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Volume 33, Issue 6
Displaying 1-50 of 71 articles from this issue
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MITSUNOBU DOI, NOBUKO YASUDA, TOSHIMASA ISHIDA, MASATOSHI INOUE1985 Volume 33 Issue 6 Pages 2183-2189
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree crystalline forms of bromodiethylacetylurea (named α, β and γ) were characrerized by thermal analyses. The α→β→γ structural conversion was accompanied with endothermic change : the transition temperature and enthalpy change were 70.7-83.0°C, ΔH=0.71 (5) kcal/mol for the α→β transition and 83.0-96.5°C, ΔH=0.65 (4) kcal/mol for the β→γ transition, respectively. The γ-type crystal emerged only between 90 and 110°C. X-Ray analyses were performed for α- and β-type crystals. They have two molecules in the asymmetric unit (molecules A and B for α-type, molecules C and D for β-type). Conformational differences among these molecules were not significant, although the hydrogen bond networks characteristic of the two crystal types may be significant in relation to the bioavailabilities of this drug.View full abstractDownload PDF (579K) -
TETSUO OSA, HIROAKI HINO, SHIGEAKI FUJIEDA1985 Volume 33 Issue 6 Pages 2190-2194
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA kinetic study of Pt-blue complex formation was carried out in a solution containing [Pt (NH3)2 (H2O)2]2+ and uracil under oxygen bubbling, with monitoring by means of an oxygen analyzer and visible spectrometer. The rate of oxygen consumption was first-order with respect to concentration of [Pt (NH3)2 (H2O)2]2+, uracil, or oxygen. A correlation was found between the decrease of oxygen consumption in the solution and the increase of the absorbance at 640 nm, namely formation of the blue complex. The formation mechanism of the blue complex is considered to be 1) first the equilibrium reaction of the coordination of uracil to Pt, 2) next the oxidation of the Pt-uracil complex with oxygen, and 3) finally a follow-up reaction presumably via formation of polynuclear complexes. Eight other blue complexes were formed by the use of N-aromatic base ligands possessing an amide linkage. The oxygen consumption rates of these complexes were found to be large in the case of the ligands which form many structurally isomeric complexes.View full abstractDownload PDF (520K) -
MASAFUMI GOTO, KOUJI MORI, TOMOYA SAKAI1985 Volume 33 Issue 6 Pages 2195-2203
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe factors which govern the induction period in the catalysis of 3-methylindole oxygenation by the title complexes were investigated. Electron spin resonance measurements showed that the superoxo-cobalt complex observed in the induction period disappeared at the start of the steadystate consumption and that the superoxo complex was preferentially converted to a cobalt (II)-substrate complex. During the induction period, the cobalt (II) complexes are converted to cobalt (III) species via their dioxygen adducts in the presence of dioxygen and the substrate, 3-methylindole. For the steady state, a mechanism is proposed which involves a cobalt (III)-anion complex as the catalytic species; facile oxygen introduction takes place at the coordinated deprotonated substrate.View full abstractDownload PDF (811K) -
HIDEJI ITOKAWA, HAJIME MATSUMOTO, SUSUMU MIHASHI, YOISHI IITAKA, ATSUS ...1985 Volume 33 Issue 6 Pages 2204-2212
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNovel five humulenoids were isolated from Torilis scabra D.C. and their structures were determined by chemical reaction and instrumental analysis. The chiroptical method for determining the absolute configuration of allylic alcohols, reported by Harada and Nakanishi, was found to be applicable to eleven-membered-ring humulenoids.View full abstractDownload PDF (740K) -
TAISUKE ITAYA, HIROO MATSUMOTO1985 Volume 33 Issue 6 Pages 2213-2219
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS3-Methylinosine (2a) has been prepared in 28% yield by heating 5-(methylamino)-1-(2, 3, 5-tri-O-acetyl-β-D-ribofuranosyl) imidazole-4-carboxamide (5c) with a mixture of ethyl orthoformate and acetic anhydride, followed by ammonolysis. Compound 2a gave the stable 1, 2-dihydro derivative 6 in 77% yield on catalytic hydrogenation over Pd-C. The pyrimidine moiety of 2a has been shown to undergo ring cleavage under alkaline conditions at a rate three times faster than that of 3, 9-dimethylhypoxanthine (3a). The glycosidic bond of 2a is unusually susceptible to acidic hydrolysis and the rate was shown to be faster than that of inosine by a factor of 104.View full abstractDownload PDF (773K) -
YASUHIRO IMAKURA, SHIGERU KOBAYASHI, YOSHINOBU YAMAHARA, MASARU KIHARA ...1985 Volume 33 Issue 6 Pages 2220-2227
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new iridoid glucoside, campsiside, was isolated along with 5-hydroxycampsiside (pond-raneoside) and an alkaloid, boschniakine, from Campsis chinensis. The structures of campsiside and 5-hydroxycampsiside (pondraneoside) were established as 5 and 12, respectively, from chemical and spectral evidence.View full abstractDownload PDF (744K) -
KOHJI OKANO, TOSHIAKI MORIMOTO, MINORU SEKIYA1985 Volume 33 Issue 6 Pages 2228-2234
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new, general method for the synthesis of β-aminocarboxylic esters (9) and acids (10) was developed. The introduction of a primary aminomethyl unit at the α-position of carboxylic esters (2) and acids (3) was achieved in high yields by the silyl trifluoromethanesulfonate (6)-catalyzed reaction of ketene silyl acetals (4) and ketene bissilyl acetals (5) with N, N-bis (trimethylsilyl)-methoxymethylamine (1). A possible mechanism for the reaction is proposed.View full abstractDownload PDF (660K) -
TOHRU KIKUCHI, SHIGETOSHI KADOTA, HISASHI SUEHARA, TSUNEO NAMBA1985 Volume 33 Issue 6 Pages 2235-2242
