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MASAYUKI NAKAGAKI, HISAKAZU SUNADA, AKIRA KONDO, JUN-ICHI TERAO
1969 Volume 89 Issue 2 Pages
139-144
Published: February 25, 1969
Released on J-STAGE: May 30, 2008
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A mixture of water and alcohol containing sodium iodide was selected as the precipitant to be used in fractional precipitation of sodium carboxymethyl cellulose. The condition of fractionation was examined and raw sodium carboxymethyl cellulose was divided into eleven fractions. The substitution degree and molecular weight of each fraction were measured. From these results the molecular weight distribution in the raw material was obtained. Then, the turbidimetric titrations of the fractions 2, 4, 6, 8 and 10 were carried out. From these results, it was obtained that the relation between log C
p and (v
2) ppt, where C
p is the polymer concentration and (v
2) ppt is the volume fraction of the precipitant added when the precipitation starts, was linear for each polymer fraction and parallel to one another. These results were in good agreement with Morey-Tamblyn's empirical equation. The final equation obtained for this system was ; (v
2) ppt=-0.050 log C
p+0.918 M
-0.954.
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KOICHI MARUYAMA, KOICHI KISHIMOTO, AKIRA TANAKA, GORO URAKUBO, OSAMU I ...
1969 Volume 89 Issue 2 Pages
145-153
Published: February 25, 1969
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Changes in norphenylephrine concentration in the serum of the rabbit, rat, and guinea pig were measured and the half-life of norphenylephrine was determined. Orally administered norphenylephrine was rapidly absorbed in the serum with concentration reaching the maximum level with in 1 hour (Fig. 1, 4, and 5), and no detectable amount was found 24 hours. The half-life of norphenylephrine was found to be 3.5, 4.6 and 4.2 hr in the rabbit, rat, and guinea pig, respectively. Urinary excretion rate of norphenylephrine was studied using
3H-labeled norphenylephrine in the rat, and it was found that 12.3% of
3H-norphenylephrine was excreted within 24 hours with approximately 85% of this amount appearing within 4 hours after intraperitoneal administration. Vasopressive reaction was observed after oral and enteric administration of norphenylephrine, but this was particularly marked in the case of enteric administration (Fig. 8). These results indicated that norphenylephrine administered orally was mainly absorbed through the intestine, and that the norphenylephrine absorbed exerted a vasopressive action. Determination of urinary epinephrine showed that the administration of norphenylephrine had no effect on epinephrine excretion.
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TETSUJI KAMETANI, KAZUYA YAMAKI, KUNIO OGASAWARA
1969 Volume 89 Issue 2 Pages
154-157
Published: February 25, 1969
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By the use of the method for synthesizing alkoxylated benzyl cyanide by the benzyne reaction of alkoxylated halogenobenzenes and acetonitrile, the objective 4, 5-dimethyoxy-2-formylbenzyl cyanide was synthesized by the benzyne reaction of 6-bromoveratraldehyde (IV) or 6-bromoveratraldehyde acetal (V) and acetonitrile under the same conditions. It is interesting that, in this reaction, a naphthalene derivative was obtained from IV and a structurally unknown basic substance (X or Xa) from V with the objective compound.
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MIKIO TAKEDA, MITSURU MATSUBARA, HIROSHI KUGITA
1969 Volume 89 Issue 2 Pages
158-163
Published: February 25, 1969
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On the basis of earlier finding that an alkylsulfonyl group when introduced into simple benzene derivatives exerted a CNS activity, ethylsulfonyl derivatives of dibenzo [b, e]-[1, 4] diazepines (VII, VIII, and X) were synthesized. A dimethylsulfamyl derivative (XX) was also prepared for comparison. VII (R=CH
3, n=2) was selected as a potent anti-depressant with low toxicity.
