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Volume 81, Issue 8
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Inhibition of Enzymic Acetylation of SulfanilamideKoji Oka, Kyoko Iwakura1961 Volume 81 Issue 8 Pages 1053-1056
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSAcetylation of sulfanilamide in the presence of enzyme extract of pigeon liver and coenzyme-A was tested with 47 kinds of compounds related to phenylethylacetic acid and the reaction was found to be inhibited. Relationship between chemical structure of these compounds and degree of activity was examined and following facts were found: (i) Activity tends to become stronger as the methylene chain between the phenyl and carboxyl becomes longer; (ii) there seemed to be no marked difference in activity due to stereoisomers, optical isomers, and geometric isomers; and (iii) inhibitory effect is generally stronger when the parent system has indone or naphthalene than when phenyl alone is present. The strongest inhibitory effect was found in 3-(1-indanyl)butyramide, m. p. 110.5°, among these 47 compounds.View full abstractDownload PDF (355K) -
Esters of N-Substituted α-Aminocyclohexaneacetic Acid, 2-(p-Halophenyl)glycine, and 2, 2-DiphenylglycineShigemi Kawahara, Hideyo Kawakami1961 Volume 81 Issue 8 Pages 1057-1062
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSA new synthetic method for alkyl esters of N-(2-diethylaminoethyl)-2-phenylglycine was described. A series of alkyl esters of α-(2-diethylaminoethyl)-2-(p-halophenyl)glycine and N-(2-dimethylaminoethyl)-2, 2-diphenylglycine were prepared and their antispasmodic activity was examined against barium chloride, histamine, and acetylcholine on isolated rabbit intestine and guinea pig ileum. Some of these esters showed two or three times greater spasmolytic action than papaverine.View full abstractDownload PDF (771K) -
Ester of N-Substituted 2-(p-Methoxyphenyl)glycine and 2-Phenylalanine, and Other Related Compounds of Ester of N-Substituted 2-PhenylglycineShigemi Kawahara, Hideyo Kawakami1961 Volume 81 Issue 8 Pages 1063-1067
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSA series of alkyl esters of N-(2-diethylaminoethyl)-2-p-methoxyphenyl)glycine and N-(2-diethylaminoethyl)-2-phenylalanine were synthesized by the condensation of α-monosubstituted amino acid ester and 2-chlorotriethylamine. Ethyl 2-phenyl-5-diethylaminovalerate and ethyl (2-diethylaminoethoxy)phenylacetate were prepared to compare their antispasmodic activity with that of the foregoing esters. Some of these esters showed 1-5 times greater spasmolytic activity than papaverine.View full abstractDownload PDF (635K) -
Relationship between Fluidity and AgglomerationEiichi Nakajima1961 Volume 81 Issue 8 Pages 1068-1075
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIn order to find the relationship between agglomeration and fluidity, sliding angle of glass beads in various liquids was measured and the result was considered with the presence or absence of agglomeration judged from sedimentation volume. Glass beads do not undergo agglomeration in hydrous polar liquids like water and hydrous alcohol, and show small sedimentation volume. Sliding angle in such a liquid is approximately constant irrespective of the viscosity, specific gravity, or surface tension of the liquid. On the other hand, glass beads undergo agglomeration in hydrous non-polar liquids like hydrous benzene at ordinary temperature (25°), has a large sedimentation volume, and a large sliding angle. The degree of agglomeration becomes smaller as the liquid temperature rises, even in hydrous non-polar solvent, and the phenomenon is accompanied by decrease in sliding angle. The degree of agglomeration can be predicted to a certain degree by the state of filling by tapping of a liquid and this value also agrees well with that of the sliding angle.
