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Hideo Kano, Yasuo Makisumi
1958 Volume 6 Issue 6 Pages
583-586
Published: December 15, 1958
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A number of 5-substituted 7-methyl-s-triazolo [4, 3-α]-and-tetrazolo [1, 5-α] pyrimidines were prepared by nucleophilic displacement of the corresponding chloro compounds (VII and VIII). These compounds are being screened for antimetabolite and anticancer activity.
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Shigehiko Sugasawa, Tozo Fujii
1958 Volume 6 Issue 6 Pages
587-590
Published: December 15, 1958
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Tozo Fujii
1958 Volume 6 Issue 6 Pages
591-601
Published: December 15, 1958
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1-Benzyl-2-oxo-5-ethyl-4-piperidineacetic acid (III) was debenzylated by metallic sodium in liquid ammonia and the product was alkylated with 3, 4-dimethoxyphenethyl bromide to yield N-(3, 4-dimethoxyphenethyl)-lactam derivative (IX). The chloride of the latter was coupled with 3, 4-dimethoxyphenethylamine and the resultant oily amide (X) was cyclized to give dehydroemetine (XI), which was also obtained as a syrup. For characterization the latter was converted to the crystallizable dl-rubremetinium bromide (XII), the ultraviolet and infrared absorption spectra of which were respectively identical with those of the authentic sample of d-salt. Aiming at the total synthesis of emetine the stereochemical assignment of two forms (Va and b) of (V) was attempted, but so far was unsuccessful. [Added in proof] After this paper was submitted for publication, the communications of M. Barash and J.M. Osbond (Chem. & Ind. (London), 1958, 490) and of A. Brossi, A. Cohen, J.M. Osbond, Pl.A. Plattner, O. Schnider, and J.C. Wickens (ibid., 1958, 491) became available in our Library. The former authors describe the synthesis of emetine and its stereoisomers and the latter, stereochemistry of emetine.
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Shigehiko Sugasawa, Hisayuki Matsuo
1958 Volume 6 Issue 6 Pages
601-607
Published: December 15, 1958
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A modified Emde degradation, in which a combination of Raney nickel alloy and sodium hydroxide solution was used as the reduction agent in place of sodium amalgam in the original Emde reaction, was applied to four open-chain quaternary salts (I to IV) to give the corresponding des-N products and trimethylamine in a good yield as summarized in Table I. Degradation of cyclic bases, such as phenanthridine and its 6-methyl derivative, by this modified method also proceeded smoothly under the same conditions as above to form the corresponding des-N compounds (VIII and XIV) via dihydromethine bases (VI and XIII). So far as these experiments were concerned, the cleavage was effected usually with a better yield of the products and under milder working conditions than those of the original method.
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Shoji Shibata, Shinsaku Natori, Ko Fujita, Isao Kitagawa, Kazue Watana ...
1958 Volume 6 Issue 6 Pages
608-611
Published: December 15, 1958
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Pachymic acid which was isolated by Nakanishi, et al. from a Chinese drug"Bukuryo (Fu Ling)"(a sclerotium of Poria cocos (SCHW.) WOLF) has been proved to be 3β-O-acetyl-polyporenic acid-B.
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Torizo Takahashi, Fumiro Yoneda
1958 Volume 6 Issue 6 Pages
611-614
Published: December 15, 1958
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2-, 3-bzw. 4-Oxypyridin wurde mit Quecksilberacetat merkuriert, wobei die Wasserstoffatome des Pyridinrings durch Quecksilber leicht substituiert werden konnten, und zwar wurde 2-Oxy-3, 5-pyridin-bis (merkuriacetat), 3-Oxypyridin-2-merkuriacetat bzw. 4-Oxypyridin-3-merkuriacetat gewonnen. Diese Substanzen wurden durch Behandeln mit gesattigter Kochsalzlosung in Chloride ubergefuhrt, die beim Einwirkenlassen von Jod-Jodkalium-Losung Jodverbindungen, d.h. 2-Oxy-3, 5-dijodpyridin, 2-Jod-3-oxypyridin sowie 4-Oxy-3-merkurijodid, ergaben. Auch liess sich 1, 6-Diazadibenz-p-dioxin aus 2-Jod-3-oxypyridin erhalten.
