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Volume 86, Issue 8
Displaying 1-17 of 17 articles from this issue
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Kaname Hamamoto, Norihide Maezono1966 Volume 86 Issue 8 Pages 639-648
Published: August 25, 1966
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSSynthesis of 16α- and 16β-methyl-17α, 21-dihydroxypregna-1, 4, 9(11)-triene-3, 20-dione 21-acetate, important intermediates for dexamethasone and betamethasone, from metagenin via 2β, 3β, 11α-trihydroxy-5β-pregn-16-en-20-one triacetate is described.View full abstractDownload PDF (1177K) -
Teisuke Okano, Shujiro Goya, Akira Takadate, Yoshiaki Ito1966 Volume 86 Issue 8 Pages 649-653
Published: August 25, 1966
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSFormamide and ethyl orthoformate-acetic anhydride mixture (1 : 1) have been compared for their cyclization properties to form various 4, 5-diamino-6-substituted-aminopyrimidines. It has been confirmed that the former yields 9-substituted-purines and the latter, 6-sub-stituted-aminopurines, indicating that the ring closure occurs between 5-and 6-amino groups in the former and between 4-and 5-amino groups in the latter. Identification of the reaction products was made through their ultraviolet spectral data.View full abstractDownload PDF (598K) -
Kazuyoshi Fujitani, Yoshiaki Aoyagi, Yukio Masaki1966 Volume 86 Issue 8 Pages 654-659
Published: August 25, 1966
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSdl-Armepavine (VIIIa) and dl-3'-bromo-4'-O-acetylarmepavine (IX) were synthesized and they were submitted to the Ullmann condensation in pyridine, in the presence of potassium carbonate, with copper powder or copper oxide powder as a catalyst, affording the title compound, 2-hydroxy-5, 4'-bis(2-methyl-6, 7-dimethoxy-1, 2, 3, 4-tetrahydroisoquinolin-1-yl-methyl)diphenyl ether (I). Examination of the infrared and NMR spectra of I indicated that I is a diastereoisomeric racemates having the same planar structure as natural dauri-cine (D, D).View full abstractDownload PDF (774K) -
Kazuyoshi Fujitani, Yukio Masaki1966 Volume 86 Issue 8 Pages 660-664
Published: August 25, 1966
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe title compound, 2, 7-bis(2-methyl-6, 7-dimethoxy-1, 2, 3, 4-tetrahydroisoquinolin-1-ylmethyl)-dibenzo-p-dioxin (IX), was synthesized by the Bischler Napieralski reaction of N, N'-bis(3, 4-dimethoxyphenethyl) dibenzo-p-dioxin-2, 7-diacetamide (VI). This compound was identified with the non-phenolic product from the Ullmann condensation of dl-armepavine and dl-3'-bromo-4'-O-acetylarmepavine. Cleavage reaction of IX with sodium in liquid ammonia afforded dauricine-type bases (X and XI).View full abstractDownload PDF (605K) -
Teruya Seki, Yoshiaki Watanabe, Makoto Aida1966 Volume 86 Issue 8 Pages 665-673
Published: August 25, 1966
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSWhen 2-(ω-hydroxyalkylthio)benzimidazole is heated, the most facile decomposition occurs when there are 2-methylene groups in the alkyl and 2-benzimidazolinone is formed. This decomposition becomes increasingly difficult with increase in the number of methylenes with the exception of four methylenes. Heating of 2-(2-aminoethylthio)benzimidazoles results in rearrangement and bis[2-(2-benzimidazolyl)aminoethyl]disulfide derivatives are formed. In either case, formation of a spirane compound as an intermediate was confirmed. Heating of 1-(2-diethylaminoethyl)-2-chlorobenzimidazole results in the formation of 1-ethyl-2, 3-dihydroimidazo[1, 2-α]benzimidazole. These pyrolysis and heat rearrangement reactions are all due to the electron-attracting nature of the carbon atom in the 2-position of the benzimidazole ring.View full abstractDownload PDF (1004K) -
Toshio Kawasaki, Itsuo Nishioka, Takeo Tsukamoto, Kunihide Mihashi1966 Volume 86 Issue 8 Pages 673-677
Published: August 25, 1966