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the neutral fraction of the ether extract of Nervilia purpurea SCHLECHTER (Orchidaceae), unusual side chain sterols (5a, 6a, and 7a), previously reported as the constituents of marine invertebrates, were isolated along with 24-epibrassicasterol, 24ξ-methylcholesterol, ergosterol, and stigmasterol. A new non-conventional side chain sterol, named nervisterol (8a), was also isolated and its structure was elucidated.View full abstractDownload PDF (726K) -
MOHAMMED EKRAMUL HAQUE, TOHRU KIKUCHI, KIMIHIRO YOSHIMOTO, YOSHISUKE T ...1985 Volume 33 Issue 6 Pages 2243-2255
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRegioselective monoalkylation of some pento- and hexopyranosides (Me β-L-Ara, Ph α-L-Ara, Me α-D-Xyl, Me β-D-Xyl, Me α-D-Glc, Me β-D-Glc, Me α-D-Gal, Me β-D-Gal, and Me α-D-Man) was examined by using the dibutyltin oxide method without protecting the hydroxyl groups. By this method, alkylation proceeds more or less in the same fashion as reported for acylation (through the formation of cyclic tin intermediates) and selectively activates an equatorial hydroxyl group which has an oxygenated function (OH or OMe) in a cis relationship at an adjacent position, even in the presence of a more reactive primary hydroxyl group. However, in some instances the position of activation is different. Various monoalkyl others thus prepared were identified by analyses of their carbon-13 nuclear magnetic resonance spectra.View full abstractDownload PDF (1216K) -
KAZUO OGAWA, SHOZO YAMADA, TADAFUMI TERADA, TOMIO YAMAZAKI, TAKAJI HON ...1985 Volume 33 Issue 6 Pages 2256-2265
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2-Aklylidene-4-arylidene-1, 3-oxathiolan-5-one (III-1a-m) and 2, 4-diarylidene-1, 3-oxathiolan-5-one (III-2a-i) derivatives were synthesized by treating β-aryl-α-mercaptoacrylic acids (I) with alkanoic acid anhydrides (II) or by treating α-acylthio-β-arylacrylic acids (V) with thionyl chloride in dimethylformamide. Basic hydrolysis and methanolysis of III-1 and III-2 in the presence of lithium hydroxide easily occurred to give the corresponding ring-cleaved products, the carboxylic acid (I and II) and the ester (VII and VIII), respectively. The catalytic hydrogenation of the two olefinic bonds of III-2 in the presence of 10% palladium charcoal proceeded easily without ring cleavage to give 1, 3-oxathiolan-5-one (IXa-e) derivatives. The oxidation of III-1 and III-2 with m-chloroperbenzoic acid afforded the corresponding 1, 3-oxathiolan-5-one S-oxide (Xa, b) derivatives.View full abstractDownload PDF (904K) -
KENJI MIZUTANI, KAZUHIRO OHTANI, RYOJI KASAI, OSAMU TANAKA, HIROMICHI ...1985 Volume 33 Issue 6 Pages 2266-2272
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSα-L-Rhamnosyl, α-L-arabinosyl, 2'-O-β-D-glucosyl-α-L-arabinosyl and 2'-O-α-L-rhamnosyl-α-L-arabinosyl esters of octanoic aicd and β-D-xylosyl, α-L-rhamnosyl, α-L-arabinosyl, 2'-O-β-D-glucosyl-α-L-arabinosyl and 2'-O-α-L-rhamnosyl-α-L-arabinosyl esters of 3-O-acetyloleanolic acid were synthesized. The nuclear magnetic resonance spectra of sugar moieties of the esters of 3-O-acetyloleanolic acid, which is a representative sterically hindered carboxylic acid, were compared with those of the corresponding less-hindered glycosyl esters of octanoic acid. In the case of rhamnose and arabinose, the displacements of sugar carbon signals on acylation of the anomeric hydroxyl group are similar to those already observed for fatty acid glucosyl esters regardless of the steric hindrance of the acyl group. However, the 2-O-glycosylation shifts of 1-O-acyl-α-L-arabinopyranose were found to depend upon the steric hindrance of the acyl groups. The anomalous 2'-O-glycosylation shifts of arabinosyl carbon signals of α-L-arabinosyl 3-O-acetyl-oleanolate were not observed in the case of α-L-arabinosyl octanoate.View full abstractDownload PDF (783K) -
MIYOJI HANAOKA, KAZUYOSHI NAGAMI, YURIKO HIRAI, SHUNICHIRO SAKURAI, SH ...1985 Volume 33 Issue 6 Pages 2273-2280
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBerberine (1) was transformed stereoselectively into either the trans- or cis-hydroxyspiro-benzylisoquinoline (9 or 10) via the 8, 14-cycloberbine (3). This method was applied to a first transformation of the protoberberine (22) into a spirobenzylisoquinoline alkaloid, (±)-fumaricine (6). Irradiation of the phenolbetaine (24) derived from the protoberberine (22) afforded its valence isomer, the 8, 14-cycloberbine (25), treatment of which with ethyl chloroformate gave the spirobenzylisoquinoline (26). Hydrogenolysis of 26 followed by lithium aluminum hydride reduction provided (±)-fumaricine (6). Similarly, palmatine (31) was converted via the 8, 14-cycloberbine (34) and the keto-urethane (35) into the trans-hydroxyspirobenzylisoquinoline (7), the key intermediate in a synthesis of (±)-alpinigenine (8), a rhoeadine alkaloid.View full abstractDownload PDF (936K) -
SATOSHI MORIMOTO, GENICHIRO NONAKA, ITSUO NISHIOKA, NOBUHISA EZAKI, NO ...1985 Volume 33 Issue 6 Pages 2281-2286
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeven new methyl derivatives of flavan-3-ols (compounds 1-7) and one 1, 3-diarylpropan-2-ol (compound 8) were isolated from three Lauraceous plants (1, and 3-7 from Cinnamomum cassia, 1, 3 and 4 from Cinnamomum obtusifolium, and 1-4 and 8 from Lindera umbellata var. membranacea). Their structures were characterized mainly by proton nuclear magnetic resonance (1H-NMR) examination combined with nuclear Overhauser effect (NOE) experiments as the 3'-O-methylate (1), 3', 4'-di-O-methylate (2), 5, 3'-di-O-methylate (3) and 5, 7, 3'-tri-O-methylate (4) of (-)-epicatechin, the 4'-O-methylate (5), 7, 4'-di-O-methylate (6) and 5, 7, 4'-tri-O-methylate (7) of (+)-catechin, and 1-(4', 6'-dihydroxy-2'-methoxyphenyl)-3-(4'-hydroxy-3"-methoxyphenyl)-propan-2-ol (8).View full abstractDownload PDF (703K) -
SHINICHI YOSHIMURA, HIROMI NARITA, KOJI HAYASHI, HIROSHI MITSUHASHI1985 Volume 33 Issue 6 Pages 2287-2293