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Shigehiko Sugasawa, Makoto Kirisawa
1958 Volume 6 Issue 6 Pages
615-618
Published: December 15, 1958
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The preparation of 4-ethyl-and 4-methyl-2 (1H)-pyridones from 4-acetyl-and 4-formyl-pyridine, respectively, was described. Thus the 4-acylpyridines were converted to their etheylene ketal derivatives by the standard method, which were then treated with dimethyl sulfate to give the corresponding 1-methylpyridinium salts. The quaternary salts thus obtained underwent smooth oxidation by alkaline potassium ferricyanide to furnish the 2 (1H)-pyridones, from which 4-acetyl and 4-formyl compounds were recovered through mild acid hydrolysis, and were then reduced according to Huang-Minlon, thus yielding 4-ethyl-and 4-methyl-2 (1H)-pyridones in good yields. Yields were good throughout the entire series of reactions.
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Satoru Kuwada, Toru Masuda, Toyokazu Kishi, Mitsuko Asai
1958 Volume 6 Issue 6 Pages
618-624
Published: December 15, 1958
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The crude enzyme solution, prepared by extracting the ground mycelium of Er. ashbyii with a phosphate buffer and dialyzing the extract against the same buffer solution, was incubated with 6, 7-dimethylribolumazine at 37°. Paper partition chromatography of the reaction mixture gave a yellow and a purple fluorescent spot. The former spot (Rf 0.3 ; solvent-system : EtOH·BuOH·H
2O) was cut out and extracted with hot water, and the ultraviolet spectrum of the extract was measured, showing that it is identical with that of riboflavin. The riboflavin was determined by bioassay with L. casei and by various chemical methods such as the lumiflavin-fluorescence method and others. Next, investigation was made on relationship between quantity of the resulting riboflavin and reaction time, quantity of the crude enzyme solution added, and concentration of the substrate, and further on the optimal pH and temperature for the action of the enzyme solution. Lastly, the above purple-fluorescent spot (Rf 0.23 ; solvent-system : EtOH·BuOH·H
2O) was proved to be that of 6-methyl-7-hydroxyribolumazine, and a new route was proposed for the formation of this compound. Further, the fact that the lumazine derivative was not affected by the crude enzyme solution made more certain the authors'previous assumption that the compound is a final product in the metabolism by Er. ashbyii.
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M. Tomoeda
1958 Volume 6 Issue 6 Pages
624-632
Published: December 15, 1958
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In the preceding paper of this series, it was tentatively assumed, while leaving some doubt, that dl-threo-2-phenyl-4-α-hydroxybenzyl-2-oxazoline isomerized into dl-2-benzamido-3-phenyl-2-propen-1-ol or dl-2-benzimido-3-phenylpropanol in basic media. In this paper, the structure of the isomerization product was corrected to dl-threo-2, 5-diphenyl-4-hydroxymethyl-2-oxazoline by reexamination of chemical properties and final synthesis. The analogous isomerization observed in the optically active p-nitro analogs is a further support for the correction and a possible mechanism of the isomerization without Walden inversion was proposed. dl-threo-2, 5-Diphenyl-4-benzoyloxymethyl-2-oxazoline was found to add benzoyl chloride causing ring opening with Walden inversion to give dl-erythro-2-dibenzoylamino-3-chloro-3-phenylpropyl benzoate.
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Hiroshi Yamanaka
1958 Volume 6 Issue 6 Pages
633-638
Published: December 15, 1958
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Several 4-alkoxy-6-methylpyrimidines were prepared and they were derived to N-oxides by the application of hydrogen peroxide in glacial acetic acid solution or monoperphthalic acid in ether. These were all N-monoxides and were derived to corresponding 4-alkoxy-6-methylpyrimidine-2-carbonitrile by the Reissert reaction. The nitriles so obtained were converted to the corresponding acid amides by treatment with alkaline hydrogen peroxide. Treatment of 4-methoxy-6-methylpyrimidine-2-carbonitrile with sodium methoxide afforded 2, 4-dimethoxy-6-methylpyrimidine, confirming the position of cyano group.