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESS1) The rhizomes of Smilax China L., collected during November to December in Tokushima Prefecture, were found to contain diosgenin as the major sapogenin in the form of its glycosides. 2) Three glycosides, named smilax saponin A, B, and C, were detected and B was isolated in a pure state as colorless needles, m.p. 183∼186°(decomp.), [α]D -90°. 3) Smilax saponin B, consisting of diosgenin and three moles each of D-glucose and L-rhamnose, was hydrolysed with Takadiastase B to yield dioscin, indicating that it corresponds to a parent saponin of dioscin (diosgenin+glucose+2rhamnose). The minor saponins, A and C, were assumed also to be the parent saponins of dioscin having, respectively, four and two additional moles of monosaccharide.View full abstractDownload PDF (647K) -
Tsutomu Momose, Yosuke Ohkura, Toshihisa Imaizumi1966 Volume 86 Issue 8 Pages 678-682
Published: August 25, 1966
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSA micromethod for determination of urea nitrogen in blood with diacetyl monoximeglucuronolactone reagent was proposed using 0.02ml. of sample without using any special equipment. Simplicity of the procedure and stability of the color produced permit analysis of a large number of samples at one time. The outline of the procedure is as follows. To 0.58ml. of water in a centrifuge tube, 0.020ml. of blood or serum is add and mixed, 0.20ml. of sodium tungstate solution (5%) is then added and mixed. To this mixture 0.20ml. of alminum potassium sulfate solution (4.8%) is added, mixed well, and centrifuged. From this solution, 0.50ml. of the supernatant clear solution is pipetted into a test tube, 0.50ml. of diacetyl monoxime-glucuronolactone solution (1% each in 5% acetic acid) and 3.0ml. of phosphoric acid solution (550ml./L.) are added successively, and mixed. The tube is headed in a boiling water bath for 40 minutes, cooled in running water, and the absorbance is read at 475mμ against a reagent blank.View full abstractDownload PDF (568K) -
Mitsuji Furuhata, Teijiro Horiguchi, Masahide Kato1966 Volume 86 Issue 8 Pages 683-687
Published: August 25, 1966
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSSeasonal variations in the content of several components in essential oil of Wuzhang (Lindera umbellata TEUNB.) were studied by gas chromatography. The maximum content of essential oil in leaves was found in July, and that in branches in autumn.View full abstractDownload PDF (579K) -
Eisaku Hayashi, Hirohisa Saito1966 Volume 86 Issue 8 Pages 687-694
Published: August 25, 1966
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESS1) Formation of benzo[f]quinoxaline ring : Reaction was carried out between 1, 2-naphtha-lenediamine (I) and 2-hydroxyiminoacetophenone (II), 2-hydroxyiminopropiophenone (III), 1-hydroxyimino-1-phenylacetone (IV), 1-phenyl-1, 2-propanedione (V), pyruvic acid (VI), or chloroacetic acid (VII). 2-Phenylbenzo[f]quinoxaline (XII) (71%) and 3-phenylbenzo[f]quinoxaline (XIII) (25%) were obtained from I and II, and 2-methyl-3-phenylbenzo[f]quinoxaline (XVII) (73%) from I and III, but not 3-methyl-2-phenylbenzo[f]quinoxaline (XVIII). A viscous substance of unknown structure was formed from I and IV, with a minute amount of XVII. I and V afforded 24% of XVII and 18% of XVIII, while I and VI gave 79% of 2-methyl-3(4H)-benzo[f]quinoxalinone (XXI). 3-Methyl-2(1H)-benzo[f]quinoxalinone (XXII) was not identified. Reaction of I and VII afforded a mixture (78%) of 1, 2-dihydrobenzo[f]quinoxalinone (XXVII) and 3, 4-dihydro-2(H)benzo[f]quinoxalin3(4H)one (XXVII). 2) N-Oxidation of benzo[f]quinoxaline derivatives : N-Oxidation of benzo[f]quinoxaline (XXXIV) results in the formation of its 4-oxide (XXXIII) in 96% yield. This fact seems to suggest that the hydrogen in 10-position exerts a great steric hindrance on the oxidation of nitrogen in 1-position. N-Oxidation was also carried out on 2-methyl-(XIV), 3-methyl-(XXVI), 2-phenyl-(XII), 3-phenyl-(XIII), 2-methyl-3-phenyl-(XVII), 3-methyl-2-phenyl (XVIII), 2-chloro-(XXXII), 3, chloro-(XXXI), 3-chloro-2-methyl-(XXIII), and 3-ethoxy-benzo[f]quinoxaline (XXXVI), and benzo[f]quinoxaline-3-carbonitrile (XXXVII). One kind of an N-oxide was obtained from each of XIV, XXVI, XII, and XVIII, and these N-oxides were considered to be the 4-oxides (XXXVIII, XXXIX, XL, and XLI). One kind of an N-oxide was obtained also from XIII and, by consideration of the result of N-oxidation of quinoxaline derivatives, 10) this was also presumed to be the 4-oxide (XLII) of XIII. Two kinds of N-oxide were obtained from XVII and it is still unknown which is the 1-oxide (XLIII) and which the 4-oxide (XLIV). The corresponding N-oxides were not obtained from XXXII, XXXI, XXXIII, XXXVI, and XXXVII.View full abstractDownload PDF (934K) -
