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YOSHIHISA OKAMOTO, TAKEO UEDA
1975 Volume 23 Issue 7 Pages
1391-1395
Published: July 25, 1975
Released on J-STAGE: March 31, 2008
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In the presence of hydrochloric acid, o-(2, 2-dicyanovinyl) aminoaniline is easily converted into 4-amino-1H-1, 5-benzodiazepine-3-carbonitrile, which can be hydrolyzed with various bases to other diazepine, triazepine or benzimidazole derivatives. Ethyl 4-amino-1H-1, 5-benzodiazepine-3-carboxlate and other 1, 5-benzodiazepine derivatives were also obtained from similar reactions. A remarkable tautomeric nature of compound (IX) is also reported.
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YASUHIRO FUJIWARA, SHOSHICHIRO KIMOTO, MASAO OKAMOTO
1975 Volume 23 Issue 7 Pages
1396-1403
Published: July 25, 1975
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Four stereoisomers of 3-methylhexahydrophthalide (IVa, IVb, IVc, and IVd) were synthesized. The stereochemical correlations including the ring juncture and the configurations of methyl groups of these compounds and also the conformations of the methyl groups were investigated by chemical means and by proton magnetic resonance and mass spectrometry.
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NAOKI NAMBU, SHOTARO SAKURAI, TSUNEJI NAGAI
1975 Volume 23 Issue 7 Pages
1404-1410
Published: July 25, 1975
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The physico-chemical properties of several antidepressants were studied in comparison with those of tranquilizing phenothiazines, intending to obtain some information useful to understanding of biopharmaceutical and pharmacological mechanisms of antidepressants. The adsorption isotherms of drug by carbon black (CB) were all observed in Langmuir type. The results suggested that the aromatic rings of drug molecules participate in the adsorption and that there is no special difference in behavior at the surface of CB between antidepressants and phenothiazines. Radii of drug molecule were evaluated by various methods, i. e., r
1 from the molecular volume, r
2 from the assembled Stuart type molecular model, r
3 from the area occupied by one molecule at the surface of CB in the adsorption, and r
4 from the apparent diffusion constant in the cellulose membrane permeation, giving a good correlation between r
1 and r
4. Then the permeation through cellulose membrane was considered to belong to the simple diffusion through small pores. Contrary to such a previous investigation as in the case of barbiturates, there was no clear relationship among the parameters to indicate the hydrophobicity, i.e., the adsorbability onto hydrophobic adsorbent CB, partition coefficient between n-octanol or chloroform and buffer solution, and the surface tension. It was found that both lytic effect of histamine-contraction and inhibitory effect of adrenaline-contraction have relation to the adsorbability onto CB from aqueous solution.
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YOSHIHISA MIZUNO, YOSHIBUMI WATANABE, KAZUYOSHI IKEDA, JAMESA. MCCLOSK ...
1975 Volume 23 Issue 7 Pages
1411-1416
Published: July 25, 1975
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A new type of ketosugar-nucleoside, 7-(5-O-trityl-2, 3-dideoxy-2-oxo-α-D-pento-furanosyl) hypoxanthine (VIII) and a new type of purinecyclonucleoside, 5'-O-trityl-3', 6-anhydro-7-α-D-arabinofuranosylhypoxanthine (VI) were synthesized from 5'-O-trityl-2', 3'-di-O-mesyl-α-D-arabinofuranosylhypoxanthine (IV).
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MAMORU SUGIURA, MASAKAZU ISOBE, FUMIO HIRATA, TOSHIWO INAGAWA
1975 Volume 23 Issue 7 Pages
1417-1420
Published: July 25, 1975
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A method for the assay of triglyceride in human serum was attempted by hydrolysis of triglyceride with lipoprotein lipase and measurement of released free fatty acid by titrimetry according to the method of Dole. Triglyceride in serum was completely hydrolyzed to glycerol and free fatty acid with the lipoprotein lipase produced from Pseudomonas sp. in a short time. It was found that the lipoprotein lipase was useful as a reagent for clinical examination. Data from the Dole method with lipoprotein lipase were parallel to those from the Van Handel and Zilversmit method, which has frequently been employed.