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Hiroshi Yamanaka
1958 Volume 6 Issue 6 Pages
638-641
Published: December 15, 1958
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Reactivity of cyano group in 4-position of 2, 6-dimethylpyrimidine-4-carbonitrile was examined. This compound behaves like ordinary nitriles in forming 4-acetyl compound with methylmagnesium bromide, 4-carboxylic acid ester with dehydrated alcohol and hydrogen chloride, and 4-acid amide with alkaline hydrogen peroxide. However, it showed specificity in undergoing substitution with methoxyl ion to form 4-methoxy compound. The ester or acid amide obtained by such reaction was reacted with hydrazine hydrate to afford 2, 6-dimethylpyrimidine-4-carbohydrazide. Condensation with few other aldehydes was also carried out.
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Tsukasa Kuraishi
1958 Volume 6 Issue 6 Pages
641-644
Published: December 15, 1958
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1) The structures of 3, 4-dichloro-5-aminopyridazine (VIII), m.p. 178, ° and 5, 6-dichloro-3-pyridazinol (III), m.p. 203∼204°, were established. (VIII) was obtained from 4-chloro-5-amino-3-pyridazinol (VI) and was identical with the sample derived from 3, 4, 5-trichloropyridazine ; (IV) was characterized as a convenient intermediate for preparing 5-amino-3-pyridazinol (V) and 3, 6-dichloro-4-aminopyridazine (II). 2) Preparations of 5-amino-6-chloro-3-pyridazinol (IV), 3-chloro-4-hydroxy-5-aminopyridazine (XI), and 2-phenyl-7-chloro-oxazolo [4, 5-d] pyridazine (XII) obtained from (VIII) and (XI) were reported.
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Hiroya Tanabe
1958 Volume 6 Issue 6 Pages
645-648
Published: December 15, 1958
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Majima's amino-anilino-N-phenyl-p-benzoquinone-imine was prepared by treatment of a mixture of o-aminophenol and aniline with silver oxide and it was found that the structure of this quinone-imine is 2-anilino-5-amino-N-phenyl-p-benzoquinone-imine. It was found that the reduction of periodic acid after the critical time in periodic acid oxidation of aniline was caused by this compound.
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Koichi Tomino
1958 Volume 6 Issue 6 Pages
648-652
Published: December 15, 1958
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Under the assumption that the characteristic A-ring in the tetracyclines was responsible for the remarkable antibacterial activity of these antibiotics, syntheses of the A-ring and related compounds were undertaken to examine relationship between chemical structure and antibacterial activity. Following the syntheses of 4-benzamido-, 4-dimethylamino-, and 2-carbamoyl-cyclohexane-1, 3-dione and their derivatives, the A-ring itself of the tetracyclines, 2-carbamoyl-4-dimethylaminocyclohexane-1, 3-dione, and its derivatives were prepared.
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Hiroyuki Inouye, Toshio Arai, Yoshihiro Takano
1958 Volume 6 Issue 6 Pages
653-655
Published: December 15, 1958
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Toluhydrochinon und Pentaacetylglukose wurden in Gegenwart von Amberlite IR-120 oder p-Toluolsulfonsaure im Vakuum erhitzt. Aus dem Reaktionsprodukt liess sich uber einige Stufen das Homoarbutin erhalten. Sein Methylather sowie Pentaacetat wurden ebenfalls hergestellt.
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Hiroyuki Inouye, Yoshihiro Takano
1958 Volume 6 Issue 6 Pages
655-659
Published: December 15, 1958
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Das durch die Kondensation von Tetrahydrogeraniumsaure mit Toluhydrochinon erhaltene d, l-2-Methyl-5-(3, 7-dimethyloctanoyl) hydrochinon lieferte bei der Clemmensen'schen Reduktion das rac-2-Methyl-5-(3, 7-dimethyloctyl) hydrochinon, welches sich mit dem Tetrahydropirolagenin aus Pirolatin als identisch erweist. Dabei wurden auch l-2-Methyl-5-(3, 7-dimethyloctanoyl) hydrochinon und sein Reduktionsprodukt, l-2-Methyl-5-(3, 7-dimethyloctyl) hydrochinon hergestellt.