Tatsu Kawano, Masako Asakawa1966 Volume 86 Issue 8 Pages 695-699
Published: August 25, 1966
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSPrevious result on the determination of phenylanine in the urine of phenylketonuria by a microbiological method indicated marked inhibition by the presence of urea and, therefore, effect of urea on the calibration curve of phenylalanine was examined. It was thereby found that even as little as 1mg./ml. of urea affected the value of phenylalanine and that the growth of microorganisms was completely stopped by the presence of 15mg./ml.of urea. It was also found that aseptic filtration would be available as a method of disinfection as this hardly inhibited growth of the microorganisms. Since the use of aseptic filtration for microbiological assay is very inconvenient, an alternative method was devised by treating the samples containing urea with Amberlite CG-120 by which urea was found to be completely removed. A good result was obtained with recovery rate of phenylalanine coming to 100±4%. The recovery rate of phenylalanine is only 81% when urea was removed by acid decomposition. In the case of a sample containing conjugate-type amino acid, this amino acid is liberated by acid decomposition and this method cannot be used when free amino acid alone is to be determined. Therefore, the above resin treatment seems to be a convenient method in such a case.View full abstractDownload PDF (612K) -
Juichiro Shibasaki, Etsuko Nakamura, Yoshiki Sakamoto, Yukifumi Kuroka ...1966 Volume 86 Issue 8 Pages 699-707
Published: August 25, 1966
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSSince no report has appeared to date on the metabolism of N, N'-diaryl-N-alkylthiocarbanilide the metabolism of their typical derivative, N-methylthiocarbanilide, was studied. Examinations were made on the urinary metabolites in rabbits receiving the compound orally. Ether-soluble metabolites in the urine were examined by means of thin-layer chromatography, and unchanged N-methylthiocarbanilide, 4-hydroxy-N-methylthiocarbanilide, 4'-hydroxy-N-methylthiocarbanilide, 4, 4'-dihydroxy-N-methylthiocarbanilide, N-methylcarbanilide, 4-hydroxy-N-methylcarbanilide, 4'-hydroxy-N-methylcarbanilide, 4, 4'-dihydroxy-N-methyl-carbanilide, 4-hydroxythiocarbanilide, 4, 4'-dihydroxythiocarbanilide, and 4-hydroxyphenyliso-thiocyanate were detected, but their amount was very small. Therefore, in order to investigate the conjugates, the ether extract of the urine submitted to hydrolysis with β-glucuronidase was examined. By chromatography of the concentrated extract on silica gel column, a considerable amount of 4'-hydroxy-N-methylthiocarbanilide was isolated in crystalline form. These results suggest that the major metabolic pathway of N-methylthiocarbanilide in rabbits is hydroxylation in the 4'-position followed by conjugation with glucuronic acid, and, as a minor reaction, hydroxylation in the 4-position, N-demethylation, desulfurization, and cleavage of C-N linkage take place.View full abstractDownload PDF (965K) -
Shokei Fujisawa, Mitsuo Kawamura, Shoko Kawabata1966 Volume 86 Issue 8 Pages 708-713
Published: August 25, 1966
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSPhotodecomposition of 10-(2-dialkylaminopropyl)phenothiazines was carried out in acid solution. In contrast to phenothiazines having a 3-dialkylaminopropyl group in 10-position described previously, the main reaction in these compounds was found to be the cleavage of the side chain in the 10-position. As a result of photodecomposition, phenothiazines, 10-methylphenothiazines, and phenothiazones precipitated, and formaldehyde, acetaldehyde, and dimethylamine were formed as the product of decomposition of the side chain. Sulfoxides hardly formed. The mechanism of photodecomposition was found to be affected by the amount of air. Among the compounds examined, N, N-dimethyl-10-(2-dimethylaminopropyl)phenothiazine-2-sulfonamide was the most easily decomposed and formed complicated products.View full abstractDownload PDF (848K) -
