Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Volume 24, Issue 2
Displaying 1-33 of 33 articles from this issue
  • MICHIYA KIMURA, TOSHIAKI MIURA
    1976 Volume 24 Issue 2 Pages 181-185
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    As in the case of 3-methoxy-17α-methylestra-1, 3, 5 (10)-trien-17β-ol (IV), the maximum absorption at 372 nm was immediately shown when 3-methoxyestra-1, 3, 5 (10)-trien-17α-ol (V), 3-methoxyestra-1, 3, 5 (10), 16-tetraene (VI), or 3-methoxy-17β-methyl-18-norestra-1, 3, 5 (10), 13-tetraene (VII) was dissolved in 97.2% H2SO4. Colorless leaflets, mp 122-124°, were obtained in 90% yield when IV came into contact with the same acid at room temperature for 20 min. Ultraviolet, mass and nuclear magnetic resonance spectral data indicated this product to be 3-methoxy-17, 17-dimethyl-13ξ, 14ξ-18-norestra-1, 3, 5 (10), 8-tetraene (VIIIb). Similarly, the same reaction of V, VI, or VII gave 3-methoxy-17β-methyl-13ξ, 14ξ-18-norestra-1, 3, 5 (10), 8-tetraene (VIIIa) in 80-90% yields, which also immediately shows maximum absorption at 372 nm in conc. H2SO4 (Chart 2). Formation of the stable carbocation III seemed to be slow in the case of estradiol-3-methyl ether (II). No χ-372 but χ-465 was formed in conc. H2SO4 with estrone methyl ether (I) which is in higher oxidation state than those of II, IV, V, VI, and VII (Fig. 1).
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  • HIROKO KAWAMURA
    1976 Volume 24 Issue 2 Pages 186-192
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    The metabolites of 7-methylbenzo [α] anthracene (MBA) by NADPH requiring microsomal system from livers of phenobarbital-treated hamsters were analyzed by using 3H-MBA. Then, these systems were applied to the reactions of MBA with the calf thymus DNA. The binding ratio of 3H-MBA to DNA was estimated at 8 mμg of MBA/mg DNA, that is, 1 mole of MBA/100000 nucleotides. The fluorescence spectra indicate an analogy of delocalized electronic system to the parent hydrocarbon, but an evident difference from the DNA-MBA epoxide in the K-region. The formation, observed on the spectra, of MBA-DNA complex by microsomal system was similar to that of MBA-DNA complex by cell cultures.
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  • TAKAHIRO FUTAMI, YOSHIO AIZAWA
    1976 Volume 24 Issue 2 Pages 193-199
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    The effect of surface-active agent on the active transport of sodium in the frog skin was studied. It was assumed that alkyldimethylbenzylammonium chloride (alkyl-DBAC) in 10-3M concentration inhibited the active transport of sodium accompanied with Na+-K+ adenosine triphosphatase (ATP ase), whereas it increased the influx and outflux of 34Na through the frog skin probably due to the structural damage on the frog skin. This effect was observed above the critical micellar concentration of this surfactant. The increased influx of 24Na was decreased by the addition of 1 μg Pi/ml of phospholipid to 10-3M alkyl-DBAC, but it still remained at a higher level. The effect of phospholipase C on the active transport of sodium in the frog skin was different from that of alkyl-DBAC, and 0.5 mg/ml of phospholipase C also increased the influx of 24Na, whereas the increased influx of 24Na was depressed by 10-5M ouabain.
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  • MASATOSHI YAMATO, KUNIKO HASHIGAKI
    1976 Volume 24 Issue 2 Pages 200-203
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    The structure of agrimonolide, isolated as a constituent of Agrimonia pilosa LEDEB. in 1958, was confirmed by the synthesis to be 6, 8-dihydroxy-3-(p-methoxyphenylethyl-3, 4-dihydroisocoumarin.)