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TAMEYUKI AMANO, TOSHIYUKI SAKANO
1969 Volume 89 Issue 2 Pages
164-172
Published: February 25, 1969
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Phosphorescence and fluorescence at 77°k were compared in 2-phenylphthalimidines having a substituent (OH, OCH
3, CH
3, H, Cl, Br, I, COOH, SO
2NH
2, NO
3, 2', 3'-benz., 3', 4'-benz.) in the phenyl group at 2-position. Mean life time of the phosphorescence of 2-(m- or p-halogenophenyl) phthalimidines showed the internal heavy atom effect of the substituted atoms and the mean life time decreased in the order of chlorine, bromine, and iodine. The life time of p-halogen substituted compounds was smaller than that of m-halogen compounds. Based on these facts phosphorimetric determination of m-iodoaniline was devised which relied on the phosphorescence reaction by the formation of 2-phenylphthalimidines from phthaladehyde and aromatic primary amines in sulfuric acid-ethanol solution. This phosphorescence method was not interfered by ο-iodoaniline, p-iodoaniline, N-methylaniline, N, N-dimethylaniline, benzylamine, or urea, and its selectivity was better than that of fluorescence method.
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TSUKINAKA YAMANA, YUZO MIZUKAMI, FUJIO ICHIMURA
1969 Volume 89 Issue 2 Pages
173-181
Published: February 25, 1969
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Through the detection of the coloring of glucuronic acid (GH) by the hydroxamic acid method, degradation of glucuronamide was reexamined. The reaction scheme GN→GH ⇄ GL proposed in the previous paper was corrected as [numerical formula] where GL is glucuronic acid lactone and G- the glucuronate ion. By determinating of the influence of pH and buffer concentration on the rate constants, the following equation was obtained.[numerical formula]
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TATSU KAWANO, KIKUYO MORIWAKI, KIKUKO EBISU, KAZUKO WATANABE
1969 Volume 89 Issue 2 Pages
182-187
Published: February 25, 1969
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Eighteen kinds of the free L-amino acids found in extracts and hydrolysates of fasted silkworm feces, and those in the extracts of mulberry leaves were determined by microbiological assay. As the amount of histidine and serine in the extracts was equal to that in the hydrolysates and the amount of the others in the hydrolysates was more than that in the extracts, we concluded that histidine and serine were excreted in the free form and the other amino acids in the free and combined form. Monoamino-dicarxylic-acids, glutamic acid and aspartic acid, were found in a relatively higher amount, but sulphur-containing amino acids, cystine and methionine, were found in a small amount in silkworm feces and mulberry leaves. Histidine in the extracts and glycine in the hydrolysates were markedly abundant, these amino acids being about 26% of the total amino acids. There seemed to be direct relationship between the amount of the previous amino acids excreted and those taken from mulberry leaves, while there seemed to be certain parallel relationship between the amount of the other amino acids found in the feces and the body fluid and that of amino-acids contained in the mulberry leaves. These facts suggest us that histidine and glycine are biosynthesized from other compounds in silkworm body. It is interesting to found that glycine is excreted in high amount as glycine is involved in the biosynthesis of fibroin and abundantly accumulated in the silkworm body.
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TETSUZO KATO, TAKAYUKI SHIRAISHI, TOSHIO ATSUMI
1969 Volume 89 Issue 2 Pages
188-193
Published: February 25, 1969
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Reaction of 2-pyridineacetonitrile (II) with aldehydes in the presence of sodium hydroxide or piperidine in ethanol gives α-alkylidene-2-pyridineacetonitrile (V). II does not react with ketones under the same condition but does react with benzophenone in the presence of sodium amide to give α, α-diphenyl-2-pyridineethanol (IX). II easily transits to α-acyl-2-pyridineacetonitrile (X) by reaction with acid halides. Catalytic reduction, hydrolysis, and Grignard reaction of V are also described.
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TOZABURO KURIHARA, HIDEO TAKEDA, KEIKO SAGAWA, KATSUICHI MATSUO, TOMON ...
1969 Volume 89 Issue 2 Pages
194-202
Published: February 25, 1969
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Nineteen different-compounds were synthesized and some of their pharmacological properties as local anesthetic activities, analgetic activities, antibiotic activities, acute toxicities, influences on blood pressure-were investigated. Three of them were found to have a longer action in both topical and infiltratic anesthesia than Lidocaine. The duration of infiltratic anesthesia of compounds No. 1, 14, 18 were three times as long as Lidocaine. The conductive anesthetic and recovery processes of sample No. 1 tested on bullfrog sciatic nerve were similar to those of Lidocaine. The recovery of dichloro-derivatives was inferior to that of monochloro-derivatives. In general acute toxicities of these compounds increased as the number of carbon atoms in diamino-radicals increased. Almost all of these compounds showed on the hot plate test remarkable elevation of pain threshold when 70 mg were injected to mice. Blood pressure of the dog was depressed temporarily and slightly by administration of 1 to 3 mg of these substances, but no antimicrobial activity was observed.
