume 15 Issue 6 Pages 840-844
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.840

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[2-(Methylphenylamino) ethyl] guanidine sulfate (MPG) was found to be an effective antihypertensive agent during repeated administration at 10mg./kg. subcutaneously to conscious renal hypertensive rats. Prolonged reduction of contractions evoked by preganglionic stimulation of the cervical sympathetic nerve in the nictitating membrane of cat was observed following a single intravenous administration of 10mg./kg. of MPG. This procedure also caused the potentiation of norepinephrine-induced responses and suppression of tyramineor amphetamine-induced response in the nictitating membrane of the cat and blood pressure of the dog. In the experiment of intra-arterial administration, the postganglionic cervical sympathetic nerve blocking activity was observed to be one-half as potent as guanethidine in the nictitating membrane of cat. The hypotensive effect of MPG would be considered to be depletion of catecholamines and blockade of sympathetic transmission at adrenergic nerve level.

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Some Homolytic Reaction Behaviors of Diethyl Azodicarboxylate

Munemitsu Tomoeda, Saburo Kanahara, Mutsuko Urata, Junji Yoshizawa

1967 Volume 15 Issue 6 Pages 845-853
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.845

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Pyrolytic cleavage of the azo-bridge of diethyl azodicarboxylate (Ia) at 200∼210° was studied and was shown to give diethyl oxalate (VI), tetraethyl hydrazine-N₁, N₁, N₂, N₂-tetra-carboxylate (VIII), triethyl hydrazine-N₁, N₁, N₂-tricarboxylate (IX), diethyl hydrazine-N₁, N₂-dicarboxylate (X), and carbon dioxide, proving formation of the ethoxycarbonyl radical (III) as an important transitionally formed intermediate of the reaction. A homolytic mechanism with the diradical (IV) and ethoxycarbonyl radical (III) as intermediates was tentatively sug-gested for the reaction. Surprisingly, Ia, when treated with alumina or silica gel at room temperature, gave almost same pattern of products obtained by the pyrolysis, yielding VIII, IX, X and carbon dioxide. A photolysis of Ia on a tungsten lamp also gave IX, X, and carbon dioxide.

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Studies on Peptides. XIV. Synthesis of Lysyl-S-benzylcysteinylalanylglutaminyl-S-benzyl-cysteinylhistidine, a Peptide related to Horse Heart Cytochrome C.

Haruaki Yajima, Osamu Nishimura, Koichi Kawasaki, Yoshio Okada

1967 Volume 15 Issue 6 Pages 854-862
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.854

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A partially protected hexapeptide, lysyl-S-benzylcysteinylalanylglutaminyl-S-benzyl-cysteinylhistidine, related to the heme portion of horse heart cytochrome C was described. In addition, S-benzylcysteinylalanylglutaminyl-S-benzylcysteine, lysyl-S-benzylcysteinylalanylglutaminyl-S-benzylcysteine and some S-benzylcysteine peptides were prepared.

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Studies in the Indole Series. II. A General Synthesis of Cycloalkan[b]indolones

Kikuo Ishizumi, Takayuki Shioiri, Shun-ichi Yamada

1967 Volume 15 Issue 6 Pages 863-872
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.863

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A general synthesis of cycloalkan[b]indolones from 3-indolealkanoic acids is described. Effect of 1-alkyl substitution of indole was observed on the ultraviolet spectra of 1-methyl-3-indolealkanoic acids. Cyclization of 3-indolealkanoic acids was mostly effected with polyphosphoric acid. Ring closure of Vc and Vd with PPA brought about concomitant expected monomers (VIIc and VIId) and dimers (VIIIa and VIIIb). The structure proof of the dimers was obtained from analytical and spectral data.