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KANETO UEKAMA, MASAKI OTAGIRI, YOUKO KANIE, SHIGEO TANAKA, KEN IKEDA
1975 Volume 23 Issue 7 Pages
1421-1430
Published: July 25, 1975
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Inclusion complexation of various trans- and cis-cinnamic acid derivatives with α-and β-cyclodextrins in aqueous solution was studied by circular dichroism (CD), ultraviolet (UV), and nuclear magnetic resonance (NMR) spectroscopies. By the analyses of the induced CD and UV spectral changes, the spatial relationships between guest and host molecules was investigated. To elucidate the inclusion mechanism, stoichiometric ratio, which was found 1 : 1, formation constant, and thermodynamic parameters for trans-cinnamic acid-cyclodextrin systems were determined. Various factors in guest molecule such as ionization, hydrophobic nature, and substituent effect were reflected in inclusion formation. From the evidences of sign of the induced CD and NMR chemical shift, it was proposed that phenyl moiety of cinnamic acid was fixed into (R)-configuration within the cavity of cyclodextrin.
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HIROTAKA OTOMASU, KYUJI NATORI, HIROSHI TAKAHASHI
1975 Volume 23 Issue 7 Pages
1431-1435
Published: July 25, 1975
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1'-Substituted spiro [imidazolidine-4, 3'-indoline]-2, 2', 5-triones (5-8) were prepared by the reaction of 1-substituted indoline-2, 3-diones with KCN and (NH
4)
2 CO
3. The reaction of indoline-2, 3-diones with KCN and amines afforded 3-amino-3-cyanoindolin-2-ones (9-11), which on reacting with KOCN, only 9 gave 3-methyl derivative of the spiro compound (16). By the methylation of 6 with (CH
3)
2SO
4, 1', 3-dimethyl-(17) and 1, 1', 3-trimethyl-spiro [imidazolidine-4, 3'-indoline] compound (18) were obtained.
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HIROTAKA OTOMASU, KEI YOSHIDA, KYUJI NATORI
1975 Volume 23 Issue 7 Pages
1436-1439
Published: July 25, 1975
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The reaction of 3-chloro-3-nitromethylindolin-2-one (2a) with aniline resulted the formation of 3-anilinomethylene-(4a) and 3-(p-phenylazo) anilinomethyleneindolin-2-one (5). Chromatographying of 2a, b using Al
2O
2 in chloroform solution gave 3-nitro-methyleneindolin-2-ones (7a, b), which were also reacted with amines to give 3-amino-methyleneindolin-2-ones (4a, b and 8a, b).
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YASUHIRO YAMANE, KAZUO SAKAI
1975 Volume 23 Issue 7 Pages
1440-1445
Published: July 25, 1975
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The mode of elevating action of 4-dimethylaminoazobenzene (DAB) metabolizing enzyme activity in the liver of rats fed copper was studied. The increases of the enzyme activity and flavin content were found with that of copper content in the liver homo-genates and microsomes of rats fed copper. But addition in vitro of cupric ion and/or fravin adenine dinucleotide (FAD) in the reaction mixture involving microsomal prepara-tions did not cause a marked enhancement of the enzyme activity. This fact is thought to indicate the both increases of flavin and apoenzyme. The concurrent administration of copper and 3'-methyl-4-dimethylaminoazobenzene (3'-Me-DAB) showed additive effect in reduced nicotinamide adenine dinucleotide phosphate (NADPH) cytochrome c reductase activity and competitive effect in DAB azo reductase activity.
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HIDEO NAKAMURA, MASANAO SHIMIZU
1975 Volume 23 Issue 7 Pages
1446-1451
Published: July 25, 1975
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Effects of steroidal and non-steroidal anti-inflammatory agents on the accelerated granuloma formation in rats, which was induced by the dual implantation of felt-pellets, were compared with effects on the usual granuloma formation (one time implantation of felt-pellet). The ID
30 % value of anti-granuloma activity of each agent in the usual method was as follows : dexamethasone 0.03mg/kg/day, indomethacin 1.4 mg/kg/day, prednisolone 2.5mg/kg/day, flufenamic acid 18.5 mg/kg/day, phenylbutazone 20.0 mg/kg/day and Aspirin 700 mg/kg/day, p. o. However, indomethacin (2 and 3 mg/kg/day), phenylbutazone (30 and 100 mg/kg/day) and Aspirin (600 mg/kg/day) did not show any signific anti-granuloma activity on the accelerated granuloma formation, and these inhibitory activities were less than 20%. Flufenamic acid showed the activity at 60 mg/kg/day, but did not at 30 mg/kg/day. On the other hand, prednisolone inhibited by the same degree both usual and accelerated granuloma formations at 3 and 10 mg/kg/day, and dexamethasone showed more potent inhibitory activity on the accelerated granuloma formation than that on the usual granuloma formation. These results suggest that the mode of anti-granuloma action of steroidal anti-inflammatory agents may be different from those of non-steroidal anti-inflammatory agents.