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GORO KOBAYASHI, SUNAO FURUKAWA, YOSHIRO MATSUDA, SHOTARO MATSUNAGA
1969 Volume 89 Issue 2 Pages
203-208
Published: February 25, 1969
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2-Pyridineacetonitriles (I) were derived to their sodium salts and reacted with carbon disulfide and dimethyl sulfate to prepare α-bismethylthiomethylene-2-pyridineacetonitriles (II) (cf. Table I). II reacted with amines to form III, IV, and V (cf. Table II). Reaction of I and methyl 1-cyano-2, 2-dimethylthioacrylate (IX) gave 2-methylthio-3-cyano-4H-quinolizin-4-ones (XI)(cf. Table III). XI reacted with various amines to form XV (cf . Table V).
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SHIGERU SHIMOMURA, YOSHIKO FUKUMOTO
1969 Volume 89 Issue 2 Pages
209-214
Published: February 25, 1969
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In the case of the determination of iron with Co (III)-NTA complex, the end point for iron was obtained as a break of the photometric titration curve at 550 mμ, and the result was not affected by addition of 0.53 g of ascorbic acid 11 mg of Fe (II). So that this method is suitable for the determination of iron in the presence of ascorbic and such acid. This determination was not interfered with such ions as Co (II), Cu (II), and Mn (II), compounds as nicotinamide, vitamin B
0 vitamin B
1 hydrochloride, DL-methionine, calcium pantothenate, and D-sorbitol. Applying this method to the determination of iron in the hematinics, analytical results correspond well with that obtained by the ο-phenanthroline method.
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TAKEO MORIMOTO, MASAAKI YAMAMOTO
1969 Volume 89 Issue 2 Pages
215-221
Published: February 25, 1969
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Urogastrone was isolated from pregnant human urine by the sequential steps of benzoic acid adsorption, acetone fractionation, DEAE-cellulose chromatography, and gel filtration. The preparation so obtained was free from gonadotropin activity. Comparative examination of urogastrone isolated from pregnant and non-pregnant human urine by the present method and other known methods showed that the present method gave a preparation with high unit activity in a high yield, free from gonadotropin activity. The yield of purified urogastrone by this method was 1.5 mg/liter from pregnant urine and 1.3 mg/liter from non-pregnant urine, and their inhibitory activities were 0.25 and 1.0 mg/kg, respectively. Yield of total inhibitory activity from the pregnancy urine was approximately five times that from non-pregnancy urine by the present method while this was about three times by the known method. These facts indicate the high urogastrone content in the urine during pregnancy. The purified urogastrone obtained in the present experiment from pregnancy urine was found to be practically homogeneous by electrophoretic analysis, and is a high-molecular glycoprotein containing 20% of sugar, with an isoelectric point at pH 3.5.
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MASAYOSHI KOBAYASHI, MASAAKI YAMAMOTO
1969 Volume 89 Issue 2 Pages
222-229
Published: February 25, 1969
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Human saliva was separated into dialyzable and nondialyzable fractiona ; the non-dialyzable fraction was found to possess a powerful activity of inhibiting gastric acid secretion and ulceration. This active substance, designated as sialogastrone, was purified by sequential steps of zinc complex precipitation, acetone fractionation, DEAE-cellulose column chromatography, and gel filtration. The purified sialogastrone so obtained possessed inhibitory activity 300 times that of the original lyophilized saliva. This preparation was found to be almost homogeneous by polyacrylamide-gel electrophoresis and showed electrophoretic mobility different from that of other neutral substances in saliva. This purified sialogastrone contained 58.6% of reducing sugars and 31.5% of protein, but no phosphorus or lipids. Its molecular weight was assumed to be over 150, 000 from the result of gel filtration.
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TETSUJI KAMETANI, HIDEO IIDA, SADAO TANAKA
1969 Volume 89 Issue 2 Pages
230-234
Published: February 25, 1969
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Double Ullmann reaction of 1-[3-(4-benzyloxy-3-bromophenyl) propyl]-1, 2, 3, 4-tetrahydro-7-hydroxy-6-methoxy-2-methylisoquinoline (II) afforede two diastereoisomeric O, O-dibenzyloxyhomomelanthioidines (Va and Vb) by forming twenty two-membered ring system, the structures of which were confirmed by IR, NMR, and Mass spectra. Removal of Benzyl group by treating Va and Vb with hydrochloric acid gave the corresponding diastereoisomeric homomelanthioidines (VIa and VIb), respectively. The synthesis of II was also described.
