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Hideyo Shindo
1958 Volume 6 Issue 2 Pages
117-128
Published: April 20, 1958
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Infrared spectra of substituted pyridine 1-oxides with various kinds of substituent mainly at 3- or 4-position were determined. Their N-O stretching frequencies (strong absorption in the region of 1200 and 1300cm
-1) were found to be correlated with the nature of a substituent, and a linear relation between these frequencies and σ-values of the substituents was pointed out. The ring C-H out-of-plane bending frequencies of these compounds showed a regular shift from those of the parent pyridines, shifting always to a higher frequency in 2- and 4-substituted derivatives, and always to a lower frequency in 3-substituted derivatives. Absorptions in the regions of 900∼1200cm
-1 and 1450∼1630cm
-1 were also correlated with the structure. From a comparison of the frequency shift in a characteristic vibration of the ring substituent, the σ-values of 0.25 and 1.18 were respectively obtained for 4- and 3-positions of pyridine 1-oxides. All these points were discussed in terms of an electronic effect of the N-oxide function.
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Jun Hasegawa, Tsuneji Nagai
1958 Volume 6 Issue 2 Pages
129-137
Published: April 20, 1958
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The effect of added substance (S) and pH (P) of the vehicle, and temperature (T) and period (M) of preservation on the change of mean diameter of suspended particles was investigated with a sulfadiazine suspension, and the following conclusions were drawn : 1) The distribution of particle size was logarithmic normal throughout the determinations, the same as in the starting material. 2) As a result of factorial analysis of the mean diameter, main effects P, T, and M were highly significant and interaction P×T was significant. 3) The same result was obtained on the analysis of standard deviation. 4) A highly significant negative correlation was found between the mean diameter and standard deviation. 5) As observed in this study, it may be considered that there is a maximum to the increase of particle size and the tendency is represented as follows : [numerical formula] where e is the factor promoting the change of mean diameter d, and k, A, B, and I are constants which are expected to be influenced by physical and chemical properties of the material used, the vehicle, and other conditions.
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Takashi Uemura, Tomomichi Yanagita
1958 Volume 6 Issue 2 Pages
138-142
Published: April 20, 1958
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The growth responses of bacteria to various B vitamins were found to be classified into four groups. In Type I the growth is affected only in shortening the lag phase of cultural development, in Type II the rate of logarithmic growth and the yield of final population are promoted, and in Type III only the final yield is enhanced leaving other phases of growth unaffected. These types of growth promotion seemed not to be a fixed character of a vitamin. Several examples showing the variability of the type for a vitamin according to the cultural conditions were presented. Physiological interpretation of these types of growth promotion was discussed. Finally, importance of the choice of test system for the turbidimetric bioassay of vitamin was suggested from the view-point of the proposed types of growth promotion.
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Goro Chihara
1958 Volume 6 Issue 2 Pages
143-147
Published: April 20, 1958
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Minimization of samples for infrared spectral measurement was attempted by the use of a Japanese folkcraft, hand-made paper, impregnated with liquid paraffin. By this method, it is possible to measure 0.1 mg. of a sample. This hand-made paper was also used for paper chromatography and the developed paper was submitted directly to infrared spectral measurement. Component of Penicillium islandicun and inorganic sulfate ion were determined by spectral measurement of their chromatogram.
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Yutaka Kasuya
1958 Volume 6 Issue 2 Pages
147-154
Published: April 20, 1958
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1. Fifty-eight aralkylamines were tested for atropine-like activity against acetylcholine-stimulated ileal strips of mice. 2. Papaverine-like activity of the aralkylamines was tested against excess acetylcholine-stimulated ileal strips of mice. 3. The relationship between chemical structure and pharmacological activity has been discussed. In almost all the compounds tested here, atropine-like activities change somewhat parallel with the papaverine-like activities of the compounds. The effect of quaternization of tertiary amines is the only exception, where the quaternary ammonium compounds have stronger atropine-like and weaker papaverine-like action than the corresponding tertiary amines. It is suggested that some physicochemical properties such as lipoid solubility would influence the papaverine-like activity and also participate even in intensifying the atropine-like antiacetylcholine activity.
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Yutaka Kasuya
1958 Volume 6 Issue 2 Pages
155-159
Published: April 20, 1958
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The cationic properties of aralkylamines were compared approximately by paper electrophoresis. These compounds were broadly divisible into four groups on the basis of their mobilities. Biological characteristics of each group were discussed.