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HIROYUKI OKAMOTO, KOUICHI YAMANOUCHI, KAZUMASA YOKOYAMA
1975 Volume 23 Issue 7 Pages
1452-1457
Published: July 25, 1975
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To choose a perfluorochemical as a candidate for the artificial erythrocyte or organ perfusate, screening of perfluorochemicals was performed from the standpoints of persistence of them in the circulation and deposition in the body tissues of rabbits, mice and rats. In view of elimination from the body, perfluorodecalin was found to be the most suitable compound among five different perfluorochemicals examined. As for emulsifiers, egg yolk phospholipid was found to be the first choice on account of its ability to sustain perfluorochemicals for an adequate period in the circulation as well as the feasibility for preparing emulsion among the three emulsifiers examined. It was found also that the smaller the particle size of emulsion, the better suited for an artificial erythrocyte of perfusate.
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HIROSHI HIKINO, TORU OKUYAMA, SHIGENOBU ARIHARA, YASUKO HIKINO, TSUNEM ...
1975 Volume 23 Issue 7 Pages
1458-1479
Published: July 25, 1975
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The structure of shidasterone, the phytoecdysone isolated from Blechnum niponicum (Blechnaceae) has been studied. In connection with this, stereoisomers of the cholestane-20, 22-diol derivatives in regard to C-20 and C-22 have been synthesized and their chemical and spectral properties have been examined. Chemical and physico-chemical data and, in particular, the
13C NMR spectrum of shidasterone have revealed that shidasterone is identified as 22, 25-oxido-5β-cholest-7-en-6-one-2β, 3β, 14α, 20-tetraol (1).
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MASAMI MORI, MASANOBU HAGA, SETSUZO TEJIMA
1975 Volume 23 Issue 7 Pages
1480-1487
Published: July 25, 1975
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The title compounds were synthesized starting from 1, 6-anhydro-β-maltose, via 1, 6-anhydro-4', 6'-O-benzylidene-β-maltose with several steps. Heating of 2, 2', 3, 3'-tetra-O-acetyl-1, 6-anhydro-4', 6'-di-O-mesyl-β-maltose (9) with sodium benzoate in hexamethylphosphosphoric triamide afforded 2, 3-di-O-acetyl-1, 6-anhydro-4-O-(2, 3-di-O-acetyl-4, 6-di-O-benzoyl-α-D-galactopyranosyl)-β-D-glucopyranose (15) as an amorphous powder. Deacylation of 15 and sequential reacetylation gave crystalline hexaacetate (16). The former of the title compound (19), mp 227-229, [α]
26D+159.6°, was obtained after acetolysis of 16 followed by deacetylation. Treatment of 9 with NaI in acetonitrile effected substitution of the mesyloxy at C
6' to give the corresponding 6'-deoxy-6'-iodo-4'-O-mesyl derivative (11), from which 6'-deoxy compound (13) was prepared by catalytic hydrogenation. Benzoyloxy substitution with inversion at C
4'-mesyloxy in 13 gave 2, 3-di-O-acetyl-1, 6-anhydro-4-O-(2, 3-di-O-acetyl-4-O-benzoyl-6-deoxy-α-D-galactopyranosyl)-β-D-glucopyranose (20), from which the latter of the title compound (24), hydroscopic, amorphous powder, [α]
27D+128.3°, was obtained via the same pathway as for 19 from 15. Synthesis and characterization of the key intermediate (9) were described in full detail.
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AKIO MIYAKE, KATSUMI ITOH, NORIO TADA, YOSHIKAZU OKA, SHOJIRO YURUGI
1975 Volume 23 Issue 7 Pages
1488-1499
Published: July 25, 1975
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Reaction of 5, 8-dimorpholino-2-phenylpyrimido [4, 5-d] pyridazine (I) with Grignard reagent or organolithium afforded 4-substituted-3, 4-dihydro derivatives (II). The use of an excess of the reagent gave rise to further substitution at 8-position to afford 4, 8-disubstituted-3, 4-dihydro derivatives (III and VII). Similar results were observed in the reaction of Grignard reagents with analogous tetraazanaphthalene derivatives, 5, 8-dimorpholino-2-phenylpyrimido [4, 5-d] pyrimidine (XX) and 5, 8-dimorpholino-2-phenyl-pyrazino [2, 3-d] pyridazine (XXII), to afford 4-substituted-3, 4-dihydro derivatives (XXI) and 3-substituted-3, 4-dihydro derivatives (XXIII), respectively. Among the obtained derivatives, IIa and IIj exhibited significant diuretic activity.