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HIROSHI HIKINO, SUSUMU NABETANI, KYOSUKE NOMOTO, TOMIO ARAI, TSUNEMATS ...
1969 Volume 89 Issue 2 Pages
235-240
Published: February 25, 1969
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Longterm feeding of insect-metamorphosing substances, ecdysterone and cyasterone, slightly increased the growth of mice without any toxicity, when administered in doses of 5-100 μg/day/animal. Daily administration of these steroids even in a dose of 5μg/animal maintained protein synthesis in liver and kidney in an elevated level. Histological examinations of liver tissues after a 90 day administration revealed that metabolism of the cells was activated by ecdysterone and cyasterone.
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TAKEHISA CHIBA
1969 Volume 89 Issue 2 Pages
241-247
Published: February 25, 1969
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1) S-S compounds such as oxidized glutathion, oxidized 2-mercaptopropionylglycine, and cystine were administered to normal and alloxan-diabetic rabbits, and the variations of blood sugar value, and of acid-soluble SH and S-S groups in the blood were observed for one week. Compounds which accelerate the liberation of insulin and compounds which antagonize the insulin action were also examined in the same manner. 2) Administraion of S-S compound to the normal rabbit resulted in no change of the blood sugar amount, decrease of SH groups and increase of S-S groups which recovered a normal level after 24 hr ; administration of S-S compounds to alloxan diabetic rabbits decreased SH groups which did not recover a normal level even after 24 hr. Blood sugar level tended to rise with the repetition of the administration. 3) compounds which have insulin action and compounds which accelerate the liberation of insulin by stimulating the pancreatic β cells, increase the S-S groups and decrease or do not affect the SH groups in normal rabbits (insulin, glucose, alloxan). In diabetes, both SH and S-S groups increase (insulin, R-SH). 4) Compounds which antagonize insulin action tend to decrease S-S groups (adrenalin, glucagon).
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TAKEHISA CHIBA
1969 Volume 89 Issue 2 Pages
248-253
Published: February 25, 1969
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1) Effect of SH and S-S compounds on the passage of sugars through the cell membrane was examined by the use of rat diaphragm and epididymal adipose tissue. 2) Both SH and S-S compounds, in the absence of insulin, accelerate the passage of sugars through the membrane and this accelerative effect is also observed in DNP and PCMB. 3) This accelerative action of SH and S-S compounds is also observed in alloxan-diabetes rat tissue, as well as in normal rats. 4) Sugars (L-arabinose, D-xylose) which have a stereospecificity in membrane passage and whose activity is accelerated by insulin are also accelerated by SH compounds. 5) Sugars in the cells are rapidly expelled outside the cells by SH compounds. From these results we discussed the way of action of thiol and disulfide compounds on the passage of sugars through the cell membrane in respect to the SH group of the cell membrane and the insulin action.
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SHIGEO SENDA, HIROSHI IZUMI, TAKEO TANIMOTO, HAJIME FUJIMURA
1969 Volume 89 Issue 2 Pages
254-259
Published: February 25, 1969
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As the assumed metabolites of bucolome (I), the compounds (V and XXVIII) formed by the oxidation of 1-cyclohexyl to 1-(4-hydroxycyclohexyl) or 1-(p-hydroxyphenyl) group were synthesized. At the same time, series of related compounds were systematically prepared and relationship between their chemical structure and their anti-inflammatory action and acute toxicity was examined. V was indentified as one of the metabolites of bucolome by the collaborators and details of this work will be published elsewhere.
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SHIGEO SENDA, HIROSHI IZUMI, HAJIME FUJIMURA
1969 Volume 89 Issue 2 Pages
260-265
Published: February 25, 1969
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As the assumed metabolites of bucolome (I), the compounds (III to VI) formed by the oxidation of 5-butyl to 5-(3-oxobutyl), the compounds (XXI to XXIV) formed by the oxidation of 5-butyl to 5-(3-hydroxybutyl), and the compounds (XXVII and XXVIII) formed by the oxidation of 5-butyl to 5-(4-hydroxybutyl) group were synthesized. At the same time, a series of related compounds were systematically synthesized and the relationship between their chemical structure and their pharmacological action (anti-inflammatory activity) and acute toxicity was examined. XXII was identified as the main metabolite of bucolome by collaborators and details of this work will be published elsewhere.