Sliding angle can be considered in two parts; the item that can be determined by the form of filling of particles and that determined from friction coefficient and adhesion force. Values for each of these items were determined for glass beads in air and adhesive force for the beads was calculated. Similar considerations were made for glass beads in liquid.View full abstractDownload PDF (909K) -
Synthesis of 3-Substituted Quinolizidine Derivatives. (1). Synthesis of 1-(3-Quinolizidinylmethyl)-3, 4-dihydro-6, 7-dimethoxyisoquinolineIchiro Matuo, Sadao Ohki1961 Volume 81 Issue 8 Pages 1075-1077
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe title compound (I) was synthesized in order to examine its uterus-contracting and antibacterial actions. Ethyl 3-quinolizidineacetate (VI) was obtained by oxidation of 3-allylquinolizidine (V) followed by esterification. The acid amide (VII) was obtained from (VI) and homoveratrylamine, and cyclization of (VII) with phosphoryl chloride afforded (I).View full abstractDownload PDF (435K) -
Synthesis of 3-Substituted Quinolizidine Derivatives. (2). Synthesis of Qulnolizidinylisoquinoline-type CompoundsIchiro Matuo1961 Volume 81 Issue 8 Pages 1078-1083
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe compounds (I) and (II) were prepared in order to examine uterus-contracting and antibacterial actions. Condensation of ethyl 4-oxo-3-quinolizidinecarboxylate (III) and homoveratrylamine or homopiperonylamine afforded the acid amide compounds (Va and Vb) which were submitted to Bischier-Napieralski cyclization to form 1-substituted 3, 4-dihydroisoquinoline compounds (VIa) and (VIb). Reduction of (VI) with lithium aluminium hydride finally gave (I) and (II). It was found that (III) used as the starting material contained over 80% of axial ethoxycarbonyl group and it was considered that (Va) and (Vb) obtained as only one kind of crystals has an axially bonded side chain.View full abstractDownload PDF (949K) -
Synthesis of 3-Substituted Quinolizidine Derivatives. (3). Synthesis of 3-Alkyl-, Aralkyl-, Aryloxyalkyl-, and Aminomethyl-quinolizidine, and 4-Oxo-3-quinolizidinecarboxamidesIchiro Matuo1961 Volume 81 Issue 8 Pages 1083-1089
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe present series of synthetic work was carried out in order to obtain compounds having uterus contracting action or analgesic-sedative action. Condensation of the potassium salt of ethyl 4-oxo-3-quinolizidinecarboxylate (I) and alkyl halide, followed by saponification and decarboxylation, afforded 3-substituted 4-quinolizidinone (III) whose reduction with lithium aluminium hydride gave 3-alkylquinolizidine (IV). Amide compounds (V) were obtained by condensation of (I) and amines, and reduction of (V) gave 3-aminomethylquinolizidines (VI). (VI) was also obtained by the condensation of 3-lupinine tosylate and amines.View full abstractDownload PDF (855K) -
Alkaloids of Nandina domestica f. shinananten HORTMasao Tomita, Motoko Sugamoto1961 Volume 81 Issue 8 Pages 1090-1093
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSAlkaloids were examined in Nandina domestica forma shinananten HORT. (Japanese name “Shina-nanten”) and alkaloids listed in Table I were identified. Leaves of several kinds of Japanese Nandina and Mahonia genera were examined and bases contained in them are also listed in Table I. It is taxonomically interesting that a large quantity of protopine was found in the leaves of Nandina domestica forma shinananten, a forma of the Nandina genus, while this alkaloid was not detected in the leaves of other Nandina and Mahonia genera.View full abstractDownload PDF (658K) -
1-Arylamino-1-deoxy-D-glucofuranuronamideYasuo Nakajima1961 Volume 81 Issue 8 Pages 1094-1099
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESS1-Deoxy-1-p-nitroanilino-D-glucofuranuronamide (IIIa) and 1-deoxy-1-anilino-D-glucofuranuronamide (IIIc) were prepared by amidation of 1-deoxy-1-p-nitroanilino-D-glucofuranuronolactona (IIa), and 1-anilino-1-deoxy-D-glucofuranuronolactone (IIc) with liquid ammonia. (IIIa) easily underwent conversion of the lactol ring by the presence of acid or base to form 1-deoxy-1-p-nitroanilino-D-glucopyranuronamide (IVa). This was examined by paper chromatography and its result revealed that (IIIa) converted to (VIa) through an intermediate with a cleaved lactol ring, i.e. conversion from furanose to pyranose.