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe glycosides of Dregea volubilis (L). BENTH. were further investigated. Five new glycosides named dregeosides H (1), Dp1 (2), Da1 (3), Gp1 (4), and Ga1 (5) were isolated and their structures were characterized on the basis of chemical and spectral evidence.View full abstractDownload PDF (680K) -
SACHIKO TSUKAMOTO, KOJI HAYASHI, HIROSHI MITSUHASHI1985 Volume 33 Issue 6 Pages 2294-2304
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeven new glycosides named wilfosides D1N (7), K1N (8), M1N (9), F1N (10), W1N (11), W3N (12), and G1G (13) were isolated from Cynanchum wilfordi HEMSLEY (Asclepiadaceae), and their structures were deduced on the basis of spectral and chemical evidence. A unique feature is that 7-11 and 13, as well as wilfosides C1N (2), C2N (3), C1G (5), and C2G (6), each include both D-(22) and L-cymarose (23) in the sugar chain. L-Diginose (24) is also a constituent of their sugar chains. The carbon-13 nuclear magnetic resonance (13C-NMR) chemical shifts of methyl α-(24a) and β-L-diginopyranoside (24b) were assigned, and the conformations of 24a and its acetate were studied.View full abstractDownload PDF (993K) -
TADAYUKI KURAISHI, TAKAO MURAKAMI, TAKAO TANIGUCHI, YOHKO KOBUKI, HARU ...1985 Volume 33 Issue 6 Pages 2305-2312
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the fronds of five pteridaceous ferns [Microlepia speluncae (L). MOORE, M. trapeziformis (ROXB.) KUHN, M. obtusiloba HAYATA, M. substrigosa TAGAWA and M. strigosa (THUNB.) PRESL], several 1-indanone-type sesquiterpenes (pterosins and pterosides) were isolated. Four of them, isolated from M. speluncae were new and were assigned the structures 13-hydroxy-3 (R)-pterosin D (V), 13-hydroxy-3 (R)-pterosin D 3-O-α-L-arabinopyranoside (VI), 3 (R)-pterosin D 3-O-α-L-arabinopyranoside (VIII) and 2 (R), 3 (R)-pterosin D 3-O-α-L-arabinopyranoside (XI). The structures were elucidated mainly by spectroscopic methods. Compound V was named spelosin. The investigation of two other species, M. calvescens (WALL.) PRESL and M. okamotoi TAGAWA, gave no identifiable compounds, of this type.View full abstractDownload PDF (875K) -
MASAYUKI KUZUYA, AKIHIRO NOGUCHI, SHOJI KAMIYA, TAKACHIYO OKUDA1985 Volume 33 Issue 6 Pages 2313-2322
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reactions of 1-unsubstituted 2-pyridones with benzyne afforded the Diels-Alder adduct, 5, 6-benzo-2-azabarrelen-3 (2H)-ones, together with a large amount of the Michael-type adduct, 2-phenoxypyridines.View full abstractDownload PDF (846K) -
OSAMU TANAKA, TOSHINOBU MORITA, RYOJI KASAI, JUNKO KINOUCHI, SHUICHI S ...1985 Volume 33 Issue 6 Pages 2323-2330
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSaponins of rhizomes of two specimens of Panax pseudo-ginseng subsp. himalaicus collected at high-altitude areas of Bhutan (Tzatogang and Pari-la : tentatively named specimens T and P) were investigated. With regard to oleanolic acid saponins, two new saponins, pseudo-ginsenosides-RT1 and RP1, were isolated along with the known saponins, chikusetsusaponins IVa and V, from both specimens. It seems significant that chikusetsusaponin IV was not detected in these specimens, in contrast to Japanese and Chinese P. japonicus and P. pseudo-ginseng subsp. himalaicus collected at lower-altitude areas of Bhutan, all of which contained chikusetsusaponin IV as one of the major saponins, whereas they lacked pseudo-ginsenosides-RT1 and -RP1. As regards dammaranesaponins, ginsenosides-Rb1, -Rd, -Rg1 and a new saponin, pseudo-ginsenoside-RT3, were isolated from specimen T, while ginsenosides-Rb1, -Rd, -Re, -Rg1 and -F2, gypenoside-XVII and pseudo-ginsenoside-RT3 were isolated from specimen P. Characteristic saponins having the ocotillol-type side chain were also isolated; pseudo-ginsenoside-F11 and three new saponins, pseudo-ginsenosides-RT2, -RT4 and -RT5, from specimen T and pseudo-ginsenoside-RT4 from specimen P.View full abstractDownload PDF (882K) -
KUNIO HIROI, SHUKO SATO1985 Volume 33 Issue 6 Pages 2331-2338
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe asymmetric [2, 3] sigmatropic rearrangements of 2-alkylamino-3-phenyl-2-pentenyl-methylsulfonium methylides were accomplished by the reaction of ethylphenylketenimines 3 having a chiral carbon next to the nitrogen atom with trimethylsulfonium ylide, and acidic hydrolysis of the imines 4 thus obtained led to optically active 3-methylthiomethyl-3-phenyl-2-pentanone (5). The reaction of ethylphenylketene (-)-menthylimine (3g) with trimethylsulfonium ylide at -78°C resulted in the highest optical yield of (R)-(-)-5 in the above sequence.View full abstractDownload PDF (808K) -
TAISUKE ITAYA, HIROO MATSUMOTO, TOMOKO WATANABE, TSUNEHIRO HARADA1985 Volume 33 Issue 6 Pages 2339-2347
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of 5-(methylamino)-1-β-D-ribofuranosylimidazole-4-carboxamide (5a) with CNBr in acetate buffer gave the 5-cyanomethylamino derivative 6a, which was cyclized to 3-methyl-guanosine (7) in the presence of NaOEt. Cyclocondensation of 7 with bromoacetone in the presence of K2CO3 provided 3-β-D-ribofuranosylwye (2), the most probable structure for the fluorescent nucleoside from Torulopsis utilis phenylalanine transfer ribonucleic acid (tRNAPhe). The glycosidic bonds of 2 and 7 have been shown to be unusually subject to cleavage under either acidic or basic conditions, but proved to be less labile under neutral conditions, as had been reported. The base moiety of 2 is also cleaved under basic conditions.View full abstractDownload PDF (943K) -
TOMIKI HASHIYAMA, HIROZUMI INOUE, MIKIO TAKEDA, SAKAE MURATA, TAKU NAG ...1985 Volume 33 Issue 6 Pages 2348-2358