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  • HISASHI ICHIBAGASE, YORISHIGE IMAMURA, HIROAKI NAKAGAMI
    1976 Volume 24 Issue 2 Pages 204-210
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    Effect of protein binding on permeation of sulfonamides through a cellophane membrane was investigated by use of a dynamic dialysis technique. The membrane permeation of sulfadimethoxine and sulfamethoxypyridazine that showed high binding to bovine serum albumin (BSA) was significantly increased by the presence of BSA in the receptor compartment, while the membrane permeation of sulfanilamide that showed little binding to BSA was not changed at all by the presence of BSA. Further the increase in the membrane permeation of sulfadimethoxine and sulfamethoxypyridazine in the presence of BSA was significantly depressed by the addition of salicylic acid. Also, salicylic acid strongly displaced sulfadimethoxine or sulfamethoxypyridazine from its protein binding sites. These results suggest that the depressive effect of salicylic acid on the membrane permeation of sulfadimethoxine and sulfamethoxypyridazine in the presence of BSA is due to its displacing activity.
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  • MASATOSHI HARADA, YUKIHIRO OZAKI
    1976 Volume 24 Issue 2 Pages 211-214
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    Effect of six indole alkaloids and one synthetic compound on neuromuscular transmission was examined in the rat limb preparation in situ. Gardneramine inhibited the gastrocnemius contractions elicited by electrical stimulation of the sciatic nerve, but exerted little or no inhibition on the contractions elicited by direct stimulation of the muscle. The inhibitory effect of gardneramine was a little stronger than that of hexamethonium and was very weak when compared with that of d-tubocurarine. Gardnerine augmented both contractions elicited by nerve and muscle stimulation. Gardnutine, hydroxygardnutine, hirsutine, and one synthetic compound showed a long-lasting depressive effect on both contractions, while isorhynchophylline was little effective. These results indicate that only gardneramine affects neuromuscular transmission chiefly.
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  • KATSUHIRO OTSUKA, YO MORI
    1976 Volume 24 Issue 2 Pages 215-219
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    The effect of calcium chelate ethylenediaminetetraacetate (Ca-EDTA) and D-penicillamine on the content of hexosamine-containing substances in the carrageenin granuloma in rats was tested by means of their daily local injection into pre-formed granuloma pouch during 3 or 4 days. The administration of Ca-EDTA revealed involution of pre-formed granuloma and significantly decreased the content of glycosaminoglycans (especially, hyaluronic acid and chondroitin sulphate A) and glycoproteins. However, when Ca-EDTA and D-penicillamine were simultaneously administered or D-penicillamine was given 8 hr after the injection of Ca-EDTA, involution of granulomatous tissue and degradation of both hexosamine-containing substances were completely inhibited. Free N-acetyl-β-glucosaminidase activity in granuloma also increased by treatment with Ca-EDTA, while free enzyme activity recovered to the control level by simultaneous treatment with Ca-EDTA and D-penicillamine. These results obtained here were discussed in relation to the mode of action of D-penicillamine as an antirheumatic drug.
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  • MITSUGI KOZAWA, KIMIYE BABA, TOMOKO ARIMA, KIYOSHI HATA
    1976 Volume 24 Issue 2 Pages 220-223
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    A xanthone glucoside, dillanoside, was isolated from the ethyl acetate extract of a crude drug, dill (Zira), the fruits of Anethum graveolens L. (Umbelliferae), and it was elucidated as 9, 11-dihydroxy-2-methoxybenzo [a] xanthone 9-O-β-D-glucoside (I).
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  • KENJI WATANABE, SHIGESHI TAKESUE
    1976 Volume 24 Issue 2 Pages 224-229
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    The germination of Bacillus megaterium spores both in nutrient broth and in a germinant (L-alanine plus inosine in phosphate buffer) was inhibited by alkyl p-hydroxybenzoates at lower concentrations than those required for inhibiting the outgrowth of germinated spores. The inhibition occurred even when the drugs were added to the spore suspensions where germination had already begun. The degree of inhibition was proportional to the logarithm of alkyl p-hydroxybenzoate concentration present in the germination medium. The concentrations required to completely inhibit germination were 4.5 mM for methyl, 1.6 mM for ethyl, 0.52 mM for propyl, 0.80 mM for isopropyl, 0.22 mM for butyl and 0.22 mM for isobutyl p-hydroxybenzoate. respectively. Free p-hydroxybenzoic acid had no inhibitory activity. There was a linear relationship between the logarithm of germination inhibiting concentration and the number of carbon atoms in the alkyl chain. The inhibition of spore germination by alkyl p-hydroxybenzoates was reversible, since removal of the drugs from spore environment allowed germination to proceed. The possible mechanism of the inhibitory effect of alkyl p-hydroxybenzoates on spore germination is discussed.