The amide obtained by amidation of (IIa) was acetylated to 1-deoxy-1-p-nitroani-lino-tri-O-acetyl-D-glucuronamide (Va), p-nitroanilino group was liberated to form tri-O-acetyl-D-glucuronamide (VI), and further acetylated to tetra-O-acetyl-D-glucuronamide (VII). Fusion of (VII) with phenol and p-toluenesulfonic acid afforded (phenyl tri-O-acetyl-D-glucosid) uronamide (VIII). On the other hand, (phenyl 2, 3, 5-tri-O-acetyl-D-glucofuranosid) uronamide, obtained by acetylation of (phenyl D-glucofuranosid) uronamide, was found to have the same melting point, optical rotation, and infrared spectrum as (VIII). These facts proved that (IIIa), (Va), (VI), and (VIII) are furanose.View full abstractDownload PDF (888K) -
Extraction, Isolation, and PurificationYoshichika Odaka1961 Volume 81 Issue 8 Pages 1099-1102
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSDegreased cells of human-type tubercle bacilli (H37Rv strain) was extracted by the method of Goebel-Morgan and a polysaccharide fraction (II) of [α]D+150° was obtained. Acetylation of (II) by Smith method gave an acetylated compound (III) with a mean molecular weight of 14000-14500, and its deacetylation afforded a polysaccharide (IV). From the elemental analyses and molecular weight determination of (III) and (IV), and electrophoretic analysis of (IV), it was considered that (IV) is an electrophoretically approximately homogeneous polysaccharide with a mean molecular weight assumed at 8, 000-8, 400.View full abstractDownload PDF (599K) -
Sugar Components and Periodate OxidationYoshichika Odaka1961 Volume 81 Issue 8 Pages 1103-1105
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe polysaccharide (IV) obtained from human tubercle bacilli, as described in Part I of this series, would be composed of 48-50 glucose units and two arabinose units, considering the result of paper chromatography of its hydrolysate (Table I), quantitative and qualitative tests with carbazole-sulfuric acid and phenol-sulfuric acid reactions, and from the mean molecular weight of (IV). Periodate oxidation of (IV) showed that the ratio of consumption of periodate, to the amount of formic acid and formaldehyde produced was 61:5.8:1 in molar ratio. Bonding positions of constituent sugars in the polysaccharide which would satisfy the above molar ratio would be 1-2 or 1-4 in glucose and 1-, 2-, or 3-position in arabinose if it were a terminal group. The mode of configuration is assumed to be a straight chain with 2-6 branchings.View full abstractDownload PDF (416K) -
Constitution of the PolysaccharideYoshichika Odaka1961 Volume 81 Issue 8 Pages 1106-1108
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSMethylation of the acetylated polysaccharide (III), reported in Part I of this series, by the Haworth-Muskat method gave a methylated compound of m. p. 101-104° (decomp.), with 44.5%, of CH3O and mean molecular weight of 9800-10500. The constituting methylated sugars were estimated by paper chromatography of its hydrolysate (Table I) and quantitatively determined by the method of Schaefer and others (Table II). Approximate estimations were made for bonding position and mode of configuration of each componental sugar in (IV) (as shown in Fig. 2) from the position of absorption in the infrared spectrum of the acetylated compound (III) (Fig. 1), amount of formic acid formed by periodate oxidation of the original polysaccharide (IV) (cf. Part II), as well as from the result of present series of experiments.View full abstractDownload PDF (410K) -
Formation of Glucuronic Acid and Evolution of Carbon Dioxide in the Process of Acid Hydrolysis of the Oxidized StarchYuji Imai1961 Volume 81 Issue 8 Pages 1109-1115
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSStarch was oxidized with nitrogen dioxide and fuming nitric acid at a low temperature, hydrolyzed with acid, and the amount of glucuronic acid formed in the decomposition solution and the volume of carbon dioxide generated during decomposition were measured. Decarboxylation of oxidized starch is greater than that of glucuronic acid under the same condition and comparable to that of ascorbic acid and glucuronic acid osazone. Consequently, it would be difficult to consider that the oxidized starch is a glucuronic acid polymer, as was claimed by Kerr and others, and it was assumed that the molecule contained numerous labile carbonyl structures. Reduction of oxidized starch with sodium borohydride and subsequent acid hydrolysis resulted in marked decrease of carbon dioxide evolution and increase in the amount of uronic acid formed. Therefore, it was assumed that the carbonyl, in the majority, took the 2-oxo- or 3-oxo-glucuronic acid structure. The low yield of glucuronolactone by the acid hydrolysis of oxidized starch was concluded to be due to the formation of this oxo structure by secondary oxidation.View full abstractDownload PDF (988K) -
Periodate Oxidation of the Oxidized StarchYuji Imai1961 Volume 81 Issue 8 Pages 1115-1118
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSOxidized starch, obtained by oxidation with nitrogen dioxide system agents, was oxidized with sodium periodate, the aldehyde formed was reduced with sodium borohydride, and hydrolysis of the product with acid afforded tartaric acid as crystals. Separation of this acid as barium tartrate and oxidation of the filtrate with nitric acid afforded oxalic acid as crystals. Reduction of the oxidized starch with sodium borohydride, followed by oxidation with sodium periodate, and treatment of this product as above failed to afford any of the above crystalline products. It follows, therefore, that this oxidized starch has the 3-oxoglucuronic acid groupings in its molecule and the presence of 2-oxo structure was also confirmed.View full abstractDownload PDF (657K) -
Catalatic Action of Artificial Acidic Iron Solution. (1). Inhibitory Action of Sulfate IonMichio Suzuki1961 Volume 81 Issue 8 Pages 1119-1125
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSSulfate ion in the artificial springs containing iron* inhibits Catalatic action of iron (III) ion. The rate constant of catalytic decomposition of hydrogen peroxide is not only proportional to a 1.23 power of [Fe] and inversely proportional to (H+), but also inversely proportional to 1/2 power of [∑SO42-]. Further, it is evident that oxidation-reduction potential of the same spring is proportional to the negative logarithm of 1/2 power of [∑SO42-], from the analysis of the relation between [∑SO42-] and oxidation-reduction potential.