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Kunio Yagi, Jun Okuda
1958 Volume 6 Issue 6 Pages
659-662
Published: December 15, 1958
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Fluorescence spectra of flavins on paper strip were determined and the peak of the fluorescence spectra of free riboflavin, FMN, and FAD was identically recorded at 530mμ. The relation between the quantity and fluorescence energy on paper strip was linear over a range of the quantities of flavin from 2.66×10
-10 moles to 0.53×10
-11 moles. The relative fluorescence energies of equimolar quantities of free riboflavin, FMN, and FAD on a paper strip were determined under experimental conditions reported herein. The molar quantity of flavins on a paper strip can be determined directly by fluorometry using a standard concentration of free riboflavin placed on the paper strip as a scale.
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Jun Okuda
1958 Volume 6 Issue 6 Pages
662-665
Published: December 15, 1958
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Decomposition of flavin nucleotides in digestive juices was studied. 1. Free riboflavin, FMN, and FAD were not decomposed in saliva. 2. In gastric juice, about 20% of FAD was decomposed to FMN by the hydrochloric acid in gastric juice during 3 hours'incubation at 37° while free ribofiavin and FMN were not decomposed. 3. In bile, 10% of FMN was decomposed to free riboflavin during 2 hours' incubation, free riboflavin and FAD were not decomposed. 4. In pancreatic juice, 45% of FMN was decomposed to free riboflavin during 2 hours' incubation, but free riboflavin and FAD were not decomposed.
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Jun Okuda
1958 Volume 6 Issue 6 Pages
665-669
Published: December 15, 1958
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Decomposition of flavin nucleotides in the small intestine was studied. Free riboflavin was not decomposed at all in the homogenate of the mucosa of the small intestine. FMN was decomposed to free riboflavin very rapidly in the homogenate and FAD was decomposed to free riboflavin through FMN by two steps in the homogenate of the mucosa of the small intestine. Inhibitors for the decomposition of these flavin nucleotides were studied. EDTA, pyrophosphate, and orthophosphate were found to inhibit decomposition of both FMN and FAD in the homogenate. The minimum concentrations of these inhibitors for 50% or 100% inhibition were obtained.
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Tsutomu Momose, Yo Ueda, Tatsuo Shoji, Hiroshige Yano
1958 Volume 6 Issue 6 Pages
669-675
Published: December 15, 1958
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Infrared spectra of 48 benzenesulfonamide derivatives were measured and substituent effect on the SO
2-stretching frequencies was discussed, comparing with those of phenyl sulfone derivatives. The SO
2 frequencies, especially ν
as, of benzenesulfonamide derivatives proved to be in a shorter wave-length region than that of phenyl sulfone derivatives. Electrondonating or-accepting groups attached to the phenyl ring or directly to the sulfonamide group shifted the SO
2 frequencies to a longer or a shorter wave-length region, respectively. The CO streching frequency of N-acetylsulfonamide group showed a large shift to a shorter wave-length region. Synthesis of some benzenesulfonamide derivatives was also described.
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Shoji Inoue
1958 Volume 6 Issue 6 Pages
675-679
Published: December 15, 1958
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5-Chlorothiazolo [5, 4-d] pyrimidine was prepared from 2-chloro-4-mercapto-5-aminopyrimidine (I) and ethyl orthoformate. Ring closure occurred by the reaction of (I), 2, 4-dimercapto-5-aminopyrimidine, 4-mercapto-5-amino-6-chloropyrimidine, or 4-mercapto-5-aminopyrimidine with phosgene, and the corresponding 2-hydroxythiazolo [5, 4-d] pyrimidine derivatives (5-chloro-, 5-mercapto-, 7-chloro-) and 2-hydroxythiazolo [5, 4-d] pyrimidine itself were respectively obtained. When dimercaptothiazolo [5, 4-d] pyrimidines possessing substituents in 2-and 5-positions or in 2-and 7-, were reacted with one mole of ethyl bromide in alkali, substitution occurred only in positions 5-and 7-of the thiazolo [5, 4-d] pyrimidine ring. 2-Thiocyanothiazolo [5, 4-d]-pyrimidine reacted with sodium ethoxide to give 2-mercaptothiazolo [5, 4-d] pyrimidine. Thiazolo [5, 4-d] pyrimidine was obtained by desulfurization of 2-mercaptothiazolo [5, 4-d]-pyrimidine with Raney nickel.