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Ryuichi Kimura, Takahiro Yabuuchi, Yasutaka Tamura
1958 Volume 6 Issue 2 Pages
159-163
Published: April 20, 1958
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It was found that 3-piperidino-1, 1-di (2-thienyl) butene prepared by Adamson possessed an antitussive action. The compound has one amino group at the 3-position, and one double bond between 1 and 2. However, ephedrine used as an antitussive for a long time has one amino group at 2-position and a hydroxyl group at 1-position. Therefore, 2-amino-1, 1-di (2-thienyl) propanols and 2-amino-1, 1-di (2-thienyl)-ethanols which have one amino group at 2-position and hydroxyl group at 1-position were synthesized, in order to investigate the structure-activity relationship of the antitussive. The compounds were synthesized by the condensation of 1-aminoalkane-1-carboxylic acid esters and thiophene (the lithium method).
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Morizo Ishidate, Yoshio Sakurai, Kozo Maruyama
1958 Volume 6 Issue 2 Pages
164-169
Published: April 20, 1958
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Preparation, chemical properties, and carcinostatic activity on the Yoshida sarcoma of N, N'-bis(2-chloroethyl)-N, N'-dimethylpolymethylenediamines were discussed. It was concluded that the derivatives of hexamethylenediamine and nonamethylenediamine were more promising than the corresponding lower homologs with respect to chemotherapeutic indices.
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Morizo Ishidate, Yoshio Sakurai, Kozo Maruyama
1958 Volume 6 Issue 2 Pages
169-172
Published: April 20, 1958
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Preparation of N, N'-bis (2-chloroethyl)-N, N'-dimethylpolymethylenediamine N, N'-dioxides was described and the relation between the process of characteristic transformation reaction and biological action of these compounds was discussed.
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Atsuji Okano
1958 Volume 6 Issue 2 Pages
173-177
Published: April 20, 1958
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Of the 17 kinds of unknown cardiotonic glycoside-like substances contained in the seeds of Digitalis purpurea, described in Part II of this series, a glycoside corresponding to substance A-IX was isolated. This substance was not obtained in crystalline form, but by the usual deacetylation of its acetate, monoacetate came as needle crytals of m.p. 249∼252° (Kofler, uncorr.) ; [α]
24D-14.2°±3° ; C
44H
68O
20·H
2O ; negative to Keller-Kiliani reaction, giving carmine red sulfuric acid layer, and positive to Legal and Raymond reactions ; U.V. λ
EtOHmax218mμ (log ε 4.18). These results indicated the substance to be a cardiotonic glycoside. Its hydrolysis with 3.5% hydrochloric acid afforded dianhydrogitoxigenin and the sugar portion was found to be digitalose and glucose by paper partition chromatography. Determination of glucose showed the presence of two moles. Therefore this substance was found to be a new glycoside, an isomer of gitostin which was reported in Part III, and was named neogitostin. Gitostin monoacetate was prepared and compared with neogitostin monoacetate. By paper chromatography for strong polar glycoside portion, a new spot was confirmed between the spots of gitostin and neogitostin, and numbered A-VIII'.
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Atsuji Okano
1958 Volume 6 Issue 2 Pages
178-182
Published: April 20, 1958
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The structure of neogitostin, newly isolated from digitalis seeds by the writer and described in the preceding paper, was examined by enzymatic decomposition using the same enzyme isolated from a snail (Euhadra quaesita DESHAYES) as described in Part IV of this series. It was found that hydrolysis of amorphous neogitostin afforded strospeside and digitalinum verum. However, hydrolysis of monoacetates of gitostin and neogitostin, under the same conditions as those used in the partial decomposition of gitostin to form digitalinum verum but by shortening the duration of hydrolysis, glucose alone was found to be hydrolyzed from these monoacetates, affording digitalinum verum monoacetate. From these results, it was found that gitostin and neogitostin are isomeric triglycosides whose terminal glucose is linked to the terminal glucose in digitalinum verum. By respective acetolysis of gitostin nonaacetate and neogitostin nonaacetate, it was established that gitostin is gitoxigenin-β-cellobiosido-β-D-digitaloside and neogitostin is gitoxigenin-β-gentiobiosido-β-D-digitaloside.
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Masao Murayama
1958 Volume 6 Issue 2 Pages
183-186
Published: April 20, 1958
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Isoquinoline cyclization of N-(3, 4-dimethoxyphenethyl)-2-ethoxycarbonylacetamide and 2-alkyl and 2-dialkyl derivatives was studied. Contrary to expectations, the cyclization of dialkyl-substituted acetamide derivatives proceeded most smoothly with excellent yield of the product. One of such products, ethyl α, α-diethyl-α-(6, 7-dimethoxy-3, 4-dihydro-1-isoquinolyl) acetate, resisted all attempts at dehydrogenation and the starting dihydro base was recovered quantitatively. β-Diethylaminoethyl α, α-diethyl-α-(6, 7-dimethoxy-3, 4-dihydro-1-isoquinolyl) acetate was also prepared for pharmacological evaluation.
