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Volume 41, Issue 2
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Yong-Zhong DA, Junko YANAGI, Kyoko TANAKA, Hideaki FUJIWARA1993 Volume 41 Issue 2 Pages 227-230
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs an extension of our recent studies on the relationships between thermochemical aspects of partition and biological activities, enthalpies and entropies of partition have been determined for 17 congeners of the titled quaternary ammonium chlorides, and the novel hydrophobic parameters, PH and PS, have been assigned. The regression equations using these parameters are discussed against the biological activities of pasteurization : a parabolic model is built up with regard to the PH and PS terms, which gives an improved result compared to a linear model.View full abstractDownload PDF (648K) -
Yayoi KAFUKU, Junko OHNISHI, Mitsunobu DOI, Masatoshi INOUE, Toshimasa ...1993 Volume 41 Issue 2 Pages 231-234
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs part of the designs of tryptophan-containing peptides which possess specific binding ability for each nucleic acid base, a series of N-acetylTrp-(Gly)m-Asp-(Gly)n-TrpNHCH3 (m=0-2, n=0-2) were chemically synthesized, and their abilities to form complexes with a guanine base were examined by the fluorescence and 1H-NMR methods. Fluorescence titration suggested the most preferential stacking interaction of the Trp-Gly-Asp-Trp sequence with the base. Analysis of low-field shifts of guanine N2-amino protons showed the hydrogen bond pairing with the Asp carboxyl side chain and its favorable formation for the -Gly-Asp-Trp peptide sequence. On the other hand, the largest up-field shift of guanine H8 proton was observed for Trp-Gly-Asp-Trp peptide, although its shifting degree caused by the stacking interaction with the Trp indole ring was not so significant. Thus, both spectroscopic methods indicated the Trp-Gly-Asp-Trp sequence to be most suitable for the guanine base recognition, which is constituted with the intimate cooperation of the hydrogen bond formation between the Asp carboxyl and guanine NH2 groups and the stacking interaction of the base with two neighboring Trp indole rings. This sequence preference would also be possible in acidic circumstances where the guanine N7 atom is protonated. A tentative interaction model is proposed based on these spectroscopic results.View full abstractDownload PDF (663K) -
Takashi ISHIZU, Ayumi FUJII, Shunsaku NOGUCHI1993 Volume 41 Issue 2 Pages 235-238
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAnalyses of the 1H- and 13C-nuclear magnetic resonance (1H- and 13C-NMR) spectra of the cyclooctapeptide cyclo (L-Phe-L-Pro-Gly-L-Pro)2 (3) in CDCl3 with the aid of the C-H correlated spectroscopy (C-H COSY) two-dimensional NMR spectrum (Fig. 2) suggested that two kinds of C2-symmetric conformation with all trans and cis-trans-trans-trans forms coexist. When 0.5 eq of CsSCN or 1 eq of D- and L-PheOMe·HCl (D/L ratio=1/2) was added to a solution of the cyclooctapeptide (3) in CDCl3, the 1H- and 13C-NMR spectra (Fig. 3) suggested the presence of only one C2-symmetric conformation (all trans), resulting from the formation of complexes with CsSCN or D- and L-PheOMe·HCl. The 13C-NMR spectra of the complexes of the cyclooctapeptide (3 or 4) with D- and L-PheOMe·HCl displayed separate resonances for each carbon atom of D-PheOMe·HCl and L-PheOMe·HCl. Furthermore, the ability of 3 to distinguish the D from the L enantiomer, is superior to that of 4 (Table II).View full abstractDownload PDF (619K) -
Kazue OHKURA, Nobuhiko KANAZASHI, Koh-ichi SEKI1993 Volume 41 Issue 2 Pages 239-243
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhotoreaction of 6-chloro-1, 3-dimethyluracil in benzene and monosubstituted benzenes furnished cycloaddition products, cyclooctapyrimidine-2, 4-dione derivatives, in the presence of trifluoroacetic acid.View full abstractDownload PDF (724K) -
