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Volume 85, Issue 6
Displaying 1-23 of 23 articles from this issue
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Yasuko Hikino1965 Volume 85 Issue 6 Pages 477-480
Published: June 25, 1965
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESS(+)-Sabinene was oxidised with peracetic acid to give three crystalline products, A, B, and C. B and A were found to be (+)-p-menthane-1β, 2α, 4α-triol (VIII) and its racemate, respectively. Evidence was provided to support structure XIII for C. A and B correspond to the peracetic acid oxidation products of sabinene obtained by Henderson for which the tentative formula (II) was suggested.View full abstractDownload PDF (634K) -
Syntheses of Hydroxyfluoran DerivativesItsuo Mori1965 Volume 85 Issue 6 Pages 481-485
Published: June 25, 1965
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSSymmetric di- and tetrahydroxyfluoran and nonsymmetric mono-, di-, and tri-hydroxyfluorans were prepared by the method reported in literature. Newly synthesized nonsymmetric chlorine derivatives were 2′-monochloro, 4′-monochloro, and 2′, 4′-dichloro derivatives of 3′-monohydroxy-, 3′, 5′- and 3′, 7′-dihydroxy-, and 3′, 5′, 6′-, 3′, 6′, 7′-, and 3, 6, 8-trihydroxy-fluorans (nos. 13-33). These were prepared by the condensation of o-(2, 4-dihydroxybenzoyl) benzoic acid (I), o-(3-chloro-2, 4-dihydroxybenzoyl) benzoic acid (III), o-(5-chloro-2, 4-dihydroxybenzoyl) benzoic acid (II), or o-(3, 5-dichloro-2, 4-dihydroxybenzoyl) benzoic acid (IV) with phenolic compounds (cf. Chart 1). These hydroxyfluorans had a faint fluorescence and showed a distinct coloration in the acid and alkaline range. Solubility was the greatest in 1′, 3′, 6′, 8′-tetrahydroxyfluoran derivatives, followed by 2′, 3′, 6′, 7′-tetrahydroxyfluorans, and the solubility of dihydroxyfluoran derivatives was similar to that of fluorescein.View full abstractDownload PDF (567K) -
Coloring of Hydroxyfluorans Derivative's Metal Ion ComplexItsuo Mori1965 Volume 85 Issue 6 Pages 486-495
Published: June 25, 1965
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSRelationship between color and pH range was examined in about 49 kinds of hydroxyfluorans (including 7 symmetric, 6 nonsymmetric, 15 chlorinated nonsymmetric, 11 chlorinated symmetric, and 10 hydroxyfluoran complexones) (cf. Table I). The color is generally light in 1′, 3′, 6′, 8′-tetrahydroxyfluoran derivatives and deep in 2′, 3′, 6′, 7′- and 3′, 4′, 5′, 6′-tetrahydroxyfluorans. Chlorinated 3′, 6′, 7′- and 3′, 5′, 6′-trihydroxyfluorans, and aminoacetic acid and iminodiacetic acid complexones of tetrahydroxyfluorans also showed fairly deep coloration.
Coloration reaction of 18 kinds of tetrahydroxyfluoran derivatives with various metal ions was examined (cf. Table II). Coloration was found to occur with Bi3+, Zr4+, Th3+, and Ce4+, in the acid range, with Hg2+, Pb2+, Cd2+, Co2+, Ni2+, and Cu2+ in neutral to weakly acid range, and with Fe3+, Al3+, Zn2+, Mg2+, Ba2+, Sr2+, and Ca2+ in neutral to weakly alkaline range. Detection limit of these metals was examined with Bi3+ and Hg2+ by gross observation in a test tube, and on filter paper and spot plate.View full abstractDownload PDF (1200K) -
On the Properties of α- and β-Crystallin in Lens ProteinMasayuki Nakagaki, Naofumi Koga, Shuzo Iwata1965 Volume 85 Issue 6 Pages 496-501
Published: June 25, 1965
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIn order to obtain pure samples of α- and β-crystallin from bovine lens cortex, α-crystallin was purified by repeated precipitation at pH 5.0 with acetic acid, and β-crystallin by salting-out with ammonium sulfate from the supernatant after α-crystallin was discarded.