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSStereochemical aspects of the oxirane-ring opening of methyl trans-3-(4-methoxyphenyl)-glycidate (1) with 2-nitroaniline (5) were investigated. ZnI2 showed good catalytic activity in this reaction, giving the cis-opening product (6a) predominantly. On the other hand, the reaction on the surface of silica gel proceeded predominantly by trans-opening. Silica gel had rather little effect on the reaction of 1 with 2-nitrothiophenol or 2-nitrophenol. Some 1, 5-benzodiazepine derivatives (18-21), 1-aza analogues of diltiazem, were synthesized from 6a, b for pharmacological evaluation. Some oxidative epimerization of 9a, b was observed during cyclization in boiling xylene in the presence of air. The cerebral vasodilating activity of 21a, the most potent compound in this series, was about 0.5 that of racemic diltiazem. The structure-activity relationships are discussed.View full abstractDownload PDF (1092K) -
TOSHIO TANAKA, NORIAKI OKAMURA, KIYOSHI BANNAI, ATSUO HAZATO, SATOSHI ...1985 Volume 33 Issue 6 Pages 2359-2385
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNovel 7-thiaprostaglandin E1 derivatives and congeners were synthesized by a stepwise three-component coupling process, which involves the introduction of α-side chains (thiols) and β-side chains (organocopper reagents) into (R)-4-tert-butyldimethylsilyloxy-2-cyclopentenone. Several acid derivatives of 7-thiaprostaglandin E1 were also prepared either by enzymatic or by chemical methods. The stereochemistry of these products was assigned on the basis of the results with chiral protected cyclopentenones and chiral ω-side chains. Some of these 7-thiaprostaglandin E1 congeners were found to exhibit more potent platelet aggregation-inhibitory activity than PGE1. The structure-activity relationship of these congeners is discussed.View full abstractDownload PDF (1931K) -
KAZUYUKI TOMISAWA, KAZUYA KAMEO, TOHRU MATSUNAGA, SHIUJI SAITO, KAZUAK ...1985 Volume 33 Issue 6 Pages 2386-2394
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS3-(4-Phenoxybenzoyl) propionic acids were prepared and tested for hypolipidemic activity in normal rats. A structure-activity relationship study showed that the 2-acetylthio derivative had hypolipidemic activity. Among these compounds, 2-acetylthio-[3-(4-chlorophenoxy) benzoyl] propionic acid possessed very potent activity.View full abstractDownload PDF (906K) -
MASAKO KAWASE, KEIJIRO SAMEJIMA, MASASHI OKADA, KIYOSHIGE OCHI, ISAO M ...1985 Volume 33 Issue 6 Pages 2395-2402
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDerivatives of 5-fluorouracil (5-FU) substituted at the N-1 position were synthesized in order to investigate their enzymatic conversion to N1-(2-formylethyl)-5-FU, which is expected to give 5-FU with concomitant release of acrolein. Proton nuclear magnetic resonance spectroscopic studies of authentic N1-(2-formylethyl)-5-FU suggested that the compound exists in an equilibrium mixture of free aldehyde and cyclic hemiacetal forms. Spontaneous liberation of 5-FU from N1-(2-formylethyl)-5-FU at neutral pH was demonstrated by thin-layer chromatography using both the authentic compound and N1-(3-aminopropyl)-5-FU after treatment with amine oxidase, but the release of 5-FU seemed to be limited. Cytotoxicity was observed with N1-(2-formylethyl)-5-FU and N1-(3-aminopropyl)-5-FU, but none of the derivatives of 5-FU presently prepared showed a positive effect on P388 leukemia inoculated into mice.View full abstractDownload PDF (843K) -
MITSUYO TANAKA, KAZUYOSHI HORISAKA, CHISAKO YAMAGAMI, NARAO TAKAO, TOS ...1985 Volume 33 Issue 6 Pages 2403-2410
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of aralkyl and alkyl carbamates of the type R1OCONR2R3 (R1=alkyl or aralkyl, R2, R3=H, Me, Et) were prepared and tested for anticonvulsant activity in mice by means of the maximal electroshock seizure test. The ED50 values were analyzed in terms of hydrophobic (log P), electronic (σ1) and other parameters by regression analysis. The results are essentially the same as those for previously studied m-and p-substituted benzyl N, N-dimethylcarbamates (X-C6H4-CH2OCONMe2). The activity depended parabolically on log P with an optimum log P of 1.7, and was negatively correlated with σ1. It was also found that the potency is reduced when R1 is an alkyl group or includes a hydrogen-bonding group. Structural requirements for the optimal potency and the aromatic ring contribution to the activity are discussed.View full abstractDownload PDF (645K) -
MICHINORI KUBO, HIDEAKI MATSUDA, TADATO TANI, SHIGERU ARICHI, YOSHIYUK ...1985 Volume 33 Issue 6 Pages 2411-2415
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe flavonoid components, baicalein, baicalin, wogonin, wogonin-7-O-D-glucuronide, oroxylin A, skullcapflavone II, chrysin, (2S)-2', 5, 6', 7-tetrahydroxyflavanone and (2R, 3R)-2', 3, 5, 6', 7-pentahydroxyflavanone, obtained from the roots of Scutellaria baicalensis have been screened in comparison with two standard anti-thrombic agents, aspirin and heparin, for activity in experimental models of blood platelet aggregation or conversion of fibrinogen to fibrin. Baicalein, wogonin, oroxylin A, skullcapflavone II and chrysin at a concentration of 1.0 mM inhibited collagen-induced blood platelet aggregation. Chrysin was also found to inhibit adenosine diphosphate (ADP)-induced blood platelet aggregation. In the case of arachidonic acid-induced blood platelet aggregation, baicalein and wogonin were found to have an inhibitory action. Baicalein and baicalin among the test substances inhibited the conversion of fibrinogen to fibrin induced by thrombin. The effects of baicalein and baicalin on the experimental disseminated intravascular coagulation (DIC) induced by endotoxin in rats was examined ; both compounds prevented the decrease of blood platelets and fibrinogen in DIC rats.View full abstractDownload PDF (549K) -
ISAO IKEUCHI, TAMEYUKI AMANO1985 Volume 33 Issue 6 Pages 2416-2420