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  • MASASHI TOMODA, NORIKO SATOH
    1976 Volume 24 Issue 2 Pages 230-234
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    A mucous polysaccharide, named paniculatan, has been isolated from the inner barks of Hydrangea paniculata SIEB. It was homogeneous by ultracentrifugal analysis and on glass-fiber paper electrophoresis. It was composed of L-rhamnose : D-galactose : 4-O-methyl-D-glucuronic acid : D-galacturonic acid in the molar ratio of 8 : 16 : 10 : 23. The O-acetyl groups in it were identified and the content was 2.0%. Molecular weight of its ammonium salt was estimated at 109000. Periodate oxidation study suggested that the polysaccharide has the high branching structure, whose terminals are occupied by all of 4-O-methyl-D-glucuronic acid units and by about three fourth of D-galacturonic acid units.
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  • YOSHIFUMI MAKI
    1976 Volume 24 Issue 2 Pages 235-237
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    Reduction of 5-phenyl-7-substituted aminofurazano (3, 4-d) pyrimidines with sodium borohydride was undertaken. In a sharp contrast with the cases of amino, alkylamino and tosylamino derivatives, the presence of acetyl group on the C7-amino function results in the smooth reduction of the amidine C=N bond to give 7-acetamido-6, 7-dihydro derivative. The presence of benzoyl group led to the formation of 6, 7-dihydro derivative accompanied with loss of benzamide. Analogously, reduction of 5-phenyl-7-ethylthiofurazano (3, 4-d) pyrimidine gave the 6, 7-dihydro derivative.
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  • TAKEO HIGASHINO, MASAMI GOI, EISAKU HAYASHI
    1976 Volume 24 Issue 2 Pages 238-252
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    Dimerization of π-deficient heterocyles by the catalytic action of cyanide ion in DMSO was carried out. Thus, reaction of quinoxaline (V), 1-phenyl-1H-pyrazolo [3, 4-d] pyrimidine (VI), 1-methyl-1H-pyrazolo [3, 4-d] pyrimidine (VII), and pyrido [2, 3-b] pyrazine (VIII) with cyanide ion gave 2, 2'-biquinoxaline (IX), 4.4'-bis [1-phenyl-1H-pyrazolo [3, 4-d] pyrimidine] (X), 4, 4'-bis [1-methyl-1H-pyrazolo [3, 4-d] pyrimidine] (XI), and 2, 2'-bipyrido [2, 3-b] pyrazine (XII), respectively, although the yields of these dimers were very poor. The formation of dimer is assumed to be oxidation following a benzoin condensation-like reaction by the catalysis of cyanide ion. Also we carried out the reaction of π-deficient heterocycles with aromatic aldehyde (XVI) in the presence of cyanide ion in DMSO, and found that the expected cross benzoin condensation-like reaction has developed. Thus, 4-isoquinolinecarbonitrile (II) reacted with XVI to give α-aryl-4-cyano-1-isoquinolinemethanol (XIX) and aryl 4-cyano-1-isoquinolyl ketone (XX) together with 1, 1'-biisoquinoline-4, 4'-dicarbonitrile (IV). Similarly, V and XVI gave α-aryl-2-quinoxalinemethanol (XXI) and aryl 2-quinoxalinyl ketone (XXII), VI and XVI afforded α-aryl-1-phenyl-1H-pyrazolo [3, 4-d] pyrimidine-4-methanol (XXX) and aryl 1-phenyl-1H-pyrazolo [3, 4-d] pyrimidin-4-yl ketone (XXXI), VII and XVI produced α-aryl-1-methyl-1H-pyrazolo [3, 4-d] pyrimidine-4-methanol (XXXIV) and aryl 1-methyl-1H-pyrazolo [3, 4-d] pyrimidin-4-yl ketone (XXXV), and VIII and XVI formed aryl 2-pyrido [2, 3-b] pyrazinyl ketone (XXXIV). It seems that XIX, XXI, XXX, and XXXIV are a formal product of a cross benzoin condensation-like reaction, and XX, XXII, XXXI, XXXV, and XXXVI are oxidation product of a formal product of the reaction. And limitation of this reaction was also discussed.