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AKIO MIYAKE, YOSHIKAZU OKA, SHOJIRO YURUGI
1975 Volume 23 Issue 7 Pages
1500-1504
Published: July 25, 1975
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Photochemical reactions of tetraazanaphthalene derivatives, I, II, and III, with alcohols and cyclic ethers in the presence of photosensitizer resulted in selective addition at the 3, 4 C=N bond to give substituted-3, 4-dihydro derivatives. Potential diuretic activity was shown by many of the obtained compounds.
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AKIO MIYAKE, KATSUMI ITOH, NORIO TADA, YOSHIKAZU OKA, SHOJIRO YURUGI
1975 Volume 23 Issue 7 Pages
1505-1510
Published: July 25, 1975
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Oxidation of a variety of substituted dihydrotetraazanaphthalene derivatives (I-IV) with 2, 3-dichloro-5, 6-dicyanoquinone afforded corresponding dehydrogenated aromatic deriva tives (V, VII, IX, and X). However, oxidation with potassium ferricyanide, bromine or nitrobenzene gave rise to oxidative elimination of the substituent in addition to normal dehydrogenation, depending upon the variety of the substituent. The substi-tuents readily removed by this novel C-C bond cleavage were benzyl, allyl, tert-butyl, cyclohexyl and α-hydroxyalkyl groups.
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TAKASHI HARAYAMA, MITSUAKI OHTANI, MASAHARU OKI, YASUO INUBUSHI
1975 Volume 23 Issue 7 Pages
1511-1515
Published: July 25, 1975
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Total synthesis of dl-serratinine (1 : dl-form) has been completed as follows. The Wittig reaction of the aldehyde (6) with diethylcyanomethylphosphonate gave the conju-gated nitrile (7) which was subjected to hydrogenation, followed by NaBH
4-CoCl
2 reduction to provide the primary amine (10). Treatment of (10) with NCS and Cu
2Cl
2 gave the aziridine A (11) and the aziridine B (12). The aziridine A was derived to the aziridinium salt (14) via the primary alcohol (13) and its tosylate, and the reaction of 14 with AcOK afforded the triacetate (15). Hydrolysis of 15, followed by oxidation with Jones'reagent gave the triketone (18). Finally, reduction of 18 with NaBH
4 afforded dl-serrat-inine (1 : dl-form) and dl-8-episerratinine (19 : dl-form).
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HIDEO UTSUMI, YUTAKA KIRINO, TAKAO KWAN
1975 Volume 23 Issue 7 Pages
1516-1519
Published: July 25, 1975
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L-Ascorbic acid and its analogs were found to react with hydrazine and substituted hydrazines in an aerobic, alkaline aqueous solution to give rise to some stable radical inter-mediates. The ESR parameters of the radical species were determined, and a possible radical structure common to all the reactions concerned was presented.
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ISAO KITAGAWA, YASUHIRO IMAKURA, TERUAKI HAYASHI, ITIRO YOSIOKA
1975 Volume 23 Issue 7 Pages
1520-1531
Published: July 25, 1975
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The full detail of the chemical evidence on the structure of jegosapogenin (=21-O-tigloyl-barringtogenol C (Ia)), which was obtained along with barringtogenol C (I) and barringtogenol D (II) by acid hydrolysis of the pericarps saponin (=jegosaponin) of Styrax japonica SIEB. et ZUCC. (Styracaceae), is described. The structure of desacyl-jegosaponin, which is a common desacylated product of the saponin constituents of jegosaponin, and was prepared in a high yield by alkaline treat-ment of jegosaponin, has been established as barringtogenol C (3)-[β-D-glucopyranosyl-(1
glu→2
glr)][α-L-rhamnopyranosyl (1
rham→2
gal)-β-D-galactropyranosyl (1
gal→4
glr)]-β-D-glucuronopyranoside (VIf) on the basis of the chemical and physicochemical evidence.