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA sensitive fluorometric method using 3-aminophenol was developed to measure 4-hydroxyifosfamide, the active metabolite of the antitumor agent ifosfamide, in blood and urine. Serum and urine samples were mixed well with four volumes of citric acid-phosphate buffer (pH 3.5) to stabilize the 4-hydroxyifosfamide. After extraction with dichloromethane, the extract containing 4-hydroxyifosfamide was evaporated to dryness under reduced pressure. The residue was dissolved in distilled water, and the reagent solution of 3-aminophenol in 2N hydrochloric acid was added. After the reaction of 4-hydroxyifosfamide with 3-aminophenol, the fluorescence intensity based on the formation of 7-hydroxyquinoline in the reaction mixture was measured by fluorometry. A linear response was obtained in this assay over the ranges of 1-10 and 5-50 nmol/ml in serum and urine, respectively. Ifosfamide and related compounds such as carboxyifosfamide and ifosfamide mustard did not interfere with the assay. The present method was used to determine the amounts of 4-hydroxyifosfamide in blood plasma and urine samples from rats treated with ifosfamide.View full abstractDownload PDF (577K) -
MUTSUKO OHTA, MASATAKE IWASAKI, KEIKI KOUNO, YO UEDA1985 Volume 33 Issue 6 Pages 2421-2424
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS4-Ethylresorcinol was found to be a very sensitive color-developing reagent for the detection of ketoses, and was used to elucidate the reaction mechanism of the Seliwanoff reaction. The reaction product (I) responsible for the characteristic coloration of the Seliwanoff reaction was isolated and determined to be 2, 7-diethyl-6-hydroxy-9-(5-methyl-2-furyl)-3H-xanthen-3-one. Compound I was also isolated as crystals from the reaction mixture obtained by Kulka's modified method using 4-ethylresorcinol as the color-developing reagent.View full abstractDownload PDF (498K) -
KAZUNOBU MIURA, JUNJI KAKUCHI, SHIGEKI TSUDA, FUMIO HARADA, TOHRU UEDA1985 Volume 33 Issue 6 Pages 2425-2431
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe chemical modification of adenine moieties of mouse 5S ribosomal ribonucleic acid (RNA) was carried out with monoperphthalic acid in order to define the secondary structure of mouse 5S ribosomal RNA. The analysis of the modified 5S ribosomal RNA showed that the adenine residues at positions 11, 13 (or/and 16), 22, 23, 49, 50, 54, 55, 77, 83, 88, 90, 100, 101 and 103 were modified to adenine N-oxide residues. This result is consistent with a secondary structure of mouse 5S ribosomal RNA consisting of 5 loops and 5 helices with three bulge structures involving cytosine and adenine residues.View full abstractDownload PDF (900K) -
SHINJI OHMORI, HIDEKO NOSE1985 Volume 33 Issue 6 Pages 2432-2437
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSExposure of the dialyzed supernatant of bovine lens homogenate to ultraviolet (UV) light led to increases in its turbidity, pigmentation, and viscosity. These photochemically induced alterations of lens proteins were prevented by glutathione, cysteine and N-acetylcysteine, but not by ascorbic acid, S-(1, 2-dicarboxyethyl)-glutathione or dulcitol.View full abstractDownload PDF (741K) -
NAOHIDE KINAE, MASARU SAITO, SATOKO SAWADA, MITSUKO YAMASHITA, HIDEAKI ...1985 Volume 33 Issue 6 Pages 2438-2444
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNondialyzable melanoidins were isolated from the reaction mixtures of carbohydrates or their derivatives (such as sugars, an osone, and furfurals) with L-tryptophan in 0.1 M phosphate buffer (pH 7.0) after 4 weeks at 37°C or 1-2h at 110°C by dialyzing the mixtures against distilled water at 4°C for 24h. The melanoidins were tested for mutagenic activities toward S. typhimurium TA100 with and without nitrite treatment. None of these melanoidins was mutagenic without nitrite treatment, though the melanoidins from 3-deoxy-D-glucosone, furfural, 5-hydroxymethylfurfural, diacetyl and triose reductone were strongly mutagenic at the dose of 200μg per plate after nitrite treatment under acidic conditions. However, the melanoidins from D-xylose, D-arabinose, D-glucose, D-fructose, maltose, lactose and sucrose induced less than twice as many his+ revertant colonies as the negative control at the dose of 400μg per plate after nitrite treatment. The mutagenic activities of the products were variable depending on the reaction conditions such as reaction time and reaction temperature. Nondialyzable substances from soy sauce and bean paste also showed weak mutagenic activities after nitrite treatment.View full abstractDownload PDF (627K) -
SHINJI SOEDA, NAOMI YAMAKAWA, MASANORI OHYAMA, HIROSHI SHIMENO, ATSUO ...1985 Volume 33 Issue 6 Pages 2445-2451
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA proline endopeptidase inhibitor was purified from rat brain cytosol by ion exchange chromatography on SP-Sephadex C-25 and repeated gel filtrations on Sephadex G-50. The purified inhibitor appeared to be homogeneous on polyacrylamide gel electrophoresis with and without sodium dodecyl sulfate and displayed no multiple forms. The inhibitor showed Mr=7000 by gel filtration and by sodium dodecyl sulfate-polyacrylamide gel electrophoresis, and contained 61.6% polar amino acid residues, 3.3% aromatic amino acid residues and no tryptophan. The inhibitor was highly specific for proline endopeptidase from rat brain and hog kidney, and inhibited the enzyme competitively. It did not act on proline-specific exopeptidase such as dipeptidyl aminopeptidase IV, or on usual endopeptidases such as trypsin, elastase and plasmin, or thiol proteases such as papain and ficin.View full abstractDownload PDF (655K) -
SHOZO KOUCHIWA, MASAMI NEMOTO, SHIGERU ITAI, HIROSHI MURAYAMA, TSUNEJI ...1985 Volume 33 Issue 6 Pages 2452-2460
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSGeneral equations were derived describing the exact dissolution profile and particle number reduction rate for powders of Weibull particle size distribution under sink conditions. Several nalidixic acid (NA) powders of Weibull distribution, having mean diameter (μ), smallest diameter (r0), and largest diameter (R0) values of 400, 0, and 1000μm respectively, were prepared by varying the parameters of the Weibull distribution. By means of dissolution tests of these powders, the effects of size distribution and truncation of powders, having the same mean diameters were investigated. The results of the dissolution tests were consistent with those obtained in computer simulations, so that the derived equations were assumed to be reasonable. The dissolution rate of powders of Weibull distribution, having the same mean diameter, increased as the size distribution became narrower. Upper-end truncation had more effect on the dissolution profile of the powders than lower-end truncation.View full abstractDownload PDF (810K) -