Toshio SUZUKI, Etsuko SATO, Katsuo UNNO1993 Volume 41 Issue 2 Pages 244-247
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEnantioselective syntheses of both (20R)- and (20S)-de-AB-cholesta-8(14), 22-dien-9-one (22 and 23), which are potential intermediates leading to vitamin D3, steroids and their analogues, have been developed. The (3R)-methyl-cyclopentanone 12 was obtained through a known procedure starting with (S)-2, 3-O-isopropylideneglyceraldehyde (8) or through inversion of the C6 position in compound 5 using the Mitsunobu reaction followed by orthoester Claisen rearrangement. The construction of the trans-angularly methylated CD ring was accomplished through stereo- and regioselective Michael addition of the lithium enolate of 12 to α-silylated vinyl ketone, followed by intramolecular aldol condensation.View full abstractDownload PDF (699K) -
Koichi MACHIDA, Masao KIKUCHI1993 Volume 41 Issue 2 Pages 248-251
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour new phenolic glycosides, umbelliferone 6-O-trans-caffeoyl-β-D-glucopyranoside, p-hydroxyphenyl 4-O-trans-caffeoyl-β-D-glucopyranoside, p-hydroxyphenyl 2-O-cis-p-coumaroyl-β-D-glucopyranoside and p-hydroxyphenyl 6-O-cis-p-coumaroyl-β-D-glucopyranoside, and five known compounds were isolated from the leaves of Viburnum wrightii MIQ.View full abstractDownload PDF (674K) -
Taisuke ITAYA, Takehiko IIDA, Shigeyuki SHIMIZU, Akemi MIZUTANI, Masat ...1993 Volume 41 Issue 2 Pages 252-261
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS(R)-[2-Carboxy-2-[(methoxycarbonyl)amino]ethyl]triphenylphosphonium chloride (1) was converted by treatment with anion exchange resin (HCO-3) into the inner salt 13h, which gave a better yield (43%) than 1 in the Wittig reaction with benzaldehyde to afford the [S-(E)]-(2-phenylvinyl)glycine derivative 24. The inner salt 13i bearing an N-benzyloxycarbonyl group was prepared by hydrogenolysis of (R)-[3-benzyloxy-2-[(benzyloxycarbonyl)amino]-3-oxopropyl]triphenylphosphonium chloride (11e) over palladium on carbon, followed by dehydrochlorination. Hydrogenolysis of 11e over Pearlman's catalyst afforded the unprotected phosphonium chloride 12 (X=Cl). N-tert-Butoxycarbonylation of 12 followed by dehydrochlorination afforded 13j, which was more efficiently prepared through hydrogenolysis of (R)-[3-benzyloxy-2-[(tert-butoxycarbonyl)amino]-3-oxopropyl]triphenylphosphonium chloride (11f).The usefulness of 13h-j as building blocks for the synthesis of configurationally labile (2-arylvinyl)glycine derivatives was exemplified by the Wittig reactions with piperonal, which exclusively afforded the (E)-isomers 18h-j with high optical purity in 28-39% yield.View full abstractDownload PDF (1686K) -
Kenji SHIOJIMA, Yoko ARAI, Toshio KASAMA, Hiroyuki AGETA1993 Volume 41 Issue 2 Pages 262-267
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFive new triterpenoids, filicenol A (1), filicenol B (2), isoadiantol B (3), hakonanediol (4) and epihakonanediol (5), were isolated from the leaves of Adiantum monochlamys EATON, and their structures were elucidated on the basis of spectral data and chemical correlations with known compounds. Additional data are presented for previously reported compounds (6-21) from the same source.View full abstractDownload PDF (875K) -
Kenji SHIOJIMA, Yusho SASAKI, Hiroyuki AGETA1993 Volume 41 Issue 2 Pages 268-271
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new triterpenoids, 23-hydroxyfernene (1), glaucanol A (2) and filicenoic acid (3), were isolated from the leaves of Adiantum pedatum L., and their structures were elucidated on the basis of spectral data and chemical correlations with known compounds. Additional data are presented for previously reported compounds (4-15) and the isolation and identification of six known compounds (16-21) from the same source are also described.View full abstractDownload PDF (707K) -