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SHIGEO SENDA, HIROSHI IZUMI
1969 Volume 89 Issue 2 Pages
266-271
Published: February 25, 1969
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Heating of 1-cyclohexyl-5-(3-hydroxybutyl)-perhydropyrimidine-2, 3, 4-trione (II) in methanol, in hydrochloric acidity, results in facile liberation of one mole of water to form a high-melting compound (III), mp 287°, which was assumed to be 3-cyclohexyl-7-methyl-1, 2, 3, 4, 6, 7-hexahydro-5H-pyrano [2, 3-d] pyrimidine-2, 4-dione (IIIa) from its infrared and ultraviolet spectra, and pK
a value. The foregoing dehydrative cyclization reaction was used to synthesize and series of related compounds and some examinations were made on the chemical structure of these substances.
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SHIGEO SENDA, HIROSHI IZUMI, KOSAKU HIROTA
1969 Volume 89 Issue 2 Pages
272-278
Published: February 25, 1969
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Syntheses were carried out on the assumed metabolites of bucolome (I) which comprised : (A). Compounds (XII, XIV, XVII) in which the butyl group in 5-position had been oxidized to 3-carboxypropyl, 2-carboxyethyl, or carboxymethyl group, and their derivatives (XI to XVIII), (B) the compound (XXV) in which the hydrogen atom in 5-position had been oxidized to the hydroxyl group, and compounds related to it (XXIV to XXXV), and (C) 1-cyclohexyl-3-hexanoylurea (XLV) formed by the fission of the pyrimidine ring in I. Treatment of XXV with sodium or ammonium hydroxide resulted in the formation of oxazolidine -2, 4-dione derivatives.
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Capaurimine and Related Compounds. III. : Syntheses of dl-5, 6, 13, 13a-Tetrahydro-1, 2, 3, 10, 11-pentamethoxy-8H-dibenzo [a, g] quinolizine and dl-5, 6, 13, 13a-Tetrahydro-2, 3, 10, 11, 12-pentamethoxy-8H-dibenzo [a, g] quinolizine : Studies on the Syntheses of Heterocyclic Compounds. CCLXXXVI
TETSUJI KAMETANI, KAZUMI OHKUBO
1969 Volume 89 Issue 2 Pages
279-282
Published: February 25, 1969
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dl-1, 2, 3, 10, 11-Pentamethoxy-5, 6, 13, 13a-tetrahydro-8H-dibenzo [a, g]-quinolizine (IV) and dl-2, 3, 10, 11, 12-pentamethoxy-5, 6, 13, 13a-tetrahydro-8H-dibenzo [a, g] quinolizine (VII) were synthesized to examine if they were identical with O, O-dimethylcapaurimine but neither was the same and it was not possible to presume the structure of capaurimine from these compounds.
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NOBUO ISHIKAWA, SONOKO MURAMATSU, SHIZUE UEDA
1969 Volume 89 Issue 2 Pages
283-285
Published: February 25, 1969
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Monoiodohistidine was prepared by column chromatography on crystalline cellulose powder (Avicel). n-BuOH-AcOH-H
2O (4 : 1 : 2) was used as solvent-system.
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TSUNEHIRO KITAGAWA, TERUAKI OZASA, HYOZO TANIYAMA
1969 Volume 89 Issue 2 Pages
285-286
Published: February 25, 1969
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L-α, β-Diaminopropionic acid was obtained in 92% yield from L-aspartic acid by the Schmidt reaction using 30% fuming sulfuric acid and sodium azide.
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SHINTARO NOMURA
1969 Volume 89 Issue 2 Pages
287-289
Published: February 25, 1969
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Distribution of asperuloside and its related compounds in the aerial parts of 14 kinds of Genus Galium pants was examined using thin-layer chromatography. It was found that Asperuloside is present in all these plants and the presence of related compounds was observed in several plants. Asperuloside was isolated in crystalline form from all of the 14 tested plants.
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