The properties of the crystallins were studied by chromatography by DEAE-cellulose, electrophoresis, and ultracenrifugation. On the chromatographic pattern eluted by phosphate buffer of pH 6.8, α-crystallin showed the main peak at 0.4M eluate, while β-crystallin showed the main peak at 0.015M eluate. The electrophoresis diagrams were found to be single peaks for both crystallins. The sedimentation coefficient of the main peak was 1.37 for α-crystallin and 5.2 for β-crystallin. These data suggest that the molecular weight of α-crystallin is greater than that of β-crystallin. Both α- and β-crystallin seemed to change their properties during column chromatography.View full abstractDownload PDF (892K) -
Synthesis and Pharmacological Action of Quinazolone DerivativesShoji Toyoshima, Katsutoshi Shimada, Sachiyuki Hamano, Toshiharu Ogo1965 Volume 85 Issue 6 Pages 502-506
Published: June 25, 1965
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSFusion of anthranilamide (VII) with urea or thiourea respectively gave 3-aryl-2, 4-(1H, 3H)-quinazolinedione (I) and 3-aryl-2-thio-2, 4 (1H, 3H)-quinazolinedione (II). 3-Aryl-2, 3-dihydro-4(1H)-quinazolinone (III) was obtained from VII and formaldehyde (cf. Chart 1 and Table I). Central-inhibiting action of the 25 compounds thus obtained was tested and those exhibiting a comparatively strong activity are listed in Tables II, III, and IV.View full abstractDownload PDF (692K) -
The Reaction of 2, 3-Disubstituted-4 (3H)-quinazolinone with Peracetic AcidShoji Toyoshima, Sachiyuki Hamano, Katsutoshi Shimada1965 Volume 85 Issue 6 Pages 507-510
Published: June 25, 1965
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSOxidation of 2-methyl-3-aryl-4 (1H)-quinazolinone with peracetic acid afforded aryl o-nitrobenzoate and a new compound assumed to be 2-methyl-3-aryl-4 (3H)-quinazolinone 1-oxide. Measurement of the ultraviolet and infrared spectra, and catalytic reduction and oxidation reactions of this new compound showed that it is a normal nitron-type compound, i.e. 1-oxide.View full abstractDownload PDF (513K) -
Identification of Sugar Component and Isolation of 2, 3, 6-Tri-O-methyl-D-galactose from the Methylated SubstanceMasashi Tomoda, Kimie Murayama1965 Volume 85 Issue 6 Pages 511-514
Published: June 25, 1965
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSPolysaccharides were extracted from the seeds of Lupinus luteus and constituent sugars were examined. Of these sugars, 60% was D-galactose, and other sugars were L-arabinose, D-xylose, L-rhamnose, and D-galacturonic acid. A fraction rich in galactose was separated from the polysaccharide and the majority of the methylated monosaccharides obtained after methylation followed by hydrolysis was identified as 2, 3, 6-tri-O-methyl-D-galactose. Consequently, fundamental structure of this polysaccharide is a 1→4 bonded chain of D-galactose.View full abstractDownload PDF (594K) -
Syntheses of Various Esters from Aliphatic Carboxylic Acid HydrazidesTetsuji Kametani, Osamu Umezawa1965 Volume 85 Issue 6 Pages 514-517
Published: June 25, 1965
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSFollowing previous work on the formation of corresponding esters by the reaction of various hydrazides with chloral or bromal in the presence of various alcohols, dehydrazination of 12 kinds of aliphatic carboxylic acids was examined. The compounds examined were propionic, butyric, valeric, hexanoic, heptanoic, octanoic, nonanoic, and decanoic acid hydrazides, dibasic malonic, succinic, and glutaric acid hydrazides, and phenoxyacetic acid hydrazide. The anticipated esters were successfully obtained. It was also found that when halogen was detected in the product even after purification through distillation, alumina chromatography removed the occluded chloral hydrate.View full abstractDownload PDF (565K) -
The Reaction of Heterocyclic Carboxylic Acid Hydrazides with ChloralTetsuji Kametani, Osamu Umezawa, Haruhiko Yagi, Setsu Asagi1965 Volume 85 Issue 6 Pages 518-520
Published: June 25, 1965