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  • TZONGDANN LIN, NORIKO KONDO, JUNZO SHOJI
    1976 Volume 24 Issue 2 Pages 253-261
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    Chikusetsusaponin I, Ia, Ib, IVa, and glycoside P1, the minor saponins and fattyacylglycoside of Panacis japonici rhizoma (rhizome of Panax japonicum C. A. MEYER) have been isolated. The structure of these saponins have been established as 1, 2, 3, 4, and 5, respectively. Chikusetsusaponin I is identical with ginsenoside-Rg2, isolated from P. ginseng C. A. MEYER, while chikusetsusaponin IVa is identical with saponin C, isolated from P. pseudoginseng subsp. himalaicus var. angustifolius.
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  • HIROSHI HARA, OSAMU HOSHINO, BUNSUKE UMEZAWA
    1976 Volume 24 Issue 2 Pages 262-265
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    By the treatment of the p-quinol acetate (IIa-c) with trifluoroacetic acid, (±)-domesticine (VIa), (±)-thaliporphine (VIb), and (±)-1-hydroxy-2, 9, 10, 11-tetramethoxyaporphine (VIc) were given in good yields, respectively.
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  • ISAO KITAGAWA, TAMIO SUGAWARA, ITIRO YOSIOKA, KAORU KURIYAMA
    1976 Volume 24 Issue 2 Pages 266-274
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    Three antifugal glycosides named holotoxin A (major), B, and C have been isolated from the Far Eastern sea cucumber Stichopus japonicus SELENKA. Aqueous acid hydrolysis of holotoxin A furnished genin-1 (a mixture of stichopogenin A2 (3b) and the isomer) and stichopogenin A4 (=genin-2) (3a) in addition to xylose, quinovose, 3-O-methyl-glucose, and glucose, while mild methanolic acid hydrolysis of holotoxin A gave 3a and another new aglycone named 25-O-methyl-stichopogenin A4 (=genin-3) (3c). On the basis of chemical and physicochemical evidence, the structure of stichopogenin A4, the genuine aglycone of holotoxin A, has been elucidated to be expressed as 3a rather than previously proposed 2, and the structure of 25-O-methyl-stichopogenin A4 as 3c.
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  • ISAO KITAGAWA, TAMIO SUGAWARA, ITIRO YOSIOKA
    1976 Volume 24 Issue 2 Pages 275-284
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    The structure of holotoxin A, the major antifungal glycoside isolated from the Far Eastern sea cucumber Stichopus japonicus SELENKA, has been elucidated as 4 on the bases of chemical and physicochemical evidence and enzymatic hydrolysis. Holotoxin B (14), a minor antifungal glycoside of the same origin, has been suggested to be the glucoside of holotoxin A (4) on the similar basis. Holotoxin C, another minor glycoside, has been suggested to be the similar type of glycoside as holotoxin A and B. Holotoxin A and B are distinctive by the possession of two α-linkages of D-xylose and D-quinovose in the oligosaccharide portion. Finally, comparison of the anti-microbial activity of holotoxins with the various kinds of saponins isolated from the plant materials has been presented.
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  • TADAO SATO, TOHRU HINO
    1976 Volume 24 Issue 2 Pages 285-293
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    Heating of dipotassium salt of 3, 6-dicarboxy-1, 4-dimethyl-2, 5-piperazinedione (4) with sulfur monochloride in dioxane gave 1, 4-dimethyl-3, 6-epidithio-2, 5-piperazinedione (11) in 33% yield with simultaneous decarboxylation. When the reaction mixture from 4 and S2Cl2 was reduced with NaBH4 and ethylated with ethyl iodide, cis 3, 6-bis (ethylthio) derivative (17) was obtained in 50% yield besides a trace amount of trans isomer (18) and the monoethylthio derivative (19). Reactions of other metal salts (16a, 16b, and 16c) with S2Cl2 did not improve the yield of 11. On the other hand the reaction of 4 with ethanesulfenyl chloride in dioxane did not yield 17, but gave 18, 19, and hydroxylated compounds (20, 21, and 22) in low yields. Similar results were obtained in the reaction of 4 with benzenesulfenyl chloride. The mechanism of the decarboxylative C-S bond formation was also discussed.