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MAMORU SUGIURA, AKIRA ITO
1975 Volume 23 Issue 7 Pages
1532-1536
Published: July 25, 1975
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Hydrolysis actions of dextranase (EC 3. 2. 1. 11) from Brevibacterium fuscum var. dex-tranlyticum on dextrans with various molecular weights (5.0×10
3-approx. 1.0×10
7) were investigated comparing with those of Penicillium funiculosum IAM 7013 dextranase. The specific activities were measured as an increase of reducing sugar per min per mg protein at the substrate concentration 1.34%. The activities of B. fuscum dextranase were 110-190 μmoles as glucose for various dextrans. Those of P. funiculosum dextranase were, however, almost constant and approximately 400 μmoles for dextrans examined. The K
m values (%) and V
max values (μmoles/min per mg protein) of B. fuscum dex-tranase decreased with an increase in molecular weight of dextrans. K
m values were 0.041-0.065 and V
max values were 76-128. However, both values of P. funiculosum dextranase were constant, and K
m remained at about 0.2 and V
max was approximately 800. Molecular properties of digestion products by B. fuscum dextranase were investigated. The polymerization degree of the products in the oligosaccharide fraction was constantly 3 in spite of an increase of reducing sugar content in the reaction mixture. Molecular size of the products was also investigated by the gel filtration on Bio Gel P-60. The fractionation patterns were markedly different from those of P. funiculosum dextranase as a typical endo-enzyme. These results indicated that the enzyme acted as an exo-dextranase at early reaction stage, and finally the enzyme might be able to hydrolyze the residual part of the substrate ; i. e. core dextran having branching points.
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MAMORU SUGIURA, MASAKAZU ISOBE, KAZUYUKI HIRANO, SHIRO IINO, HIROSHI S ...
1975 Volume 23 Issue 7 Pages
1537-1541
Published: July 25, 1975
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Alkaline phosphatase (E.C. 3. 1. 3. 1) was extracted from human small intestine by a modified Morton's butanol method and was purified by ammonium sulfate precipitation, and chromatography over diethylaminoethyl (DEAE)-cellulose, carboxymethyl (CM)-collulose, and Sephadex G-200. The homogeneity of the purified enzyme was demon-strated by disc electrophoresis and immunoelectrophoresis. The purified enzyme was activated by MgCl
2, but inhibited by HgCl
2 and CdCl
2. Inactive apoenzyme, prepared by incubation with 2×10
-4M ethylenediaminetetraacetic acid (EDTA) at pH 7.4, is optimally reactivated by Zn
2+. The heat activation for hydrolysis of p-nitrophenyl phosphate was calculated as 9000 cal/mole.
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MAMORU SUGIURA, MASAKAZU ISOBE, KAZUYUKI HIRANO, SHIRO IINO, HIROSHI S ...
1975 Volume 23 Issue 7 Pages
1542-1546
Published: July 25, 1975
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Enzymic properties of purified alkaline phosphatases (ortho-phosphoric monoester phosphohydrolase, E. C. 3. 1. 3. 1) from human small intestinal mucosa and human placenta were compared. Intestinal alkaline phosphatase had similar properties to those of placental alkaline phosphatase with respect to inhibition by L-phenylalanine, isoelectric point, pH stability, optimum pH, and Michaelis constant. However, difference in enzymic properties was found with respect to the molecular weight, heat stability, and the degree of inhibition by phosphate ion.
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SADAO OIDA, HIROMICHI SAEKI, YOSHIHIKO OHASHI, EIJI OHKI
1975 Volume 23 Issue 7 Pages
1547-1551
Published: July 25, 1975
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Following the procedure of Ireland, et al., 3-phosphorodiamidates (1b and 6b) of 1, 2 : 5, 6-di-O-isopropylidene-glucose and -allose were treated with lithium-ethylamine to give a 2, 3-dideoxy compound (3) in good yield, while similar treatment of a glucosaminide 3-phosphorodiamidate (11b) yielded a 3-deoxy derivative (12a). Thus, this method has the advantage of convenience for the preparation of deoxysugars.
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HIDEO SETO, KOJI HAYASHI, HIROSHI MITSUHASHI
1975 Volume 23 Issue 7 Pages
1552-1554
Published: July 25, 1975
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A new polyoxypregnane derivative, tomentosin (12β-O-tigloyl-20-O-acetyl-tomentogenin) was isolated from the stem of Marsdenia tomentosa. Tomentosin is the first example of the diester possessing a tomentogenin skeleton to be isolated from the Asclepiadaceae plant, and it did not undergo any internal acyl migration which occurrs on mild alkaline hydrolysis of C-12β, 20-diester of sarcostin and other polyoxypregnane derivatives.