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSFollowing derivation of aliphatic carboxylic acid hydrazides to esters, the same reaction was carried out on heterocyclic carboxylic acid hydrazides, using 2-furoic acid, 2-thiophenecarboxylic acid, and three kinds of pyridinecarboxylic acid hydrazides, and the anticipated esters were also obtained. The intermediates in this reaction, 1-(2-furoyl)- and 1-(2-thenoyl)-2-(2, 2, 2-trichloroethylidene) hydrazine (III and VI), were found to form the esters when heated in ethanol. This fact indicated that the acid hydrazides converted to their esters through III and VI.View full abstractDownload PDF (395K) -
On the Color Formation of L-Ascorbic Acid Solution. (6)Shoji Otani1965 Volume 85 Issue 6 Pages 521-530
Published: June 25, 1965
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe mechanism of the color formation of ascorbic acid, especially the role of furfural in it, and its decomposition products, were studied. Quantitative analysis of the color was done by absorption at the dominant wave length of the colored solution, saturated with sodium hydrogen carbonate. It was assumed that furfural was formed by the hydrolysis of ascorbic acid, since it was slightly formed from dehydroascorbic acid or 2, 3-diketogulonic acid, the decomposition products from oxidation of ascorbic acid. The amount of furfural produced was very small when ascorbic acid solution was heated at acid or neutral range, compared to the decomposition of ascorbic acid under anaerobic condition, and furfural was very stable in water. Color formation through furfural was very small in theoretical value compared to the assayed value. It was found that furfural was not an important factor in the color formation of ascorbic acid. It was assumed that the color formed by oxidation of ascorbic acid through dehydroascorbic acid, and hydrolysis was not important for color formation. From these observations, it is concluded that the prevention of oxidative reaction is necessary to avoid color change of ascorbic acid solution. For this purpose, addition of antioxidants and nitrogen filling must be carried out.View full abstractDownload PDF (1301K) -
Tadashi Suyama, Seizo Kanao1965 Volume 85 Issue 6 Pages 531-533
Published: June 25, 1965
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSDecarboxylation of amino acids was carried out with tetralin and cyclohexanol. 1-Amino-2-methylbutane obtained from L-isoleucine was found to be the DL-compound by the measurement of optical rotatory dispersion. This reaction of L- and D-threonine respectively afforded (-)-and (+)-1-amino-2-propanol, which formed dioxalate of m.p. 141°, [α]D to +22°. 2-Amino-1-ethanol was obtained from L-serine. The yield of these compounds was around 80%. DL-Tryptophan gave tryptamine hydrochloride, m.p. 249-250° (acetate, m.p. 136°, yield 65%), L-proline gave pyrrolldine (picrate, yield 36%), L-lysine gave cadaverine dihydrochloride, m.p. 257° (36%), and L-hydroxyproline gave L-3-hydroxy-pyrrolidine (hydrochloride yield 32%), which was identified as 1, 1-dimethiodide of m.p. 230°, [α]D24 -8.02°.View full abstractDownload PDF (483K) -
Synthesis of 2-Ethyl-1-naphthoic AcidZen-ichi Horii, Masanori Sakamoto, Takefumi Momose, Yasumitsu Tamura1965 Volume 85 Issue 6 Pages 534-538
Published: June 25, 1965
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSAs a preliminary experiment for the synthesis of 2-ethyl-5-hydroxy-1-naphthoic acid (VI), which is a promising intermediate for the synthesis of η-pyrromycinone (I), preparation of 2-ethyl-1-naphthoic acid (VII) was investigated. Michael condensation of benzyl cyanide and ethyl 2-pentenoate with one molar equivalent of sodium ethoxide in ethanol gave the cyano-ester (X) in 48% yield. Hydrolysis of X gave a 68% yield of the phenylglutaric acid (XI), which was cyclized with polyphosphoric acid, followed by esterification of the resulting diastereomeric mixture (XIImix.) of the tetralone-acid with diazomethane, to give the tetralone-ester (XIIImix.) in 57% yield. Sodium borohydride reduction, followed by dehydration and simultaneous dehydration with sulfur, converted XIIImix. into VII in 25% yield.