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  • ISAO KITAGAWA, MINORU YOSHIHARA, TADATO TANI, ITIRO YOSIOKA
    1976 Volume 24 Issue 2 Pages 294-302
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    A new diterpene dialdehyde named linaridial was isolated from the ether extractive of fresh subterranean part of Linaria japonica MIq. (Scrophulariaceae), and the structure has been established as 1 on the basis of the physicochemical evidence and the chemical correlation with known 5β-methyl-cis-furano-clerodane (7). Linaridial (1) is the first example of a cis-clerodane-type diterpene isolated from the scrophulariaceous plant. The examination of the MeOH extractive of the same plant has revealed the presence of two linaridial-analogues (LJ-1 (major) and LJ-2 (minor)) along with the small amount of linaridial (1). The structures, 11 and 12, have been assigned to LJ-1 and LJ-2, which seem to be the artefacts formed secondarily from linaridial (1) during the hot MeOH extraction procedure.
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  • TETSUZO KATO, MASAKI NODA
    1976 Volume 24 Issue 2 Pages 303-309
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    Reactions of acetoacetamide (I) and β-aminocrotonamide (II) with 1, 3-dioxo and related compounds were investigated. Namely, the reaction of I with 2, 4-pentanedione (III), 4-methoxy-3-pentene-2-one (VIII), 2-formylcyclohexanone (IV), 4-hydroxy-3-butene-2-one (Va), ethyl 2-ethoxymethyleneacetoacetate (Vb), and 3-ethoxymethylene-2, 4-pentanedione (Vc) afforded 3-acetyl-4, 6-dimethyl-2 (1H)-pyridone (IX), 3-acetyl-5, 6, 7, 8-tetrahydro-2-quinolone (X), 3-acetyl-6-methyl-2 (1H)-pyridone (XIa), ethyl 5-acetyl-6-methyl-2 (1H)-pyridone-3-carboxylate (XIb), and 3, 5-diacetyl-6-methyl-2 (1H)-pyridone (XIc), respectively. On the other hand, the reaction of II with III, 4-amino-3-penten-2-one (VI), 4, 4-dimethoxy-2-butanone (VII), and IV resulted in the formation of 2, 4, 6-trimethyl-3-pyridinecarboxamide (XII), 2, 6-dimethyl-3-pyridinecarboxamide (XV), and 2-methyl-5, 6, 7, 8-tetrahydro-3-quinolinecarboxamide (XIV), respectively. In the case of the reaction of II with Vb, ethyl 5-carbamoyl-2, 6-dimethyl-3-pyridinecarboxylate (XVIIa), ethyl 2-[(2-carbamoyl-1-methylvinylamino) methylene] acetoacetate (XVIIIa) were obtained. Similarly, II reacted with Vc to give 5-acetyl-2, 6-dimethyl-3-pyridinecarboxamide (XVIIb) and 3-[(2-carbamoyl-1-methylvinylamino) methylene]-2, 4-pentanedione (XVIIIb).
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  • SHINZO KANO, EIJI KOMIYAMA, KOUJI NAWA, SHIROSHI SHIBUYA
    1976 Volume 24 Issue 2 Pages 310-314
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    Reactions of dibenzo [b, g] indolizinium iodide (5), (13), (19) with sodium methylsulfinylmethanide were examined and the substantial differences were observed between the phenolic dibenzo [b, g] indolizinium iodide (5), (13) and non-phenolic one (19). Dibenzo [b, f] azonines (7) and (15), formed through the fission of the C12a-N bond, were obtained from 5 and 13, respectively, as main products. The 2-phenylindoline (21) was yielded from 19 by the fission of the C6-N bond.