* Iron alum solution containing sodium sulfate in the sulfuric acid acidity; brown-yellowish colored aqueous solution of iron alum; supernatant liquid of hydrolyzed iron alum solution.View full abstractDownload PDF (778K) -
Catalatic Action of Artificial Acidic Iron Solution. (2). Promotory Action of Al3+, Mg, 2+ and Ca2+Michio Suzuki1961 Volume 81 Issue 8 Pages 1126-1129
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSArtificial mineral spring containing iron alum, with a large amount of aluminium or magnesium ion has stronger catalatic action than that which dose not contain these ions. In other words, aluminium and magnesium ions promote the catalatic action of iron ion. The mechanism of this accelerative action is thought to be the inhibition of effective concentration of sulfate ion by the presence of aluminium or magnesium ion, resulting in the increase of simple iron ion concentration.View full abstractDownload PDF (432K) -
On the Catalatic Action of Artificial Acidic Iron Solution. (3). Inhibitory Action of Halide Ion and Phosphate IonMichio Suzuki1961 Volume 81 Issue 8 Pages 1130-1135
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe catalatic action of artificial mineral spring containing sodium chloride and iron alum is weaker than that not containing sodium chloride, which shows that the catalatic action of iron is inhibited by chlorine ion as well. The degree of this inhibition is a function of sulfate ion concentration in the mineral water. There is no inhibitory action when the total concentration of sulfate ion is less than twice the total concentration of iron ion but the action appears when this becomes more than twice. The mechanism of this inhibition is thought to be the increase of effective concentration of sulfate ion by the presence of chlorine ion.
Inhibitory action of bromine ion is stronger than that of chlorine ion and is observed even when there is no inhibition by chlorine ion. Inhibition by iodine ion is 500 times greater than that of bromine ion. When liberation of iodine is observed on addition of hydrogen peroxide to mineral water, iodine promotes catalatic action. Presence of dihydrogen phosphate ion results in formation of a complex salt with ferric ion and this lowers the concentration of ferric ion, thereby inhibiting its catalatic action.View full abstractDownload PDF (724K) -
Catalatic Action of Artificial Acidic Iron Solution. (4). Promotory Action of Cu2+Michio Suzuki1961 Volume 81 Issue 8 Pages 1135-1140
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSCatalatic action of artificial mineral spring of acidic iron containing copper is in inverse proportion to the product of hydrogen ion concentration and 0.5 power of total sulfate concentration, as in the case of catalatic action of the iron spring not containing copper, and directly proportional to the total iron concentration. This fact shows that copper ion catalyzes simple iron ion but not iron sulfate ion. Therefore, artificial acid vitriol spring and acid iron alum spring, containing equal concentration of simple iron (III) concentration and copper ion, have the same degree of catalatic action. The accelerative effect of copper ion is independent of iron ion concentration and reaches. the maximum when copper ion concentration is 10-2M. At a greater concentration than this, there is no increased accelerative action of copper ion. The degree of catalatic activity becomes approximately 15 times greater, when copper ion concentration is 10-2M. Relationship between copper ion concentration and degree of acceleration is indicated by a primary sigmoid curve, p=[Cu2+]/[Cu2+]+1.8×10-6.View full abstractDownload PDF (670K) -
Catalatic Action of Natural Acidic Iron SpringMichio Suzuki1961 Volume 81 Issue 8 Pages 1141-1146
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSZaô spring (ageless spring), a few days after welling up, and Maka mineral spring, after precipitation and ageing had taken place, have catalatic action similar to that of artificial iron spring with similar chemical composition. Inhibitory substances are hydrogen ion, sulfate ion, and chlorine ion, and Cu2+ is accelerative. In both of these natural mineral springs, inhibitory action of chlorine ion is greater than the promoting action of Cu2+. Consequently, catalatic action of a natural spring may be weaker than that of the artificial spring with similar total iron, total sulfate, and hydrogen ion concentration. Mineral spring undergoes ageing as soon as it wells up and one of its causes may be the decreased concentration of cocatalyst. Catalatic action of natural springs is approximately in inverse proportion to the hydrogen ion concentration of the mineral water.View full abstractDownload PDF (777K) -
Yasuyuki Suzuki1961 Volume 81 Issue 8 Pages 1146-1150
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESS4-Pyridinesulfonic acid and 4-quinolinesulfonic acid were derived to the corresponding 4-amino-, 4-methylamino-, and 4-dimethylamino-pyridines and -quinolines in 60-90% yield by heating them with ammonium hydroxide, methylamine, in the presence of zinc chloride, in an autoclave at 150-160° for 20-24 hours. Similar reaction with hydrazine hydrate afforded 4-pyridyl- and 4-quinolyl-hydrazines in 70-80% yield. These hydrazines underwent condensation with acetone, benzaldehyde, pyruvic acid, and ethyl pyruvate to form 4-pyridyl- and 4-quinolyl-hydrazones, and reacted with acetylacetone to form 1-(4-pyridiyl and -quinolyl)-3, 5-dimethylpyrazole. While the reaction of 4-pyridylhydrazine with benzoyl chloride afforded a dibenzoyl compound, that with 4-quinolylhydrazine afforded a substance of C16H11N3.View full abstractDownload PDF (914K) -
Yasuyuki Suzuki1961 Volume 81 Issue 8 Pages 1151-1154
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSHeating of 2 moles of 4-chloropyridine 1-oxide or 4-bromoquinoline 1-oxide and 1 mole of sodium disulfide in aqueous solution results in formation of 4, 4′-thiodipyridine or 4, 4′-thiodiquinoline 1-oxide in 90% yield. Reaction of 1 mole each of the oxide and sodium disulfide gives 4-mercapto-pyridine or -quinoline 1-oxide in 90% yield, while the reaction with 1 mole of sodium thiosulfate affords 4, 4′-thiodipyridine or 4, 4′-thiodiquinoline 1-oxide in 80% yield.