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KIYOSHI TATSUMI, TOSHIRO YAMAGUCHI, HIDETOSHI YOSHIMURA
1975 Volume 23 Issue 7 Pages
1555-1560
Published: July 25, 1975
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The absorption route of
14C-AF-2 (2-(2-furyl)-3-(5-nitro-2-furyl) acrylamide) and
14C-nitrofurazone (5-nitro-2-furfural semicarbazone) was examined with thoracic duct or portal vein cannulated rats. As a result, it was found that the radioactivity was almost exclusively absorbed via portal system from intestinal tract after administration of the above labeled compounds to rats. In addition, the present study revealed the direct evidences concerning the metabolism of the above nitrofuran derivatives in the intestinal mucosa of rats and the absorption of their metabolites from the intestinal wall. Further-more, it was demonstrated that the absorption rate of radioactivity was lower in 7 weeks old rats than in over 8 weeks old rats after oral administration of
14C-AF-2 and
14C-NF-161 (2-amino-5-[2-(5-nitro-2-furyl)-1-(2-furyl) vinyl]-1, 3, 4-oxadiazole).
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MASAYUKI ONDA, MITSUYO GOTOH, JUNKO OKADA
1975 Volume 23 Issue 7 Pages
1561-1564
Published: July 25, 1975
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The carbinolamine 2 is oxidized with oxygen to give the peroxide 6 whose structure is established on the basis of the spectral properties and the structure of the hexahydro-chelerythrine 7 obtained on the sodium borohydride reduction. Formation pathway of the peroxide 6 is examined. Treatment of the peroxide 6 with 2, 3-dichloro-5, 6-dicyano-benzoquinone (DDQ) affords the keto amide 10, two nitriles 11 and 12, and keto aldehyde 13. Structures for these compounds are mainly proved by the spectral data. Further, it is examined that these compounds are probably formed by oxidation and reduction of the peroxide 6 with DDQ and 2, 3-dichloro-5, 6-dicyanohydroquinone resulted from DDQ during reaction.
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SHUNSUKE NARUTO, HARUKI NISHIMURA, HIDEHIKO KANEKO
1975 Volume 23 Issue 7 Pages
1565-1572
Published: July 25, 1975
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It has been found that the crude acetone adducts of quaternary protoberberinium salts, dehydrocorydalinium chloride (I), 13-methylberberinium chloride (VI) and berberi-nium chloride (VII), were contaminated with about a few per cent of 8, 13a-propanoberbine derivatives, III, X and XI, respectively, as a result of intramolecular Michael condensation of each acetone adduct. The presence of these compounds was deduced from the direct isolation or from the product analysis of the reaction using a crude acetone adduct as a starting material.
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MIYOJI HANAOKA, NOBUO OGAWA, KENJI SHIMIZU, YOSHIO ARATA
1975 Volume 23 Issue 7 Pages
1573-1578
Published: July 25, 1975
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The Mannich reaction of isopelletierine (III) with 3-methoxybenzaldehyde (VI) in aqueous sodium hydroxide afforded the trans- and cis-quinolizidine (VIII and IX) in the 1 : 6 ratio, whereas the reaction with 3-hydroxybenzaldehyde (VII) gave almost exclusively the trans-quinolizidine (X). On the other hand, the reaction with VI in methanol afforded VIII and IX in the 6 : 1 ratio. On the basis of the detailed experiments the Mannich reaction of III with arylaldehyde under an alkaline condition was found to afford at first cis-4-arylquinolizidin-2-one, which then isomerized into the corresponding trans-isomer. And the stereoselectivity of this reaction was found to depend on solvents, solubilities of the starting arylaldehydes and products, and reaction times.
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MINORU SEKIYA, OSAMU MATSUDA, KEIICHI ITO
1975 Volume 23 Issue 7 Pages
1579-1585
Published: July 25, 1975
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The present paper describes a new reaction of N, N'-and N, O-linked methylene compounds with carboxylic acids such as cyanoacetic acid, malonic acid, acetoacetic acid, trichloroacetic acid and phenylpropiolic acid. By the reaction substitution of one of the linking heteroatoms of the substrates by the decarboxylated residues of the carboxylic acids is effected to proceed. The reaction presented here provides an effective means of introducing mono- and/or bis-dialkylaminomethyl grouping into the decarboxylated residue of the carboxylic acids.
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YOSHIHIKO TAGUCHI, YOSHITAKA MUSHIKA
1975 Volume 23 Issue 7 Pages
1586-1588
Published: July 25, 1975
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Reaction of 2-(N, N-dimethylamino)-4-nitrophenyl phosphate (1), a new phosphorylating agent, with the alcohol involving primary and secondary hydroxyl groups led to selective phosphorylation of the primary hydroxyl group. Thus, 1, 2-propanediol and glycerol were phosphorylated to give exclusively the corresponding 1-phosphates. When unprotected nucleosides were treated with this reagent 1, nucleoside 5'-phosphates were obtained in satisfactory yield by simple work up.