JUN HAGINAKA, JUNKO WAKAI, HIROYUKI YASUDA, TOYOZO UNO, TERUMICHI NAKA ...1985 Volume 33 Issue 6 Pages 2461-2468
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe degradation kinetics of sodium sulbactam in various buffer solutions have been investigated over a pH range of 0.74 to 9.95 at 35°C and at an ionic strength of 0.5. The amounts of intact sodium sulbactam and a degradation product were determined by an ion-pair reversed-phase high-performance liquid chromatographic method. The degradation kinetics were consistent with a scheme in which sodium sulbactam is degraded to 2-amino-3-methyl-3-sulfinobutanoic acid and formylacetic acid via 5-carboxy-6-methyl-6-sulfino-4-aza-2-heptenoic acid, which is a labile intermediate. The observed degradation rates at various pHs followed pseudo-first-order kinetics. The pH-rate profile showed that the maximum stability of sodium sulbactam occurred in the pH range of 3.0 to 7.0, and that sodium sulbactam is much more stable than potassium clavulanate over the whole range of pH examined.View full abstractDownload PDF (688K) -
YOSHIAKI KAWASHIMA, TETSURO HANDA, AKIHIRO KASAI, HIDEO TAKENAKA, SHAN ...1985 Volume 33 Issue 6 Pages 2469-2474
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe drug release from theophylline granules coated with chitosan-sodium tripolyphosphate complex followed zero-order kinetics after an induction period, which depended on the swelling of the granules during the dissolution. The swelling was greater in the acidic medium than in the alkaline one, resulting in an increase of the drug release rate. A linear correlation between the drug release rate and the reciprocal of coating film thickness was found. By hardening the coating film with glutaraldehyde, the swelling of the granules was reduced and the drug release rate was decreased. Pre-drying of the granules prior to the hardening was fairly effective in reducing the drug release rate. It was found that the coating film became seamless after treatment with glutaraldehyde. Even when the dissolution solvent was exchanged from disintegration test solution No. 1 (pH 1.2) to No. 2 (pH 6.8), the drug release rate changed little.View full abstractDownload PDF (792K) -
HIROSHI KIWADA, HITOSHI NIIMURA, YURIKO KATO1985 Volume 33 Issue 6 Pages 2475-2482
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe tissue distribution of alkyl glycoside vesicles (AGV), which are based on synthetic alkyl glycosides, was examined after intravenous administration in mice, and the results were compared with those for phosphatidylcholine liposomes (PC liposomes). Two types of AGV were used in this study, i.e., vesicles based on stearyl galactoside (Gal-ST vesicles) and stearyl glucoside (Glu-ST vesicles). The Gal-ST vesicles showed significantly higher accumulation in the liver compared with the Glu-ST vesicles and PC liposomes, and this high accumulation was maintained for a long time (8h). On the other hand, the Gal-ST vesicles and the Glu-ST vesicles showed lower accumulation in the spleen than PC liposomes. It appears that galactoside vesicles have an affinity for the liver and the AGV intrinsically have a lower affinity for the spleen than PC liposomes. Targeting of galactoside vesicles to the liver was expected. In order to evaluate the tissue distribution profiles quantitatively, pharmacokinetic analysis of the time course data was carried out based on a physiological flow model. It has become apparent in this analysis that the affinity of the Gal-ST vesicles for the liver was as high as 1.5 times those of Glu-ST vesicles and PC liposomes, while those of Gal-ST vesicles and Glu-ST vesicles for the spleen were about a half of that of PC liposomes. It also appears that the degradation rate of these vesicles in the tissues differs with different types of vesicles. Such an analysis leading to quantitative evaluation of the targeting efficiency should be useful for developing vesicles as drug carriers.View full abstractDownload PDF (785K) -
JUN WATANABE, SATOSHI MIZUNO, KIKUO IWAMOTO, SHOJI OZEKI1985 Volume 33 Issue 6 Pages 2483-2489
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of passage through the main mandibular excretory duct on salivary excretion of urea was investigated using anesthetized dogs. Two kinds of mandibular saliva (pre-ductal saliva and post-ductal saliva) were collected from individual dogs. Pre-ductal and post-ductal mandibular saliva samples were collected individually via cannula tubing before and after flowing through the main mandibular excretory duct, respectively. Sublingual saliva was also collected to evaluate the effect of saliva passage through the non-striated duct. Salivation was evoked by electric nerve stimulation. The findings were as follows. (1) There was no significant difference between saliva/plasma concentration ratios (S/P ratios) of urea in the two mandibular salivas. (2) Salivary clearance of urea was not altered by the passage of saliva through the main mandibular excretory duct. (3) In this duct, sodium ion was slightly reabsorbed, but the S/P ratio of potassium ion was almost constant. Therefore, apparent water reabsorption may not take place in this duct. (4) From these results, it was concluded that the main mandibular excretory duct of the dog has no influence on salivary excretion of urea. (5) The mean S/P ratio of urea in sublingual saliva (1.25) was much higher than in mandibular saliva (0.330 to 0.345). Therefore, it is considered that urea might be either reabsorbed or diluted in the striated duct.View full abstractDownload PDF (681K) -