Shokei Fujisawa, Mitsuo Kawamura, Shoko Kawabata1966 Volume 86 Issue 8 Pages 714-719
Published: August 25, 1966
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSPhotodecomposition was carried out on several kinds of phenothiazine derivatives, possessing sulfamoyl, nitrile, or methoxyl group in the 2-position, in acid solution, and comparative examination was made on the effect of the side chain in the 10-position on decomposition of sulfamoyl group, sulfoxidation, and dimerization. In any of these decomposition reactions, 10-(3-dialkylamino-1-propyl)phenothiazines are more easily photodecomposed thae 10-(2-dialkylaminoethyl)phenothiazines. Reaction rate is dependent on the pH, and the decomposition in general is faster at lower pH.View full abstractDownload PDF (748K) -
Ichizo Okabayashi, Tomie Oe(Mitsui)1966 Volume 86 Issue 8 Pages 720-726
Published: August 25, 1966
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESS1-Chloroxanthen-9-ol (IIIa) was prepared by the reduction of 1-chloroxanthen-9-one (IIa) with sodium amalgam and ethanol. IIIa was condensed with malonic acid to 1-chloroxanthene-9-malonic acid (IVa), and the acid was decarboxylated to 1-chloroxanthene-9-acetic acid (Va). Cyclization of l-(m-chlorophenoxy)benzoic acid (XI) afforded a mixture (IIa') of IIa and 3-chloroxanthen-9-one, and IIa was not isolated. Therefore, IIa was prepared from 1-amino-xanthen-9-one. (Ia). 2-, 3-, and 4-Chloroxanthene-9-acetic acids (Vb-d) were prepared and their alkamine ester hydrochlorides were obtained. The anti-acetylcholine, anti-barium chloride, and anti-histamine activities of Va∼d these ester hydrochlorides were examined and it was found that the introduction of chlorine into the xanthene ring of the alkamine ester hydrochlorides of xanthene-9-acetic acid, especially into the 2-or 3-position resulted in the weakening of these activities.View full abstractDownload PDF (773K) -
Akira Minato, Taketo Ogiso, Hideo Hoshino1966 Volume 86 Issue 8 Pages 726-731
Published: August 25, 1966
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe effects of amino acid chelate on succinoxidase activity were studied and the inhibitory action of cupric ion on oxidation of succinate by mouse liver homogenate was compared with that of amino acid chelates of copper. Of nine amino acid chelates examined, methionine, lysine, and especially histidine chelate showed marked inhibitory effect on succinoxidase than cupric ion alone (Fig.1 and Table II). In these investigations, the effect of addition of various metals was examined and it was shown that the addition of Mn2+ as well as Ca2+ and Al2+ to succinoxidase system accelerated the rate of oxygen uptake (Table III). With increasing concentration of Mn2+, increase of succinate oxidation was observed but inhibition occurred with further increase of Mn2+ (10-3M) (Fig.2). Addition of Mn2+ and histidine markedly accelerated the aerobic oxidation of succinate and it was found that the effect of this acceleration was not due to chelate formation (Fig.3). Oxidation of succinate in succinoxidase system was strongly inhibited by oxalacetic acid, but the activity was restored by the addition of Mn2+ and histidine (Fig.4).View full abstractDownload PDF (741K) -
Naokata Morita, Mineo Shimizu1966 Volume 86 Issue 8 Pages 732-734
Published: August 25, 1966
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSDried cut root bark of Zanthoxylum ailanthoides SIEB. et Zucc. was extracted with ether and then with methanol. From the ether extract, xanthyletin was obtained and hesperidin from the methanol-extract.View full abstractDownload PDF (450K) -
Toshio Anmo, Hidehumi Hayashi, Shozo Kouchiwa, Takeshi Nagayoshi1966 Volume 86 Issue 8 Pages 735-737
Published: August 25, 1966
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSTwelve compounds (listed in Table I) were derived from 5-methylsulfonyl-2-furaldehyde, prepared by the introduction of an electron-attracting group like methylsulfonyl in place of nitro group in 5-nitrofurfural. Minimum inhibitory concentration of these derivatives in vitro against fungi and bacteria is listed in Table II.View full abstractDownload PDF (445K)
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