The trans isomer (XIIa) and cis isomer (XIIb) were separated from XIImix. by using difference in their solubilities towards ether, and converted by treatment with diazomethane into trans (XIIIa) and cis isomers (XIIIb), respectively. Their stereochemical assignments were made by the following isomerization behaviors of XIIIa and XIIIb. Hydrolysis of XIIIa or XIIIb with boiling 20% potassium hydroxide solution and subsequent esterification with diazomethane gave a mixture of XIIIa and XIIIb, whose ratio was, determined by the base-line method on the infrared absorption band at 1117cm-1; it was found that XIIIa is a more stable isomer than XIIIb.View full abstractDownload PDF (843K) -
The Mechanism of Action of Diphenylaminoethylguanidine as a Skeletal Muscle RelaxantHikaru Ozawa, Masaaki Takeda1965 Volume 85 Issue 6 Pages 539-543
Published: June 25, 1965
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe mode and site of muscle relaxing action of diphenylaminoethylguanidine (I) were investigated by observing (1) influence of stimulus frequency, (2) effect on muscle membrane potential, (3) interaction with other muscle relaxants and their antagonists, and (4) inhibitory effect on acetylcholine (ACh)-induced contracture.
Diphenylaminoethylguanidine (I) blocked neuromuscular transmission in the sciaticsartorius preparation of a frog, which might be due to the reduction of amplitude of the end-plate potential. This block was recovered by potassium ion, guanidine, and tetanic stimulation, but deepened by neostigmine, succinylcholine, and d-tubocurarine. The mode of neuromuscular blocking action of I was more similar to that of procaine than to those of succinylcholine or d-tubocurarine. On the other hand, I inhibited the contracture of frog rectus caused by ACh. It is suggested that one of the possible mechanisms of I is the inhibition of the effect of ACh in postjunctional region. However presynaptic inhibition of I could not be ruled out.View full abstractDownload PDF (779K) -
Ikuo Matsumoto1965 Volume 85 Issue 6 Pages 544-546
Published: June 25, 1965
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSReplacement of phenolic hydroxyl groups by chlorine was readily effected with thionyl chloride in the presence of a small amount of dimethylformamide when the hydroxyl groups were highly acidic. Simplicity of isolation process and short reaction time make this procedure attractive for the preparation of picryl chloride, 2, 4-dichloro-1, 3, 5-trinitrobenzene, and analogous products. Combination of the two reagents was successfully applied to some nitrogen heterocycles such as 2, 3-quinoxalinediol, while most of the pyrimidinols examined gave intractable products under similar conditions.View full abstractDownload PDF (501K) -
Toyosaku Sasaki1965 Volume 85 Issue 6 Pages 547-550
Published: June 25, 1965
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSExaminations were made on the components of the bark of Juglans regia L. var. orientalis KITAMURA and glucose, meso-inositol, quercetin, and quercitrin (quercetin 3-rhamnoside) were detected. Besides these, l-flavanone was isolated and this was found to be l-sakuranetin, m.p. 151°, [α]D32 -6.24° (EtOH). This gives dark brownish red color with ferric chloride, cherry red with magnesium-hydrochloric acid, and forms an acetate, C16H12O5(COCH3)2, m.p. 104-106°, by acetylation with acetic anhydride and pyridine. Iodine oxidation gave genkwanin (4, 5-dihydroxy-7-methoxyflavone), m.p. 282°.View full abstractDownload PDF (775K) -
Keijiro Takagi, Issei Takayanagi, Hiroshi Imamura1965 Volume 85 Issue 6 Pages 550-552
Published: June 25, 1965
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSAppearance of physical dependence of 1-[2-{α-(p-chlorophenyl) benzyloxy} ethyl] piperidine (HT-11) was tested on rats, comparing with that of morphine as a control. All the chemicals used were given to test animals as a subcutaneous injection. Decrease in body weight due to physical dependence was observed, if the administration was discontinued or otherwise when either Levallorphan or HT-11 was administered instead of morphine after a repeated administration of morphine (100mg./kg./day) to rats twice a day. No decrease in body weight was observed in rats treated previously with repeated administration of HT-11 (20 or 40mg./kg., once a day), when the administration was stopped or Levallorphan was given instead of HT-11. These results suggest that HT-11 is not a narcotic antitussive drug.View full abstractDownload PDF (550K) -
Masaiti Yasue, Motoiti Itaya, Hideyuki Oshima, Syoichi Funahashi1965 Volume 85 Issue 6 Pages 553-556
Published: June 25, 1965
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe leaves of Vaccinium bracteatum THUNB. were extracted with methanol and the extract was treated as shown in Chart 1. The substances isolated were hentriacontane, friedelin, epifriedelinol, quercetin, orientin (suggested), homo-orientin, p-hydroxycinnamic acid, and myo-inositol.View full abstractDownload PDF (602K) -
Alkaloids of Formosan Stephania japonica MIERS. (4). Synthesis of DL-N-Methyl-O, O-diethylisococlaurine and the Structure of StepholineMasao Tomita, Toshiro Ibuka1965 Volume 85 Issue 6 Pages 557-560
Published: June 25, 1965
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSDL-1-(p-Ethoxybenzyl)-2-methyl-6-ethoxy-7-methoxy-1, 2, 3, 4-tetrahydroisozuinoline (V) was synthesized and its infrared spectrum (in chloroform) was compared with that of L-N-methyl-O, O-diethylcoclaurine (IV). There was hardly any difference in their absorptions (Fig. 1) but their NMR spectra were clearly different (Fig. 2). The NMR spectrum of the non-phenolic base, obtained by the cleavage of O, O-diethylstepholine with metallic sodium in liquid ammonia, indicated that this base is D-N-methyl-O, O-diethylcoclaurine and not D-N-methyl-O, O-diethylisococlaurine.