SHOZO MIYAZAKI, SHIGEMI TAKEUCHI, WEIMIN HOU, NORIO HASHIGUCHI, CHIZUK ...1985 Volume 33 Issue 6 Pages 2490-2498
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEthylene-vinyl alcohol (EVAI) copolymer was evaluated as a vehicle for controlled or sustained release of 5-fluorouracil (5-FU) and adriamycin. The variation of initial drug concentration and, to an even greater extent, the variation in comonomer ratio affected the drug release rate as well as the cumulative amount of the drug released. An increase in the ethylene content of the EVAI copolymer decreased drug release. It appears that EVAI copolymer can be used as a membrane for controlling the release of 5-FU or adriamycin. The antitumor activity of EVAI copolymer matrices containing these anticancer agents was evaluated against Ehrlich ascites carcinoma (EAC) in mice on the basis of changes in body weight and animal survival data. Tumor cell injections were performed on day 0 and matrix implantations on day 3, both intraperitoneally. The suppressive effect of matrices containing anticancer agents on the increase in body weight was higher than that of the free drugs. A prolongation of the life span of tumor-bearing mice following implantation of therapeutic matrices was also noted. Implantation of the EVAI copolymer matrix containing an anticancer agent was less effective against the P388 leukemia than the EAC. These results suggest that EVAI copolymer matrices containing anticancer agents may be effective in cancer chemotherapy. Matrices composed of EVAI copolymer could be useful vehicles for implanted delivery systems for anticancer agents.View full abstractDownload PDF (855K) -
MAMORU OHASHI, ROBERT P. BARRON, WALTER R. BENSON1985 Volume 33 Issue 6 Pages 2499-2506
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn-beam electron ionization (EI) and mass analyzed ion kinetic energy (MIKE) spectrometric techniques were used to study the EI-induced fragmentation of choline iodide, choline chloride, hexadecyltrimethylammonium bromide, ethylhexadecyldimethylammonium bromide, and methyltricaprylammonium chloride. The in-beam EI and MIKE spectra of these compounds are presented. The in-beam EI spectra exhibit intact quaternary ammonium cations as well as thermally and EI-induced fragment ions. The fragmentation pathways arising from the intact cations in the in-beam EI spectra were defined by using the MIKE technique. The general fragmentation processes are similar to those of simple tetraalkylammonium cations previously reported. The inbeam EI spectra of a sample of tricaprylmethylammonium chloride exhibit abundant ions that are due to lower and higher homologous cations, indicating that the sample is a mixture of at least three homologs.View full abstractDownload PDF (640K) -
JUNZO SUZUKI, TOSHIYUKI SATO, SHIZUO SUZUKI1985 Volume 33 Issue 6 Pages 2507-2515
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the photoreaction products of biphenyl in aqueous nitrate solution, the following eight hydroxynitrobiphenyls were isolated by silica gel column chromatography and thin layer chromatography on silica gel and polyamide plates : 4-hydroxy-3, 5-dinitrobiphenyl (F1 (2) or), 4, 2'-dihydroxy-3, 3'-dinitrobiphenyl (F4 (1)-3), 4-hydroxy-3, 3'-dinitrobiphenyl (F4 (1)-4), a hydroxy-dinitrobiphenyl (F4 (1)-5a), 4, 4'-dihydroxy-3, 3'-dinitrobiphenyl (F4 (1)-5b), a dihydroxydinitrobiphenyl (F4 (1)-6), 2-hydroxy-3-nitrobiphenyl (F5 (1)) and 4-hydroxy-3-nitrobiphenyl (F5 (2)). Among these compounds, four dinitro compounds, F1 (2) or, F4 (1)-4, F4 (1)-5a and F4 (1)-6, exhibited mutagenicity toward S. typhimurium TA 98 without S-9 mix. The major products in this reaction were nitrophenylphenols, F5 (1) and F5 (2), and these were non-mutagenic. The major mutagens, F4 (1)-5a and F4 (1)-6, were produced in such small amounts that the exact structures could not be determined. The mechanism of production of these hydroxynitrobiphenyls is discussed on the basis of the results of analysis of the reaction mixture by high-performance liquid chromatography.View full abstractDownload PDF (784K) -
MIEKO IITSUKA, TOSHIHIDE HOSHINO, TETSUTA KATO, KIYOMI KIKUGAWA1985 Volume 33 Issue 6 Pages 2516-2521
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFormation of N-nitrosodimethylamine and N-nitrosodiethylamine in organic solvents such as chloroform, benzene, ethyl acetate, n-hexane, acetonitrile and dioxane was much faster than that in the control citrate buffer at pH 3. This effect of the organic solvents may be due to their ability to suppress ionization of nitrous acid. Formation of the nitrosamines in acetone was faster, but the yield was less than in other organic solvents, probably due to reaction of the solvent with nitrous acid. Ethyl alcohol was not useful as the control buffer, since it consumed nitrous acid to produce nitrite ester. The use of pH-controlled aqueous systems containing acetonitrile and dioxane accelerated the formation of the nitrosamines by increasing the concentration of nitrous acid ; the 25% acetonitrile-containing system produced 3 times as much N-nitrosodimethylamine and 6 times as much N-nitrosodiethylamine as compared to the control citrate buffer at pH 4. Formation of the nitrosamines in citrate was accelerated or inhibited by addition of acetone and ethyl alcohol depending upon the pH conditions. It is concluded that most organic solvents suppressed the ionization of nitrous acid and accelerated the nitrosation of the secondary amines.View full abstractDownload PDF (628K) -
JUZIRO NISHIJO, NORIKO MORITA1985 Volume 33 Issue 6 Pages 2522-2524