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Shoichi Kanatomo
1958 Volume 6 Issue 6 Pages
680-682
Published: December 15, 1958
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The nature of all six oxygen atoms in enmein, C
20H
26 (28)O
6, were clarified as two of hydroxyls, one of inert ketone, and one of methylene ether ester of hydroxy acid. The discovery of a new group, methylene ether ester of hydroxy acid [chemical formula] seemed of great interest.
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Takeshi Oda, Hiroko Kamiya
1958 Volume 6 Issue 6 Pages
682-687
Published: December 15, 1958
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Lightly autolyzed baker's yeast was extracted with hot ethanol and cerebrine phosphate was isolated from the extract. This ester was compared with cerebrine obtained from penicillin-producing molds to elucidate the chemical structure of cerebrine phosphate. The two substances were similar but the present one extracted from yeast differed from that from the penicillin-producing molds in that it was accompanied by C
18-base and C
20-long chain base, and that its componental fatty acid is a mixture of cerebronic acid (2-hydroxy-C
24-acid) and its homologous 2-hydroxy-C
26-acid. The presence of phosphoric acid is rather interesting.
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Itiro Yosioka, Akiko Zaizen
1958 Volume 6 Issue 6 Pages
688-692
Published: December 15, 1958
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Inhibitory activity of 14 kinds of phenazine derivatives on the growth of Mycobaeterium smegmatis and effect of copper on this activity were examined by shake culture. It was thereby found that the activity of compounds was affected by copper when a hydroxyl was present in 1-position of the phenazine ring and this was considered to be due to formation of a copper chelate. The growth inhibitory activity of the phenazine derivatives themselves and their copper chelates was found to be different from the slope of straight line in concentration-inhibition curves. From the LD
50 of phenazine derivatives, the strongest inhibitory activity was found in compounds having no ability to form a chelate, like 1-and 2-methoxyphenazine.
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Haruo Saikachi, Keizo Suzuki
1958 Volume 6 Issue 6 Pages
693-696
Published: December 15, 1958
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Nineteen kinds of 3-(5-nitro-2-furyl) acrylamides were prepared by condensation of 3-(5-nitro-2-furyl) acryloyl chloride and alkylamines. Among these acid amides, N-(2-hydroxypropyl)-3-(5-nitro-2-furyl) acrylamide (XIX) showed a higher solubility in water and a strong antibacterial activity.
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Tsutomu Furuya
1958 Volume 6 Issue 6 Pages
696-700
Published: December 15, 1958
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Dimethylesculetin was demethylated in the rabbit to give esculetin 7-methyl ether, scopoletin, and esculetin. The free and conjugated forms of each metabolite were determined directly by a densitometer applied on the paper chromatogram. The urinary metabolites obtained from scopoletin have also been examined.
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Tsutomu Furuya
1958 Volume 6 Issue 6 Pages
701-706
Published: December 15, 1958
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Studies on the metabolic fate of coumarin and dihydrocoumarin have been elucidated. Coumarin was mainly hydroxylated to 3-hydroxycoumarin, umbelliferone, and a trace of 8-hydroxycoumarin. o-Coumaric acid was subjected to opening of the lactone ring and glycine conjugates of o-coumaric acid and melilotic acid were detected in the metabolite. Hydroxylated compounds were conjugated with glucuronic and sulfuric acids. Various metabolites derived from dihydrocoumarin were also detected by paper chromatography. A scheme of metabolic process of coumarin and dihydrocoumarin was also proposed and discussed.