Heating of 4-bromopyridine 1-oxide with potassium thiocyanate in ethanol does not result in the formation of a 4-thiocyanato compound but the same reaction with 3-nitro- or 3-bromopyridine 1-oxide gives 4-thiocyanato compound in 70% yield. 4-Bromoquinoline 1-oxide also undergoes this reaction to give 4-thiocyanatoquinoline 1-oxide in 81% yield. This 4-thiocyanato compound reacts with 2N sodium hydroxide or sodium carbonate when warmed and forms 4, 4′-thiodiquinoline 1, 1′-dioxide, which when warmed with sodium sulfide or reacted with 2N sodium hydroxide at room temperature forms 4-mercaptoquinoline 1-oxide. 4-Bromoquinoline 1-oxide reacts with potassium selenocyanide to form 4-selenocyanatoquinoline 1-oxide in 83.5% yield.View full abstractDownload PDF (691K) -
Effect of Bovine Harder's Gland Extracts on Serum Alkaline Phosphatase and Calcium in RabbitMotosuke Kikutani, Kazuko Hirose, Tsuyoshi Yamamoto1961 Volume 81 Issue 8 Pages 1154-1158
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSA substance affecting alkaline phosphatase activity of rabbit serum and serum calcium level was extracted and isolated from bovine Harder's gland. The gland was extracted with 0.01N ammonia water and fractionated into three fractions with ethanol. The gland was also extracted with 2% saline solution and fractionated into three fractions with ammonium sulfate. Examination of physiological activity of these fractions showed that fractions A-40, CS-3, and CS-5 increased alkaline phosphatase activity and decreased calcium level, while fractions A-44, A-80, and CS-10 lowered the phosphatase activity, and fractions A-80 and CS-10 effected transitory increase of serum calcium level with subsequent lowering. These results seem to partly prove the assumption that the Harder's gland was excreting a substance which increases or decreases alkaline phosphatase activity, as part of its physiological function. All of these fractions were considered to be a protein from the analysis of their total nitrogen and color reactions.View full abstractDownload PDF (705K) -
Flavonoid of the Leaves of Nelumbo nucifera GAERTN., Cosmos bipinnatus CAV., and Foeniculum vulgare MILLERTashichiro Nakaoki, Naokata Morita, Yoshikazu Nagata, Hiroshi Oguri1961 Volume 81 Issue 8 Pages 1158-1159
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSYellowish needles, m.p. 174-175°, [α]D26-21.1°, C27H28O18⋅6 1/2H2O, were isolated in respective yield of 0.1%, 0.01%, and 0.1% from the fresh leaves of Nelumbo nucifera GAERTN., Cosmos bipinnatus CAV., and Foeniculum vulgare MILLER. These three substances were all identical. This substance was named nelumboside. It colored dark greenish brown to ferric chloride and pink to magnesium or zinc and hydrochloric acid. Hydrolysis of nelumboside with 5% sulfuric acid gave 1 mole each of quercetin, glucose, and glucuronic acid and permethylation with diazomethane followed by hydrolysis afforded 5, 7, 3′, 4′-tetra-O-methylquercetin. It follows, therefore, that the sugar is bonded to the 3-position and nelumboside is quercetin 3-glucoglucuronide.View full abstractDownload PDF (370K) -
Studies on the Difference in the Spectra between α- and β-Anomers of Glucopyranuronic Acid DerivativesYoshihiro Nitta, Yasuo Nakajima, Masao Kuranari, Atsushi Momose, Junji ...1961 Volume 81 Issue 8 Pages 1160-1165
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSDifference in the infrared absorption spectra in the region of 1200-900cm-1 between α- and β-anomers of glucopyranuronic acid derivatives was examined. In the fully acetylated compounds, α-anomers exhibited characteristic absorption bands at around 1150 and 940cm-1, the C-O stretching vibration of the axial acetate group in C-1 appearing at around 1010cm-1, and that of the equatorial acetate group appearing at around 1040cm-1. The absorption bands at around 1080 and 910cm-1 are considered to be the asymmetric and symmetric stretching vibrations, respectively, of ether bonds in the pyranose.View full abstractDownload PDF (725K) -