Nobuko SAKURAI, Masahiro NAGAI, Teruo GOTO, Takao INOUE, Pei-Gen XIAO1993 Volume 41 Issue 2 Pages 272-275
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new triterpenol xyloside, beesioside I was isolated from the rhizomes of Beesia calthaefolia, and the structure was elucidated as (20S, 24S)-15β, 16β-diacetoxy-18, 24;20, 24-diepoxy-9, 19-cyclolanostane-3β, 25-diol 3-O-β-D-xylopyranoside on the basis of chemical and physicochemical evidence, including nuclear Overhauser effect spectroscopy experiment.View full abstractDownload PDF (561K) -
Masazumi IKEDA, Masahiko OKANO, Keigo KOSAKA, Masaru KIDO, Hiroyuki IS ...1993 Volume 41 Issue 2 Pages 276-281
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA stereoselective total synthesis of (±)-cephalotaxine (1) has been achieved. Palladium-catalyzed [3+2] cycloaddition of 2-(trimethylsilylmethyl)-2-propenyl acetate to the nitrostyrene 7 gave the methylenecyclopentane 6, which was converted into the α-sulfinylacetamide 19. Treatment of 19 either with trifluoroacetic anhydride in dichloromethane at room temperature or with p-toluenesulfonic acid in boiling 1, 2-dichloroethane gave the benzazepinone 20 in good yield, and this was transformed to (±)-1 via Hanaoka's key intermediate 4.View full abstractDownload PDF (983K) -
Masayuki SHIMAGAKI, Hiroaki MUNESHIMA, Masahide KUBOTA, Takeshi OISHI1993 Volume 41 Issue 2 Pages 282-286
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSChemoenzymatic formation of 8 from an aldehyde 5 and dihydroxyacetone phosphate 6 was achieved by the use of fructose 1, 6-diphosphate aldolase as a catalyst. Transformation of 8 to 20, corresponding to pentamycin C-11-C-16 fragment, was accomplished via 18a and 18b by chemical processes.View full abstractDownload PDF (902K) -
Tomohiko KAWATE, Masako NAKAGAWA, Hitoshi YAMAZAKI, Mariko HIRAYAMA, T ...1993 Volume 41 Issue 2 Pages 287-291
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new general procedure for the alkylation of the C=N double bond of 3, 4-dihydro-β-carboline has been developed with amphiphilic reaction systems such as BF3·OEt2/RLi, RMgX, R2CuLi or trimethylsilyl trifluoromethane-sulfonate/RLi, RMgX to give the corresponding 1-substituted-1, 2, 3, 4-tetrahydro-β-carbolines.View full abstractDownload PDF (897K) -
Takashi MORI, Tomofumi SANTA, Tsunehiko HIGUCHI, Tadahiko MASHINO, Mas ...1993 Volume 41 Issue 2 Pages 292-295
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOxygenation of olefin, N-dealkylation of tertiary amine, oxidation of sulfide, and oxidative cleavage of ether bond were conducted with tetraphenylporphyrinatoiron(III) (Fe3+TPPCl), NaBH4, Me4N·OH, and molecular dioxygen in benzene-methanol solution. Fe3+TPPCl, NaBH4, and molecular dioxygen were essential for these reactions and the yields were decreased when Me4N·OH was absent. Olefins were converted to alcohols, which were not produced from the corresponding epoxides under the same conditions. In styrene oxygenation, an electron-donating substituent on the substrate decreased the reactivity, whereas in N, N-dimethylaniline demethylation, it enhanced the reactivity. Despite the use of the same reagents, the key intermediates of these two reactions are different. Fe2+TPP-σ-alkyl complexes produced from Fe3+TPPCl, olefin, and NaBH4 were identified as intermediates under anaerobic conditions. Fe2+TPP-σ-alkyl complex reacted with molecular dioxygen to give oxygenated products.Examination of the relative reactivities of p-substituted N, N-dimethylanilines in the NaBH4 reaction system revealed first, that the demethylation proceeded via one-electron abstraction, and second, that the reactive species of the demethylation reactions seems to be an iron-oxenoid.View full abstractDownload PDF (632K) -