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  • MASAKATSU SHIBASAKI, SHIRO TERASHIMA, SHUNICHI YAMADA
    1976 Volume 24 Issue 2 Pages 315-322
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    It was found that direct hydrolysis of the crude oxazolidine derivatives (3a, b), prepared with dl-α-cyclocitral (dl-1a), or its 6-benzoxy derivative (dl-1b) and (S) (+)-prolinol ((S) (+)-4), with aqueous acetic acid, afforded (R) (+)-1a, 19% optically pure, and (S) (+)-6-hydroxy-α-cyclocitral ((S) (+)-2b), 63% optically pure, respectively. A merit of the resolution method is that optically active (R) (+)-1a or (S) (+)-2b can be obtained without any recrystallizations. Some mechanistic studies and discussions on the hydrolysis were also examined. Optically active (S) (+)-2b, thus obtained, was successfully converted into (S) (+)-dehydrovomifoliol ((S) (+)-5) via (S) (+)-6-hydroxy-α-ionone ((S) (+)-9). By this chemical conversion, (S) (+)-abscisic acid could be formally synthesized from dl-1b.
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  • KAZUO IMAEDA, TAKEO KURIKI, KEIKO OHSAWA
    1976 Volume 24 Issue 2 Pages 323-325
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    Oxygen determination in thallium and thallium compounds was investigated by a modification of the Schutze-Unterzaucher method. When oxygen in thallium compounds was determined by the conventional method for organic compounds, the oxygen content in almost all samples was 1-5% less than the calculated value. A silica tube that was used for heat decomposition was subjected to erosion by thallium (I) oxide produced by the pyrolysis of thallium compounds and cracks were caused. In order to prevent this, the inside wall of the silica tube was coated with carbon which had been produced by the pyrolysis of naphthalene. Carbon powder was also added into the sample boat to reduce thallium oxides formed by the decomposition of thallium compounds. All of the oxygen in thallium and thallium compounds was determined according to the proposed method, and quite favorable results could be obtained. About 40 min was required for one determination.
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  • TADAHIRO SAWAYAMA, HIROAKI KINUGASA, HARUKI NISHIMURA
    1976 Volume 24 Issue 2 Pages 326-329
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    The absolute configuration of optically active α-hydrazinoornithine which was prepared by the reaction of hydrazine with the α-bromo acid derived from L-ornithine was proved to be the D-configuration. In addition, racemic α-hydrazinoornithine was first prepared by two different methods.
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  • KEIKO MIYASAKA, TADASHI MANABE, MASUMI KOISHI
    1976 Volume 24 Issue 2 Pages 330-336
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    A modified penetration rate method was used successfully to evaluate the wetting properties of magnesium oxide powders. The Washburn equation was employed for analysing experimental data on the assumption that penetrating liquids rise in large number of capillaries formed by particles in the powder bed. The particle size dependency of penetration rate and γ·cos θ was discussed based on the results obtained.
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  • EIICH FURUSAWA, SHINOBU FURUSAWA, SHOHEI TANI, HIROSHI IRIE, KEISUKE K ...
    1976 Volume 24 Issue 2 Pages 336-338
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    Reinvestigation of the alkaloidal constituents of Narcissus tazetta L. revealed that the main alkaloid was pretazettine, although the main alkaloid of this plant had been reported to be tazettine and also provided a convenient and efficient scheme for isolation of pretazettine.
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  • YOSHIHARU SAKUMA, SHIGERU MATSUMOTO, TOMOHISA NAGAMATSU, FUMIO YONEDA
    1976 Volume 24 Issue 2 Pages 338-341
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    The treatment of 6-anilinouracils with potassium nitrate in acetic acid in the presence of sulfuric acid led to the exclusive formation of the corresponding alloxazine 5-oxides. Similarly, the treatment of 6-benzylidenehydrazino-1, 3-dimethyluracils with the same reagents gave the corresponding fervenulin 4-oxides.
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  • TADASHI KOMETANI, SHUNSAKU SHIOTANI, KEMMOTSU MITSUHASHI
    1976 Volume 24 Issue 2 Pages 342-349
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    Forty-seven tert. amines were examined in order to observe the relative lability of the various N-substituents in respect to cleavage by ClCO2Et in refluxing benzene. The aromatic amines did not react with ClCO2Et, while aliphatic and alicyclic amines were cleaved to give carbamate (s) ; the tendency to cause R-N cleavage was : benzyl>allyl>methyl>ethyl>other alkyl groups. It was found that the reaction of a tert. amine with ClCO2Et is greatly influenced by the polarity of the solvent, reaction temperature and N-substituents.