Synthesis of 1-Deoxy-1-thioureido-β-D-glucopyranuronic Acid and its AmideYoshihiro Nitta, Masao Kuranari, Toshio Kondo1961 Volume 81 Issue 8 Pages 1166-1170
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSReaction of methyl 1-bromo-1-deoxy-2, 3, 4-tri-O-acetyl-α-D-glucopyranuronate (I) and 1-bromo-1-deoxy-2, 3, 4-tri-O-acetyl-α-D-glucopyranuronamide (VIII) with potassium thiocyanate in acetone afforded the corresponding thiocyanates, (II) and (IX), and their rearrangement by heating gave the corresponding isothiocyanates, (III) and (X). Treatment of (III) and (X) with ammonia in methanol resulted in the formation of identical 1-deoxy-1-thioureido-β-D-glucopyranuronamide (IV), while the reaction with ammonia in dioxane gave methyl 1-deoxy-1-thioureido-2, 3, 4-tri-O-acetyl-β-D-glucopyranuronate (V) and the corresponding uronamide (XI). Treatment of (V) with barium hydroxide afforded barium 1-deoxy-1-thioureido-β-D-glcopyranuronate (VII) and its reaction with hydrazine hydrate gave 1-deoxy-1-thioureido-β-D-glucopyranuronic acid hydrazide (VI). (IV) is much more stable than N-glucuronide of amines in general. Infrared absorption of thioureido group in (V) and (XI) appeared at around 1530-1550cm-1.View full abstractDownload PDF (692K) -
Synthesis and Antituberculosis Activity of 1-(3-Arylmethyleneaminothioureido)-1-deoxy-β-D-glucopyranuronic Acids and their AmidesYoshihiro Nitta, Masao Kuranari, Toshio Kondo1961 Volume 81 Issue 8 Pages 1171-1178
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSReaction of hydrazine with methyl 1-deoxy-1-isocyanato-2, 3, 4-tri-O-acetyl-β-D-glucopyranuronate (I) in dioxane affords methyl 1-(3-aminothioureido)-1-deoxy-2, 3, 4-tri-O-acetyl-β-D-glucopyranuronate (II) which undergoes condensation with aromatic aldehydes to form the corresponding thiosemicarbazone derivatives (III). Treatment of (III) with dilute alkali or ammonia in methanol gives 1-(3-arylmethyleneaminothioureido)-1-deoxy-β-D-glucopyranuronic acids (V) or -uronamides (VI). Treatment of (II) with ammonia in methanol affords 1-(3-aminothioureido)-1-deoxy-β-D-glucopyran-uronamide (IV) whose condensation with aldehyde also gives (VI). Infrared spectra of (II), (II′)-(VI) exhibit thioureido absorption at around 1530cm-1 and of (II) and (III) the asymmetric stretching vibration of C-O-C in the β-pyranose ring at around 1080cm-1. In vitro antituberculosis action of (V) and (VI) was not any better than the aromatic aldehyde thiosemicarbazones used as the control.View full abstractDownload PDF (832K) -
Synthesis of 1-(3-Arylthioureido)-1-deoxy-D-glucopyranuronic Acids or their AmidesMasao Kuranari1961 Volume 81 Issue 8 Pages 1179-1184
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSReaction of aromatic amines with methyl 1-deoxy-1-isocyanato-2, 3, 4-tri-O-acetyl-β-D-glucopyranuronate (I) affords methyl 1-(3-arylthioureido)-1-deoxy-2, 3, 4-tri-O-acetyl-β-D-glucopyranuronate (II). Application of dilute alkali or methanolic amonia to (II) resulted in the formation of 1-(3-arylthioureido)-1-deoxy-β-D-glucopyranuronic acid (III) and -uronamide (IV) respectively. As part of these compounds, sulfamerazine and isonicotinic acid hydrazide derivatives were also prepared. Infrared spectra of these compounds exhibited absorption bands of thioureido group at 1550-1520cm-1 and asymmetric stretching vibration of C-O-C in the β-pyranose ring at 1070cm-1.View full abstractDownload PDF (698K) -
Synthesis of 1-Alkoxythio-carbonylamino-1-deoxy-β-D-glucopyranuronamidesMasao Kuranari1961 Volume 81 Issue 8 Pages 1185-1188
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSReaction of aliphatic alcohols with methyl 1-deoxy-1-isothiocyanato-2, 3, 4-tri-O-acetyl-β-D-glucopyranuronate (I) afforded methyl 1-alkoxythiocarbonylamino-1-deoxy-2, 3, 4-tri-O-acetyl-β-D-glucopyranuronate (II) and its treatment with ammonia in methanol gave 1-alkoxythiocarbonylamino-1-deoxy-β-D-glucopyranuronamide (III). The absorption for -NHCS-linkage in the infrared spectrum of (II) appeared at 1510-1515cm-1 and in that of (III) at around 1550cm-1. The absorption for asymmetric stretching vibration of C-O-C in the β-pyranose ring appeared at 1070cm-1.View full abstractDownload PDF (577K) -