Shigeki SASAKI, Futoshi TAKAO, Kiyoko WATANABE, Norihiro OBANA, Minoru ...1993 Volume 41 Issue 2 Pages 296-300
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNew fluorinated ligands with N-[(1-ethyl-2-pyrrolidinyl)methyl]-2, 3-dihydrobenzofuran-7-carboxamide skeleton, which are useful as a prototype to develop 18F labelled in vivo radiotracer for positron emission tomography (PET), were synthesized, and their binding affinities for the dopamine D2 receptors were investigated. Fluorine atom was introduced at C-4 of the pyrrolidine ring (10) or at ethyl substituent at C-5 of the dihydrobenzofuran moiety (20). The in vitro IC50 values of these ligands for the dopamine D2 receptors which were determined by their ability to inhibit the binding of [3H]spiperone binding in rat striatal membrane were 17 and 36 nM, respectively. Thus, the fluorinated compounds 10 and 20 may be possible candidates for further in vivo investigation.View full abstractDownload PDF (941K) -
Kiyoshi TANIGUCHI, Shinji SHIGENAGA, Takatomo OGAHARA, Takashi FUJITSU ...1993 Volume 41 Issue 2 Pages 301-309
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2-Amino-1H-benzimidazoles (3) and 1, 2-dihydro-2-iminocycloheptimidazoles (4) were synthesized and evaluated for antiinflammatory and analgesic activities. The compounds in the series 3 were synthesized via phenylthioureas (6) or 2-chloro-1H-benzimidazole (12). Most of 4 were synthesized by two methods. One was the reaction of carbodiimides (14) with 2-amino-2, 4, 6-cycloheptatrien-1-one (method A). The other was the reaction of guanidines (15) with 2-chloro-2, 4, 6-cycloheptatrien-1-one (method B). Some of the compounds 3 and 4 exhibited potent antiinflammatory and analgesic activities when compared to timegadine (1) or tiaramide hydrochloride (HCl) (17). It was of interest that 1-(2-benzothiazolyl)-2-cyclohexylimino-1, 2-dihydrocycloheptimidazole (4e) showed superior analgesic activity to timegadine or tiaramide HCl (ED50=1.7 mg/kg p.o. in the acetic acid-induced writhing test, ED30=14.0 mg/kg p.o. in Randall-Selitto method) in spite of no effect on prostaglandin E2 synthesis.View full abstractDownload PDF (1154K) -
Seigo SAWADA, Takashi YAEGASHI, Tomio FURUTA, Teruo YOKOKURA, Tadashi ...1993 Volume 41 Issue 2 Pages 310-313
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS7-Ethylcamptothecin (1d), a model which does not have any site on the A-ring for further modification was converted into water-soluble derivatives by opening the E-ring lactone. 1d was heated in N, N-dimethylenediamine to yield amide 2a, and this was then acylated to furnish 3a-q, which were soluble in water as their HCl salts. The propionyl (3b), butyryl (3c) and methylthiopropionyl (3h) derivatives showed higher activity than the sodium salt of 1d. The acyl group makes the derivatives more lipophilic, and ease of hydrolysis of amide 2a to 1d is thought to be necessary for significant activity.View full abstractDownload PDF (660K) -
Kouichi KASAI, Riichiro UCHIDA, Nobuyuki YAMAJI1993 Volume 41 Issue 2 Pages 314-318
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree novel N-acetyl-β-D-glucosaminides, 2', 7'-dichlorofluorescein mono(N-acetyl-β-D-glucosaminide) (6a), fluorescein mono(N-acetyl-β-D-glucosaminide) (6b) and 2', 7'-dichlorofluorescein di(N-acetyl-β-D-glucosaminide) (7a), were synthesized by the introduction of N-acetyl-β-D-glucosaminyl group into fluorescein derivatives followed by the removal of the protecting group. Compounds 6a, 6b and 7a were hydrolyzed by N-acetyl-β-D-glucosaminidase to give products showing high absorbance at a long absorption wavelength (500, 465 and 485 nm) under weakly acidic rate-assay conditions (pH 5.0). The Km values for 6a and 7a were 0.56 and 0.86 mM, respectively. Among these compounds, 7a is considered to be the most potential chromogenic substrate for the rate-assay of N-acetyl-β-D-glucosaminidase, since it gives a clear color generation from colorless to orange color (λmax 280→485 nm) by enzyme hydrolysis and has a higher water solubility of more than 30 mM.View full abstractDownload PDF (849K) -