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Masao Murayama
1958 Volume 6 Issue 2 Pages
186-194
Published: April 20, 1958
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A series of 1-tert-alkyl-6, 7-dimethoxy-3, 4-dihydroisoquinolines was synthesized in high yields by cyclizing N-(3, 4-dimethoxyphenethyl)-2, 2, 2-trialkylacetamides with phosphoryl chloride. They were dehydrogenated over palladium-carbon only under strenuous conditions to furnish the corresponding isoquinolines. Their spasmolytic activity will be examined. A general procedure for the preparation of trialkylacetic acids of high purity was also described.
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Shigehiko Sugasawa, Masao Murayama
1958 Volume 6 Issue 2 Pages
194-200
Published: April 20, 1958
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N-Methyl-α-bromo-γ-phthalimidobutyranilide (X) was treated with fused aluminum chloride according to the method of Stolle, giving the corresponding oxindole derivative (XI), from which the phthalimido group was removed smoothly by Ing's method. When the amine (XII) thus prepared was treated with metallic sodium 1-methyltryptamine was produced in a fair yield as the sole isolable product and the expected cyclized product, dl-nordesoxyeseroline (A), once supposed as folicanthine, was not traced in the reduction product. However, when 1, 3-dimethyl-3-(β-methylaminoethyl) oxindole (VIII), prepared in a silmilar manner as (XI), was subjected to the same reduction, there was obtained dl-esermethole (IX), which had already been prepared by Preobrazhenskii, et al. a few years ago by a different method. The presence or absence of a hydrogen atom at 3-position of oxindole derivatives was thus shown to be a decisive factor for the course of their reduction.
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Shigehiko Sugasawa, Masao Murayama
1958 Volume 6 Issue 2 Pages
200-203
Published: April 20, 1958
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α-Bromo-α-methyl-δ-phthalimidovaler-p-anisidide (VIII) was fused with aluminum chloride according to Stolle to give 5-methoxy-1, 3-dimethyl-3-(γ-phthalimidopropyl) oxindole (IX) after methylation. Phthalimido group could be readily removed from this compound by the standard method, furnishing 3-(γ-aminopropyl) oxindole derivative (X), which was then monomethylated to (XI). This compound could also be prepared advantageously by reducing 5-methoxy-1, 3-dimethyl-3-(β-cyanoethyl) oxindole (XII) catalytically in the presence of methylamine. On being reduced with sodium in boiling ethanol the latter gave rise to a single dl-homoesermethole (III) in a fair yield, no isomeric base being detected in the reduction product.
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Osamu Tanaka
1958 Volume 6 Issue 2 Pages
203-208
Published: April 20, 1958
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The structures of dialkylpseudoskyrin and its related compounds were discussed and it was shown that all the evidences provided agreed quite sufficiently with the structure proposed in the previous paper. The mechanism of the coloration of skyrin with conc. sulfuric acid was also discussed using some model compounds (tetraacetylbirubiadin-(4, 4'), etc.).
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Eiji Ochiai, Masayuki Ishikawa
1958 Volume 6 Issue 2 Pages
208-213
Published: April 20, 1958
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Cinchonin wurde uber 2'-Hyroxydihydrocinchonin und 2'-Oxohexahydrocinchonin in Dihydrocinchonamin ubergefuhrt.
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Katsumi Tanabe
1958 Volume 6 Issue 2 Pages
214-217
Published: April 20, 1958
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Alantolactone was converted to dihydroeudesmol and it was confirmed that the alantolactone series belongs to the trans-fused decalin type.
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Katsumi Tanabe
1958 Volume 6 Issue 2 Pages
218-221
Published: April 20, 1958
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The methyl group in 4-position of tetrahydroalantolactone and the so-called β-tetrahydroalantolactone was confirmed to be respectively β- and α-orientated. Several 3-hydroxytetrahydroalantolactones were prepared.
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Yoshinobu Sato
1958 Volume 6 Issue 2 Pages
222-223
Published: April 20, 1958
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Tyunosin Ukita, Makoto Miyazaki, Mieko Hashi
1958 Volume 6 Issue 2 Pages
223-224
Published: April 20, 1958
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Kyosuke Tsuda, Masaaki Kawamura, Ryoichi Hayatsu
1958 Volume 6 Issue 2 Pages
225-226
Published: April 20, 1958
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Masamoto Nishikawa, Hikoichi Hagiwara
1958 Volume 6 Issue 2 Pages
226-228
Published: April 20, 1958
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