Synthesis and Infrared Absorption Spectra of 1-Azido-1-deoxy-β-D-glucopyranuronic Acid Derivatives and Methyl 1-Amino-1-deoxy-2, 3, 4-tri-O-acetyl-β-D-glucopyranuronateMasao Kuranari1961 Volume 81 Issue 8 Pages 1189-1194
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSApplication of sodium azide to methyl 1-bromo-1-deoxy-2, 3, 4-tri-O-acetyl-α-D-glucopyranuronate (I) and 1-bromo-1-deoxy-2, 3, 4-tri-O-acetyl-α-D-glucopyranuronamide (IV) in formamide afforded the corresponding azides (II and V). Treatment of these azides with ammonia in methanol gave the same 1-azido-1-deoxy-β-D-glucopyranuronamide (VI). Treatment of (II) with dilute aqueous solution of barium hydroxide gives 1-azido-1-deoxy-β-D-glucopyranuronic acid (III), while reduction of (II) with hydrogen bromide in glacial acetic acid solution gives methyl 1-amino-1-deoxy-2, 3, 4-tri-O-acetyl-β-D-glucopyranuronate hydrobromide (VII), which was derived to the free amine (VIII). Reaction of (VIII) with phenyl isothiocyanate or p-chlorophenyl isothiocyanate affords the corresponding thiourea derivatives (IX). The infrared spectrum of (II) exhibits absorptions for asymmetric stretching vibration of the azido group at 2140-2120cm-1, NH2 at 3405 and 3340cm-1, deformation vibration of NH2 at 1625cm-1, and deformation vibration of NH3+ at 1571 and 1510cm-1. Absorptions of asymmetric stretching vibration of the β-pyranose ring appeared at around 1080cm-1 and symmetric stretching vibration at around 900cm-1.View full abstractDownload PDF (709K) -
Synthesis of Methyl 1-(2-Arylmethylenehydrazono-4-oxo-3-thiazolidinyl)-1-deoxy-2, 3, 4-tri-O-acetyl-β-D-glucopyranuronates and Methyl 1-Deoxy-1-(2, 4-dioxo-3-thiazolidinyl)-2, 3, 4-tri-O-acetyl-βMasao Kuranari1961 Volume 81 Issue 8 Pages 1195-1201
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSCyclization between methyl 1-(3-arylmethyleneaminothioureido)-1-deoxy-2, 3, 4-tri-O-acetyl-D-glucopyranuronate (I) and ethyl chloroacetate in the presence of anhyd. sodium acetate afforded methyl 1-(2-arylmethylenehydrazono-4-oxo-3-thiazolidinyl)-1-deoxy-2, 3, 4-tri-O-acetyl-β-D-glucopyranuronate (II). Fusion of methyl 1-deoxy-1-ethoxythiocarbonylamino-2, 3, 4-tri-O-acetyl-D-glucopyranuronate (III) with chloroacetic acid afforded methyl 1-deoxy-1-(2, 4-dioxo-3-thiazolidinyl)-2, 3, 4-tri-O-acetyl-β-D-glucopyranuronate (VII), which was also obtained on refluxing silver salt (VI) of 2, 4-thiazolidine dione and methyl 1-bromo-1-deoxy-2, 3, 4-tri-O-acetyl-α-D-glucopyranuronate (V) in xylene. Refluxing of (III) and ethyl chloroacetate failed to effect cyclization and methyl 1-deoxy-1-(ethoxycarbonylmethylthio) carbonylamino-2, 3, 4-tri-O-acetyl-β-D-glucopyranuronate (IV) was obtained. The infrared spectrum of (II) showed absorption at 1625-1605cm-1, considered to be due to the conjugation system of -CH=N-N=C=, and the asymmetric stretching vibration of C-O-C in the β-pyranosyl ring appeared at around 1070cm-1.View full abstractDownload PDF (693K) -
Alkaloids of Nelumbo nucifera var. prolifera MIYOSHIMasao Tomita, Yasuo Watanabe, Hiroshi Furukawa1961 Volume 81 Issue 8 Pages 1202-1203
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSAlkaloids contained in the leaves and petiole of Nelumbo nucifera var. prolifera MIYOSHI (Japanese name “Myôren”) were examined. The main alkaloid was proved to be nornuciferine (III), a tertiary phenolic base, same as ordinary Japanese lotus (Nelumbo nucifera GAERTN.). A tertiary, non-phenolic bases, nuciferine (I) and roemerine (II), were isolated and identified from the leaves.View full abstractDownload PDF (281K) -
Yasuyuki Suzuki1961 Volume 81 Issue 8 Pages 1204-1206