Margarita PAGOU, Antonios KOUTSELINIS1993 Volume 41 Issue 2 Pages 319-324
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe Rm values of 32 compounds, derivatives of benzoic acid, were determined by reversed-phase thin layer chromatography (RP-TLC). The logarithm of the capacity factor, log k', of the same compounds was studied with reversed-phase high performance liquid chromatography (RP-HPLC). The lipophilicity was calculated according to the fragmental methods of Rekker and of Leo-Hansch and was compared with the experimental values of Rm and the log k'. The comparison shows that the Rekker method gives a better description of lipophilicity than that of the Leo-Hansch method.View full abstractDownload PDF (804K) -
Keiko SASAKI, Hirofumi SUZUKI, Hiroshi NAKAGAWA1993 Volume 41 Issue 2 Pages 325-328
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTrazodone hydrochloride tetrahydrate was isolated and characterized by moisture absorption equilibrium, Karl Fischer method, powder X-ray diffractometry, infrared (IR) spectroscopy and elementary analysis. Trazodone hydrochloride (anhydrate) showed a supersaturation phenomenon in the dissolution process in water. In water and under high humidity condition (>93% relative humidity), trazodone hydrochloride was converted into the hydrate (trazodone hydrochloride : H2O=1 : 4). The hydrate dehydrated under less than 51% relative humidity at 25°C. The activation energy for dehydration reaction from the hydrate to the anhydrate determined by a non-isothermal method (Ozawa method) was 37.1 kcal/mol.View full abstractDownload PDF (517K) -
Shinji NARISAWA, Hiroyuki YOSHINO, Yoshiyuki HIRAKAWA, Kazuo NODA1993 Volume 41 Issue 2 Pages 329-334
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn an attempt to develop a new simple porous film coating technique for oral controlled release dosage forms, the pore formation of ethylcellulose (EC) in the casting process was investigated. When an EC-ethanol-water ternary mixture was cast, the porous film was spontaneously formed via the processes of coacervation and gelation of the polymer. The visual and microscopic observations revealed that pore formation proceeded on the basis of the phase separation mechanism, in which ethanol and water acted respectively as a solvent and a non-solvent for the polymer. Gelation, which is an important process for determining the density of the resultant film, occurred during evaporation when the decreasing ethanol concentration reached the critical concentration of about 62%. This value was almost constant irrespective of polymer concentration and molecular weight. The density of porous EC film was changed by formulation variables of the casting solution, such as ethanol or polymer concentration and organic solvent species. The permeation study of porous EC films was conducted using salicylic acid as the permeant. The permeability of salicylic acid was changed according to the film density; that is, the permeability coefficient exponentially increased with a decrease in film density, suggesting that the drug permeability of the cast film can be modified by controlling film density.View full abstractDownload PDF (1137K) -
Katsu NAKAMORI, Ikuo KOYAMA, Tomomi NAKAMURA, Masami NEMOTO, Tsuguchik ...1993 Volume 41 Issue 2 Pages 335-338