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe interaction of theophylline and bovine serum albumin (BSA) was investigated by using the equilibrium dialysis method. The experiments were carried out at 5°C and at pH 6.85 using 1/15 M phosphate buffer. The binding parameters determined are as follows ; n1=0.48, n2=1.34, K1=2.89×103 M-1, and K2=4.03×102M-1. The interaction of aminophylline with BSA was also investigated in the same manner. The binding parameters are as follows ; n1=0.43, n2=1.29, K1=2.74×103M-1, and K2=5.61×102M-1. These parameters are calculated on the basis of theophylline content in aminophylline, which is a 2 : 1 complex of theophylline with ethylenediamine. There was little difference in binding parameters between theophylline and aminophylline. This is to be expected in view of the findings that under the experimental conditions used, theophylline does not interact significantly with ethylenediamine, and the latter shows essentially no interaction with BSA.View full abstractDownload PDF (409K) -
MAGOICHI SAKO, YUTAKA KOJIMA, KOSAKU HIROTA, YOSHIFUMI MAKI1985 Volume 33 Issue 6 Pages 2525-2528
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of 6-(N-methylanilino)-5-(N-phenylimino) pyrimidine-2, 4 (3H, 5H)-dione (2a) with benzyl hydrosulfide or benzylamine under mild conditions without any catalyst resulted in the concurrent occurrence of a redox reaction and nucleophilic substitution at the C (6)-position of 2a to give 5-anilino-6-(N-methylanilino) uracil (1a), 6-substituted 5-(N-phenylimino) pyrimidine-2, 4 (3H, 5H)-diones (2b, c), and the oxidation product (dibenzyl disulfide or N-benzylidenebenzylamine). The substitution products 2b, c also oxidized benzyl hydrosulfide and benzylamine under the same conditions.View full abstractDownload PDF (550K) -
EMI OKUYAMA, MIKIO YAMAZAKI1985 Volume 33 Issue 6 Pages 2529-2530
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe efficient large-scale preparation of cerebroside, which has interesting pharmacological effects, from crude soya lecithin (7.29 g crude and 6.8 g pure cerebroside from 1 kg of soya lecithin), was achieved by the application of high-performance liquid chromatography using watercontaining silica gel.View full abstractDownload PDF (372K) -
YUKIO MASAKI, KAZUHIKO SAKUMA, KENJI KAJI1985 Volume 33 Issue 6 Pages 2531-2534
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe Mislow-Evans rearrangement of α, β-and α, γ-disubstituted allylic sulfoxides (2) to (E)-allylic alcohols (4) was found to occur under acidic conditions. By combination of this method with a catalytic oxidation of allylic sulfides (1), a novel one-pot transformation of allylic sulfides (1) to 4 was achieved.View full abstractDownload PDF (494K) -
ANAMARIA CUADRO, JOSE ELGUERO, PILAR NAVARRO1985 Volume 33 Issue 6 Pages 2535-2540
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom 3, 3', 5, 5'-tetramethyl-4, 4'-bis-1 H-pyrazole, 3, 3', 5, 5'-tetramethyl-4, 4'-methylenebis-1 H-pyrazole and 4, 4'-methylenebis-1 H-pyrazole, the corresponding 1, 1'-dibenzyl and 1, 1'-dihydroxymethyl derivatives have been obtained. Benzylation of 1H-bispyrazoles was carried out by treatment with benzyl chloride under phase transfer conditions. Hydroxymethylation was done by treatment with 37% aqueous formaldehyde either in acidic or in neutral medium. All the products obtained have been evaluated as cytotoxic, and 1, 1'-dibenzyl-3, 3', 5, 5'-tetramethyl-4, 4'-bispyrazole is a powerful cytotoxic agent (ED50=7 μM).View full abstractDownload PDF (604K) -
HIROTERU SAYO, TAKASHI MICHIDA1985 Volume 33 Issue 6 Pages 2541-2544
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCation radicals generated by anodic oxidation of N-(o-nitrophenylthio) alicyclic amines (morpholine (1), thiomorpholine (tetrahydro-4H-1, 4-thiazine) (2), piperidine (3), pyrrolidine (4)) in acetonitrile were studied by cyclic voltammetry (CV) and electron spin resonance spectroscopy (ESR). 2-(o-Nitrophenylthio) indan-l-ol (6) was obtained from the solution after controlled potential electrolysis (CPE) of 1-3 in acetonitrile containing indene (5) and 0.1 M NaClO4 at a glassy carbon anode. The cation radicals produced by CPE of 1-3 attacked 5 to give 6 as a final product.View full abstractDownload PDF (476K) -
KAZUYOSHI TAKEDA, KANOKO TSUBOYAMA, AKIRA SUZUKI, HARUO OGURA1985 Volume 33 Issue 6 Pages 2545-2548
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe enantioselective coupling reaction of N-protected amino acid (+)-N-hydroxycamphorimide esters (-OCamp) with racemic amino acid esters is discussed. The coupling reaction of several amino acids showed high enantioselectivity.View full abstractDownload PDF (481K) -
TOSHIKAZU SUZUKI, YOSHIMASA HASHIMURA, SHIGEYUKI TAKEYAMA1985 Volume 33 Issue 6 Pages 2549-2552
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEight urinary metabolites of the positive inotropic agent denopamine, (-)-(R)-1-(p-hydroxyphenyl)-2-[(3, 4-dimethoxyphenethyl) amino] ethanol, in man were separated and identified by capillary column gas chromatography-mass spectrometry. The metabolites were products of oxidative 3'-or 4'-O-demethylation and/or meta-hydroxylation followed by meta-or para-catechol O-methyltransferase-methylation. Separation of the four isomers of 1-(hydroxymethoxyphenyl)-2-[(hydroxymethoxyphenethyl) amino] ethanol was made possible by the use of a capillary column.View full abstractDownload PDF (468K) -
ISAO IKEUCHI, TAMEYUKI AMANO1985 Volume 33 Issue 6 Pages 2553-2555
Published: June 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn isotachophoretic assay method was developed for sodium mercaptoundecahydrododecaborate (1), Na210 B12H11SH, which is used for boron neutron-capture therapy. The method is simple, specific and suitable for the determination of 1 as an anion in human serum and urine. Compound 1 was separated from serum and urine constituents with 0.01 M hydrochloric acid and β-alanine (leading electrolyte, pH 3.70) and 0.01 M n-caproic acid (terminating electrolyte). The recoveries of 1 from serum and urine were about 85 and 101%, respectively. The detection limit was 7×10-7 mol/ml in serum and urine. The procedure could also detect the oxidation product, sodium di (thioundecahydrododecaborate), at 5×10-7 mol/ml or more in urine. The present method was used to determine the levels of 1 in urine samples of patients with malignant brain tumor being treated by boron neutron-capture therapy.View full abstractDownload PDF (415K)