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  • YUKIHISA KURONO, KEN IKEDA, FUMIKO YAMAMURA, TOSHIHISA YOTSUYANAGI
    1976 Volume 24 Issue 2 Pages 349-352
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    Effect of N-alkyl substituents on the formation and hydrolysis rates of N-substituted aniline methanesulfonic acid derivatives were investigated in connection with substituted aniline derivatives. Their rates were satisfactorily correlated to the basicity of aniline derivatives which was corrected by hydration effect, that is Folkers, et al.'s H value.
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  • HIROSHI HOJO, YASUO SUZUKI, MITSURU UCHIYAMA
    1976 Volume 24 Issue 2 Pages 352-355
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
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    Three glucan and a mannan preparations from baker's yeast (Saccharomyces cerevisiae) were examined for their effects on aminopyrine N-demethylase activity and cytochrome P-450 content of liver, and phagocytic activity in mice. Dextran and pustulan were also examined. Among the polysaccharides tested, insoluble glucan mostly decreased cytochrome P-450 content and aminopyrine N-demethylase activity, and stimulated phagocytic activity. Alkaline soluble glucan, mannan, and pustulan decreased a little of cytochrome P-450 at high dose, whereas water-soluble glucan residue produced by acetolysis affected neither cytochrome P-450 content nor phagocytosis.
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  • TETSUZO KATO, MASATSUGU KONDO
    1976 Volume 24 Issue 2 Pages 356-359
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
    JOURNAL FREE ACCESS
    Reaction of diketene with ethyl pyridineformimidates (Ia-e) resulted in the formation of 6-methyl-2-pyridyl-4H-1, 3-oxazin-4-one (IVa-c) and 2-ethoxy-6-methyl-2-pyridyl-2H-1, 3-oxazin-4 (3H)-one (IIIb, c). Similar reaction with ethyl 2-quinolineformimidate (Id) and methyl 2-pyridineacetimidate (Ie) gave 6-methyl-2-(2-quinolyl)-4H-1, 3-oxazine-4-one (IVd) and 2-methoxy-6-methyl-2-(2-pyridylmethyl)-2H-1, 3-oxazin-4 (3H)-one (IIIe), respectively. The products obtained were treated with ammonia to give 6-methyl-2-substituted-4 (3H)-pyrimidone (Va-e). Hydrolysis of IIIe gave 6-hydroxy-4-methyl-3 (or 5)-(2-pyridyl)-2 (1H)-pyridone (VIII).
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  • YOSHIHIKO MORIYAMA, TAKEYOSHI TAKAHASHI
    1976 Volume 24 Issue 2 Pages 360-362
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
    JOURNAL FREE ACCESS
    The structures of three new sesquiterpenes isolated from Ligularia Fauriei (FR.) KOIDZ. were shown to be 1, 2, and 3, respectively.
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  • AKIRA YOSHIDA, SADAO OIDA, EIJI OHKI
    1976 Volume 24 Issue 2 Pages 362-365
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
    JOURNAL FREE ACCESS
    2-Ethoxy-3-cephem-1β-oxide (3) was found to be thermally unstable and easily converted into isothiazolones (4, 5, 6, 9, 10), and the β-lactam derivative (8) under varying reaction conditions. Furthermore, 2-ethoxy-3-cephem (2) was treated with tert-butyl hypochlorite, giving the azetidinone-oxazoline acetate (14).
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  • YASUO FUJIMOTO, TAKESHI SHIMIZU, TAKASHI TATSUNO
    1976 Volume 24 Issue 2 Pages 365-367
    Published: February 25, 1976
    Released on J-STAGE: March 31, 2008
    JOURNAL FREE ACCESS
    An abnormal, stereospecific chlorination of 3-hydroxy-4, 5-epoxy-6, 11βH-eudesm-1-en-6, 12-olide (5, 6, 7 and 8) with methanesulfonyl chloride (or p-toluenesulfonyl chloride)-pyridine is described. The stereochemistry of the chlorides (9, 10, 11 and 12) were confirmed by their nuclear magnetic resonance spectra and chemical reactions.
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