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSQuantitative evaluation of the effectiveness of taurine against ocular surface damage caused by hypochlorous acid (HOCl) was investigated using albino rabbits. The activity of lactate dehydrogenase (LDH) released from ocular tissues into meniscus tears at eye irritation was used as an index of ocular surface damage. Instead of collecting meniscus tears directly with a glass micropipette, a new sampling method, where 150 μl of saline was instilled into the cul-de-sac of rabbit eyes and collected all of the diluted tears within 10s, was developed.The LDH activity after serial instillations of HOCl increased dose-dependently with increasing HOCl concentration. After serial instillation of taurine, HOCl was instilled in the same way. Pre-application of taurine effectively suppressed (p<0.01, n=11) the HOCl-induced LDH release as compared to saline, suggesting that the residual taurine in ocular surface tissues was still effective in protecting the tissues against HOCl by scavenging HOCl. LDH activity at 30 min after post-application of taurine was significantly lower (p<0.01, n=10) than that in the case of saline. This result indicates that taurine is effective in protecting the ocular surface after it has been attacked by HOCl. LDH activity in meniscus tears became a good index of quantitatively estimating ocular surface damage due to HOCl by devising the new sampling method. By using this method, we were able to prove objectively and quantitatively that taurine is effective in protecting the ocular surface against HOCl. It was suggested that taurine is clinically useful in the treatment of ocular surface damage caused by oxidants, such as HOCl.View full abstractDownload PDF (666K) -
Chuzo IWATA, Naoyoshi MAEZAKI, Kohji HATTORI, Masahiro FUJITA, Yasunor ...1993 Volume 41 Issue 2 Pages 339-345
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA dioxaspiro compound (4), a common intermediate for the synthesis of talaromycin A (1) and (-)-talaromycin B (2), was synthesized by two routes utilizing two kinds of asymmetric recognition of prochiral 1, 3-diols controlled by sulfinyl chirality, that is, firstly by acid promoted diastereoselective C-O bond fission of the bicyclic acetal (7) to give the dihydropyran derivative (6), which has an S-hydroxymethyl group at the C3-position (7→6), and secondly by diastereoselective intramolecular Michael addition of the diol (5), in which the three chiral centers at C5, C6, C9 were constructed in one step (5→4).View full abstractDownload PDF (1096K) -
Toru HAKATA, Masao IIJIMA, Toshio OKABE, Shigeo KIMURA, Hiroshi SATO, ...1993 Volume 41 Issue 2 Pages 346-350
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo different test methods were studied for the evaluation of release profiles of carbon dioxide, CO2, from effervescent suppositories. Three lots of commercial suppositories containing sodium bicarbonate and anhydrous sodium dihydrogen phosphate were used. The volume of CO2 released from these suppositories in normal saline with or without polysorbate 80 as a medium was measured with a gas burette.In the measurement performed using the apparatus without stirring, method 1, only 60% of CO2 was released from the suppositories in the medium without polysorbate 80. In this measurement, a native release profile was detected because the medium was not stirred. In the case with stirring, however, method 2, 100% was released from those suppositories in the medium containing 1% polysorbate 80 with comparatively low standard deviations.These findings indicate that method 1 is most beneficial for a test comparing the effects of various factors such as additives and melting points on the release profiles of CO2 from the effervescent suppositories. However, this method is not practical for quality control of formulations because of the incomplete release of CO2; method 2, in contrast, is useful because of its complete release and low standard deviations.These results suggest that methods 1 and 2 for release tests of CO2 are most applicable to the early and late formulation studies of effervescent suppositories, respectively.View full abstractDownload PDF (693K) -