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Tsutomu Furuya
1958 Volume 6 Issue 6 Pages
706-710
Published: December 15, 1958
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A study on the metabolic fate of o-coumaric acid and melilotic acid has been carried out. The urinary metabolites after o-coumaric acid dosing were determined to consist of unchanged o-coumaric acid (20.22% of dose), o-coumaric acid glucuronide (3.45%), o-coumaroylglycine (11.06%), melilotic acid (8.18%), umbelliferone (1.92%), umbelliferone glucuronide (2.62%), and coumarin (0.96%). Using paper chromatography, the presence of 4-hydroxycoumarin and melilotoylglycine was detected, but 3-hydroxycoumarin was not found. Coumarin and umbelliferone were found in the urine after o-coumaric acid dosing. A cis-trans transformation might be involved in the metabolic process. On dosing melilotic acid, unchanged melilotic acid, o-coumaric acid, melilotoylglycine, o-coumaroylglycine, umbelliferone, 4-hydroxycoumarin, coumarin, and dihydrocoumarin were detected in the urine. Biochemical transformations of o-coumaric and melilotic acids as well as that of coumarin and dihydrocoumarin were discussed.
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Tomoharu Okuda, Kokichi Ashino, Yoshiyuki Egawa, Makoto Suzuki
1958 Volume 6 Issue 6 Pages
711-715
Published: December 15, 1958
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From the fermentation broth of Streptomyces naraensis nov. sp. two antiyeast antibiotics, named Naramycin-A and-B, were obtained. Of these antibiotics, Naramycin-A was identified with cycloheximide (Acti-dione) reported by Leach, et al. Taxonomic studies of Streptomyces naraensis were described.
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Keijiro Takagi, Issei Takayanagi, Kyo Fujie
1958 Volume 6 Issue 6 Pages
716-720
Published: December 15, 1958
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(1) Tracheal strip preparation was proved to respond very sensitively to acetylcholine (ACh) and histamine. It is more suitable to test drug action on tracheal smooth muscle than tracheal chain. (2) From the present experimental results and on applying Ferguson's rule, the papaverine-like antispasmodic action, which is tested ordinarily against barium contraction of ileum, must be divided into two categories ; (a) the nonspecific inhibitory action, which is exerted by some physicochemical property of non-ionized molecules and can be tested on tracheal muscle, and (b) the specific unsurmountable inhibitory action, which is exhibited by ionized molecules of strong bases and can be tested on ileum. (3) Neutral esters such as isoamyl esters and weak bases such as papaverine exist as non-ionized molecules in physiological pH, and they have only nonspecific inhibitory action on any smooth muscles. Strong bases such as tertiary amines are ionized as much as 90% of the total amount in physiological solution. They exert specific but unsurmountable inhibitory action on ileum by their cation and exhibit non-specific action on tracheal muscle through their neutral base.
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Den-itsu Shiho, Noboru Takahayashi, Rikuko Honda, Reiko Morikawa
1958 Volume 6 Issue 6 Pages
721-722
Published: December 15, 1958
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Noboru Takahayashi, Rikuko Honda
1958 Volume 6 Issue 6 Pages
722-724
Published: December 15, 1958
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Kyosuke Tsuda, Saburo Akagi, Yukichi Kishida, Ryoichi Hayatsu, Kiyoshi ...
1958 Volume 6 Issue 6 Pages
724-727
Published: December 15, 1958
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Torizo Takahashi, Kanichi Ueda, Ryota Oishi, Katsumaro Minamoto
1958 Volume 6 Issue 6 Pages
728
Published: December 15, 1958
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Kyozo Hayashi
1958 Volume 6 Issue 6 Pages
729-730
Published: December 15, 1958
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Eiji Ochiai, Toshihiko Okamoto, Masahide Kaneko
1958 Volume 6 Issue 6 Pages
730-731
Published: December 15, 1958
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Yoshiro Kobayashi
1958 Volume 6 Issue 6 Pages
732-734
Published: December 15, 1958
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