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KAZUHIDE KAMIYA, YOSHIKAZU WADA, MASAO NISHIKAWA
1975 Volume 23 Issue 7 Pages
1589-1595
Published: July 25, 1975
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The absolute configuration at C-1 of d-6-chloro-5-cyclohexylindan-1-carboxylic acid (d-TAI-284) has been assigned to the sinister series by X-ray analysis. The conformation of d-TAI-284 was similar to that of indomethacin, which indicates that a hypothetical receptor site contour for indomethacin analogs proposed by Shen is also applicable to d-TAI-284. Importance of conformational structure in determining antiinflammatory activities is suggested.
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NOBUTAKA FUJII, HARUAKI YAJIMA
1975 Volume 23 Issue 7 Pages
1596-1603
Published: July 25, 1975
Released on J-STAGE: March 31, 2008
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Trifluoromethanesulphonic acid was applied to remove the protecting groups, Z and MBzl, from Z-Ala-Gly-Cys (MBzl)-Lys (Z)-Asn-Phe-Phe-Trp-Lys (Z)-Thr-Phe-Thr-Ser-Cys (MBzl)-OH to produce the peptide with somatostatin activity.
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HIROSHI IWASE
1975 Volume 23 Issue 7 Pages
1604-1608
Published: July 25, 1975
Released on J-STAGE: March 31, 2008
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The resolution of racemic amino acids as their l-menthyl ester derivatives was carried out by gas chromatography. Seven stationary phases were studied for the chromatographic separation. The effect of N-perfluoroacyl groups and ester groups on the resolution of racemic amino acids was examined. Relation between separation factor and structure of amino acids has also been discussed.
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HIROSHI IWASE
1975 Volume 23 Issue 7 Pages
1608-1611
Published: July 25, 1975
Released on J-STAGE: March 31, 2008
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The gas chromatographic resolution of racemic amino acids as their N-trifluoroacetyl esters was carried out on an optically active stationary phase. Relation between the sepa-ration factor and structure of racemic amino acids, and relative retention times were studied. It is concluded that the separation factor of racemic amino acids depends on the relative size of the substituent on the asymmetric carbon and the position of amino group.
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KUNIO SUZUKI, TADAKATU SAKAMOTO, MINORU SEKIYA
1975 Volume 23 Issue 7 Pages
1611-1612
Published: July 25, 1975
Released on J-STAGE: March 31, 2008
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There has been found a formic acid reaction of α, N-diphenylnitrone which effects reduction together with introduction of hydroxyl group into a benzene ring, ortho to nitrogen function.
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TOSHIO NAMBARA, YOSHIHIKO KAWARADA
1975 Volume 23 Issue 7 Pages
1613-1616
Published: July 25, 1975
Released on J-STAGE: March 31, 2008
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In order to characterize the biliary metabolites formed from estriol the isomeric monomethyl ethers of 2, 16β-dihydroxy-estrone (IIIa, IIIb) and -estradiol (IVb, IVd) have been synthesized as the reference compounds.
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CHIKARA KANEKO, SACHIKO YAMADA, AKIKO SUGIMOTO, MASAYUKI ISHIKAWA
1975 Volume 23 Issue 7 Pages
1616-1619
Published: July 25, 1975
Released on J-STAGE: March 31, 2008
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As part of a general exploration of the structure/activity relationships of the vitamin D system, the 2β-hydroxylated analogue of cholecalciferol (vitamin D
3) has been prepared from 2β-hydroxy-7-dehydrocholesterol obtained in our previous work as starting material via (i) photochemical conrotatory opening (2 N
f pericyclic reaction) of the B-ring and (ii) thermal 1, 7-antarafacial hydrogen shift (3 N
f pericyclic reaction).
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YOSHIFUMI MAKI, KOJI OZEKI, MIKIO SUZUKI
1975 Volume 23 Issue 7 Pages
1619-1621
Published: July 25, 1975
Released on J-STAGE: March 31, 2008
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Upon treatment with sodium borohydride in pyridine, 1-acetylamino-cis-4-t-butyl-cyclohexane-1-carbonitrile, 2-acetylaminonorbornane-endo-2-carbonitrile and 2-acetyl-aminobornane-endo-2-carbonitrile underwent decyanization to give a mixture of isomeric acetylamino compounds in high yields, respectively. The product distribution can be explained in terms of the preferential attack of a hydride ion on the less-hindered side of the molecules.
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HARUAKI YAJIMA, MASAYUKI KUROBE, IKUKO YO, NOBUTAKA FUJII, YOSHIHIKO B ...