Consequently, re-examinations were made on stepholine (I) and obamegine (II), and the infrared and NMR spectra of their pure compounds were found to be identical. It was also found that the difference in the melting point of stepholine (m.p. 171-173°) and of obamegine (m.p. 135-136°) was due to the addition of benzene or not. The pure compounds of these two substances melted at 171-173°, and stepholine and obamegine were found to be identical substances. Consequently, the name stepholine will henceforth be discarded.View full abstractDownload PDF (481K) -
Syntheses of Chlorohydroxyfluoran Derivatives and Hydroxyfluoran ComplexonesItsuo Mori1965 Volume 85 Issue 6 Pages 561-564
Published: June 25, 1965
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSDibenzofluoran and asymmetric 6′-hydroxybenzofluoran were prepared by the method reported in past literature. Other unknown compounds prepared were four asymmetric chlorinated hydroxybenzofluorans and three asymmetric chlorinated hydroxybenzofluorans. Condensation of o-(5-chloro-2, 4-dihydroxybenzoyl) benzoic acid (II) and α- or β-naphthol, and that of o-(3, 5-dichloro-2, 4-dihydroxybenzoyl) benzoic acid (III) with α- or β-naphthol respectively afforded 6′-hydroxy-7′-chloro-2′, 3′-benzofluoran or 6′-hydroxy-7′-chloro-3′, 4′-benzofluoran, and 5′, 7′-dichloro-6′-hydroxy-2′, 3′-benzofluoran or 5′, 7′-dichloro-6′-hydroxy-3′, 4′-benzofluoran. Direct dichlorination of tetrahydroxyfluoran gave chlorohydroxybenzofluoran.
Newly synthesized N-carboxymethylaminomethyl derivatives of 3′, 5′, 6′-, 3′, 6′, 7′-, and 3′, 6′, 8′-trihydroxy-, and 2′, 3′, 6′, 7′-, 3′, 4′, 5′, 6′-, and 1′, 3′, 6′, 8′-tetrahydroxyfluoraniminodiacetic acid, and 1′, 3′, 6′, 8′-, 2′, 3′, 6′, 7′-, and 3′, 4′, 5′, 6′-tetrahydroxyfluoranaminoacetic acid complexone compounds, which were obtained by the condensation of hydroxyfluoran and aminoacetic acid, or that of hydroxyfluoran with iminodiacetic acid and formaldehyde, following the synthetic method for 3′, 6′-dihydroxyfluoraniminodiacetic acid complexone.View full abstractDownload PDF (496K) -
1965 Volume 85 Issue 6 Pages e1a
Published: 1965
Released on J-STAGE: February 19, 2010
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1965 Volume 85 Issue 6 Pages e1b
Published: 1965
Released on J-STAGE: February 19, 2010
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1965 Volume 85 Issue 6 Pages e1c
Published: 1965
Released on J-STAGE: February 19, 2010
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1965 Volume 85 Issue 6 Pages e1d
Published: 1965
Released on J-STAGE: February 19, 2010
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