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Studies on the Molecular Compounds of Organic Medicinals. IV. Physico-pharmaceutical Properties of the Molecular Compound of Homosulfanilamide and Sulfathiazole

Keiji Sekiguchi, Eiji Owada, Keiji Ito

1967 Volume 15 Issue 6 Pages 873-878
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.873

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In order to obtain wider knowledges on the physico-pharmaceutical properties of the molecular compounds of organic medicinals, the dissolution behaviors, solubility equilibrium and the nature of the bonding between components were investigated with the compound of homosulfanilamide and sulfathiazole. When the molecular compound was dissolved, the stable equilibrium, not the metastable one was rapidly attained. On the contrary, much differences in dissolution behaviors were observed with the corresponding physical mixture and the equilibrium was not reached even after 24 hours due to deposition of the compound on sulfathiazole particles. From the phase diagram constructed, it was confirmed that the system belongs to the type where the formed compound is not decomposed by water. By applying the solubility product principle, formation constants at various temperatures were obtained and the changes of enthalpy, free energy and entropy for the molecular compound formation in solutionwere calculated. It was supposed from these thermodynamic constants and the data of IR and electric conductance measurements that in the compound, the bonding between homosulfanilamide and sulfathiazole is caused by ionic interaction.

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Studies on the Syntheses of Heterocyclic Compounds. CLXXXII. A Modified Synthesis of So-called Corpaverine

Tetsuji Kametani, Toyohiko Kikuchi

1967 Volume 15 Issue 6 Pages 879-883
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.879

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Bischler-Napieralski cyclization of the phenethylamide (VII) having a benzyloxyl group in the 3-position of the benzene ring was found to take place in the position para and ortho to the benzyloxyl group, but both isoquinoline derivatives could not be separated in the stage of 3, 4-dihydroisoquinolines (VIIIa and VIIIb), its methiodides (IXa and IXb), and 1, 2, 3, 4-tetrahydroisoquinolines (Xa and Xb), even if various procedures as thin-layer chromatography were examined. Accordingly, after Xa and Xb had been hydrolysed, attempt to separate both compounds (I and XI) by thin-layer chromatography was successfully carried out. After all, so-called corpaverine (I), namely, 8-hydroxy-6, 7-dimethoxy-1, 2, 3, 4-tetrahydro-1-(4-methoxybenzyl)-2-methylisoquinoline, was obtained besides its isomer (XI) in a comparatively better yield than that of our previous method. Furthermore, selective methylation of XIII with diazomethane also gave both compounds (I and XI), which were characterized as perchlorate and oxalate, respectively.

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Investigations on Pantothenic Acid and Its Related Compounds. VIII. Biochemical Studies. (3). Growth Response of Lactobacillus arabinosus 17-5 to D-Pantothenic Acid 4'-Phosphate

Yasushi Abiko, Masao Shimizu

1967 Volume 15 Issue 6 Pages 884-886
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.884

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The Polyphosphoric Acid-Catalyzed Ring Opening of 4, 5-Epoxy-3-oxo Steroids. IV. The Synthesis of 17α-Hydroxy-4-ethylthiopregn-4-ene-3, 20-dione and Its Analogs

Munemitsu Tomoeda, Akihiko Ishida, Toshitaka Koga

1967 Volume 15 Issue 6 Pages 887-892
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.887

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An Improved Synthesis of Styphnic Acid

Tetsuji Kametani, Kunio Ogasawara

1967 Volume 15 Issue 6 Pages 893
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.893

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Selective Acylation of the Amino or the Primary Hydroxyl Group of Cytidine

Takuma Sasaki, Yoshihisa Mizuno

1967 Volume 15 Issue 6 Pages 894-896
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.894

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Gas Chromatography of Compounds in Vitamin B₆ Group

Toshio Imanari, Zenzo Tamura

1967 Volume 15 Issue 6 Pages 896-898
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.896

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Regulation of Nicotine Synthesis in Tobacco Callus Tissue

Tsutomu Furuya, Hisashi Kojima, Kunihiko Syono

1967 Volume 15 Issue 6 Pages 901-903
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.901

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New Constituents of Chamaecyparis formosensis MATSUM

Takashi Toda, Y.S. Cheng, Tetsuo Nozoe

1967 Volume 15 Issue 6 Pages 903-905
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.903

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Effect of N-Substituent on the Protein-Binding of Carcinogenic Aminoazo Dyes

Akira Hanaki

1967 Volume 15 Issue 6 Pages 906-908
Published: June 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.906

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