1975 Volume 23 Issue 7 Pages
1622-1624
Published: July 25, 1975
Released on J-STAGE: March 31, 2008
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Solid phase synthesis was applied to prepare a number of LH-FSH-RH analogues. Each constituent amino acid residue of this hypothalamic principle was systematically replaced by Pro. Ten samples thus prepared, after partial purification, were submitted to biological assay. However, none of the inactive peptide, hopefully an inhibitor, was found in these analogues.
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HIROSHI FURUKAWA, ETSUKO SAKAKIBARA, AKIRA KAMEI, KAZUO ITO
1975 Volume 23 Issue 7 Pages
1625-1626
Published: July 25, 1975
Released on J-STAGE: March 31, 2008
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The optical resolution of racemic amino acids by high performance liquid chromato-graphy (MicroPak Si-5, 1.5% iso-PrOH in iso octane) of corresponding diastereomeric N-d-10-camphorsulfonyl p-nitrobenzyl ester can be achieved.
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MORIO FUKUHARA, EIGO TAKABATAKE
1975 Volume 23 Issue 7 Pages
1626-1628
Published: July 25, 1975
Released on J-STAGE: March 31, 2008
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Male rats were fed for 16 days on the diet containing 0.2% of AF2. Hepatic micro-somes were isolated and the activities of mixed function oxidase system were assayed. Cytochrome P-450 was significantly reduced in its content and, on the contrary, cyto-chrome b
5 was much elevated in the AF2-treated animals. AF2 treatment also depressed the activities of aminopyrine N-demethylase and aniline hydroxylase. The changes in the contents of hepatic constituents were also analyzed.
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KEIJI KURATA, MIWAKO MATSUO, HIROYOSHI AWAYA, YOSHINORI TOMINAGA, YOSH ...
1975 Volume 23 Issue 7 Pages
1629-1630
Published: July 25, 1975
Released on J-STAGE: March 31, 2008
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By the reaction of triazacycl [3, 3, 3] azine derivatives (IV) with dimethyl acetylene-dicarboxylate in dimethylformamide or acetonitrile, the two products, namely dimethyl 4-cyano-1, 6-diazacycl [3, 3, 3] azine-2, 3-dicarboxylate (VIa) and tetramethyl 1, 6-diazacycl-[3, 3, 3] azine-2, 3, 4, 5-tetracarboxylate (VIb), were obtained.
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TAKAO MURAKAMI, KIMIKO OWASHI, NOBUTOSHI TANAKA, TOSHIKO SATAKE, CHIUM ...
1975 Volume 23 Issue 7 Pages
1630-1632
Published: July 25, 1975
Released on J-STAGE: March 31, 2008
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Im Zusammenhang mit der chemotaxonomischen Studien der Gattung Pteris und der verwandten Gattungen (Pteridaceae) konnten aus den oberiridischen Teilen von Dennstasdtia scabra (WALL.) MOORE neben dem bereits bekannten Pterosin A zwei Glieder der Pterosin A-Reihe, nahmlich 4-Hydroxy-Pterosin A (II) und Pterosin V (III) isoliert und deren Strukturen aufgeklart werden. Ausserdem konnten Pterosin K (VI) und F (VII) durch eine GC-MS-Analyse identifiziert werden.
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HIDEO UTSUMI, YUTAKA KIRINO, TAKAO KWAN
1975 Volume 23 Issue 7 Pages
1632-1634
Published: July 25, 1975
Released on J-STAGE: March 31, 2008
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L-Ascorbic acid and isoniazid or apresoline were found to produce stable free radical intermediates when coexisted in alkaline aqueous solutions at room temperature. The electron spin resonance parameters and a possible skeletal structure of the radical species were presented.
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TAKAO MURAKAMI, NOBUTOSHI TANAKA, TAKATO TEZUKA, CHIUMING CHEN
1975 Volume 23 Issue 7 Pages
1634-1637
Published: July 25, 1975
Released on J-STAGE: March 31, 2008
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Im Zusammenhang mit der chemotaxonomischen Studien der Gattung Pteris und der verwandten Gattungen (Pteridaceae) wurden aus Pteris inaequalis BAKER var. aequata (MIQ.) TAGAWA Pterosin C, Acetylpterosin C, 5-Hydroxymethyl-2-Furfural, 2-Desoxy-D-Glukose (I), 3, 6-Anhydro-2-desoxy-D-Glukose (II) und 2-Desoxy-D-Glukose-3-Mono-methylather (III) sowie ein Steringlykosid (IV) isoliert und identifiziert. Von ihnen sind II, III, und IV bisher noch nie in der Natur aufgefunden.
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