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSHydrolysis of 2-substituted 4-cyanopyridine with hydrochloric acid, hydrobromic acid, or sodium hydroxide affords the corresponding 2-substituted isonicotinic acid in 60-80% yield. Substituents tested were methyl, chloro, bromo, hydroxyl, and 2, 6-dimethyl groups. Heating of these acids with ethanolic sulfuric acid or methanolic hydrochloric acid, application of thionyl chloride to form the acid chloride, and treatment with ethanol gives the ester. 4-Cyanopyridines and their N-oxides were derived to the corresponding thioisonicotinamides or their N-oxides in 65-85% yields by introduction of hydrogen sulfide in a solution or suspension of the substituted pyridines in pyridine, in the presence of triethylamine.View full abstractDownload PDF (452K) -
Yasuyuki Suzuki1961 Volume 81 Issue 8 Pages 1206-1207
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSDiazotization of 4-amino-alkylpyridine 1-oxide by application of sodium nitrite at a low temperature and treatment with potassium iodide afforded 4-iodo-alkylpyridine 1-oxide in 40-70% yield. A solution of these 1-oxides dissolved in chloroform, added with phosphoryl chloride under ice cooling, and allowed to stand at room temperature or warmed on a water bath afforded 4-iodo-alkylpyridine in 60-90% yield.View full abstractDownload PDF (262K) -
Pharmaceutical Application of Acid Amides as Solubilizing AgentMasayoshi Samejima1961 Volume 81 Issue 8 Pages 1208-1210
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSOver 20 kinds of a compound possessing excellent solubilization action were found among acid amides and 10 of these were selected, as listed in Table I, to examine the possibility of their use as a solubilization agent for pharmaceutics. Toxicity tests with mice indicated that the majority have very small toxicity, with the exception of a few, Solubilization effect of these substances against sparingly soluble pharmaceutics and food additives showed that they can be used for such practical purposes.View full abstractDownload PDF (425K) -
Ikuo Kikkawa1961 Volume 81 Issue 8 Pages 1210-1213
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe racemic compound of menisperine (I), the aporphine-type base contained in Menispermum dauricum DC., and the racemic compound of N-methyllaurotetanine (II), the aporphine-type base in Litsea cetrata BL., were synthesized earlier. It was shown at that time that the Pschorr reaction of phenanthrene cyclization had afforded, besides the objective aporphine-type bases and benzyltetrahydroisoquinolinetype base by further progress of deamination, a structurally unknown compound as colorless needles, m.p. 81-83°, during the synthesis of dl-menisperine (I) and that the same compound of colorless needles, m.p. 81-83°, and another structurally unknown compound had been obtained as colorless prims, m.p. 167-169°.
In the present series of work, examinations were made on these two kinds of structurally unknown substance and the compound of m.p. 81-83° was identified as 2-methyl-6, 7-dimethoxy-1, 2, 3, 4-tetrahydroisoquinoline (VI) and that of m.p. 167-169° as 5-benzyloxy-6-methoxy-1H-indazole (X).
This has shown that another example has been provided by this Pschorr reaction to the fact already pointed out by Tomita and Kitamura that, during the synthesis of aporphine-type bases by Pschorr's phenanthrene cyclization reaction, an abnormal side-reaction occurs by which the molecule is severed into two upper and lower fragments.View full abstractDownload PDF (452K) -
Yoshihiro Nitta, Hideyo Morita1961 Volume 81 Issue 8 Pages 1214-1215
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSA new derivative of D-glucuronic acid, methyl 1, 2-dideoxy-1, 2-dehydro-3, 4-di-O-acetylglucuronate, was quantitatively obtained by reduction of methyl 1-bromo-1-deoxy-2, 3, 4-tri-O-acetyl-α-D-glucopyranuronate with zinc dust and acetic acid.View full abstractDownload PDF (210K) -
Hyozo Taniyama, Bonpei Yasui1961 Volume 81 Issue 8 Pages 1216
Published: August 25, 1961
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSDownload PDF (170K)
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