Toru HAKATA, Masao IIJIMA, Shigeo KIMURA, Hiroshi SATO, Yoshiteru WTAN ...1993 Volume 41 Issue 2 Pages 351-356
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFor the formulation of effervescent suppositories containing sodium bicarbonate and anhydrous sodium dihydrogen phosphate, the effects of bases and additives on the release profiles of carbon dioxide, CO2, from the suppositories were studied by an in vitro release test using a gas burette. The suppository bases employed were Witepsol[○!R] H-15, W-35 and E-85, and the additives were Aerosil[○!R] 200 and soybean lecithin. The melting points and viscosities of the suppositories were also measured to interpret the CO2 release profiles.The rate and amount of CO2 released from suppositories prepared with bases having different melting points and hydroxyl values decreased with increasing melting point and decreasing hydroxyl value. The addition of Aerosil[○!R] 200 to the suppository bases considerably reduced the rate and amount of CO2 released owing to the increasing viscosity of the melted bases, while the addition of soybean lecithin to those bases increased the rate and amount of CO2 released because of the improved wettability. Thus, the release profiles of CO2 from the effervescent suppositories were considerably influenced by the hydroxyl values related to the contents of mono- and di-glycerides, the melting points of the bases, Aerosil[○!R] 200 and soybean lecithin.This suggests that the rate and amount of CO2 released from the suppositories can be freely controlled by the combination of these various factors.View full abstractDownload PDF (756K) -
Hideki KAWAI, Yukisige KITANO, Masato MUTOH, Go HATA1993 Volume 41 Issue 2 Pages 357-361
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of dihydroxo(1R, 2R-cyclohexanediamine)platinum(II) with 2, 4-dioxopentanoic acid gave a water-soluble complex, (1R, 2R-cyclohexanediamine-N, N')[2-hydroxy-4-oxo-2-pentenoato(2-)-O2]platinum(II). The structure of the complex was determined by X-ray crystal analysis. The data indicated a chelation of the acetylacetonato part of 2, 4-dioxo-pentanoic acid to platinum(II). The complex showed moderate antitumor activity against murine leukemia L1210 in mice (T/C=195% at a dose of 200 mg/kg) and high activity against cisplatin-resistant L1210 leukemia (T/C=275% at a dose of 25 mg/kg).View full abstractDownload PDF (710K) -
Tomohisa NAGAMATSU, Hirofumi YAMASAKI, Takashi HIROTA, Masatoshi YAMAT ...1993 Volume 41 Issue 2 Pages 362-368
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS6-Phenyl analogs of toxoflavin {1-methyl-6-phenylpyrimido[5, 4-e]-1, 2, 4-triazine-5, 7(1H, 6H)-diones} (7a-f) and their 4-oxides (8a-f) were synthesized by nitrosative or nitrative cyclization of the aldehyde hydrazones (6a-f) of 6-(1-methylhydrazino)-3-phenyluracil (5). Both sets of compounds, 7a-f and 8a-f, gave the corresponding 1-demethyl derivatives (10a-f) upon treatment with nucleophiles such as dimethylformamide (DMF) and acetic acid under heating. The activities of toxoflavins (1a-e), toxoflavin 4-oxides (3a-e) and their 6-phenyl analogs (7a-f and 8a-f) against a variety of bacterial and fungal strains were examined. Most of the compounds showed strong inhibitory activities against gram-positive bacteria. Among the compounds, 1c, 1d, 1e, and 3c exhibited the strongest inhibitions of Micrococcus lutea (0.5 μg/ml minimal growth-inhibitory concentration) and Staphylococcus aureus 4R (1 μg/ml), as well as Bacillus subtilis and Staphylococcus aureus (1-2 μg/ml). Most of the compounds had strong antifungal activity (2-100 μg/ml minimal growth-inhibitory concentration) against Candida albicans and Saccharomyces cerevisiae.View full abstractDownload PDF (933K) -
Ryuji NAGATA, Yasuyuki ENDO, Koichi SHUDO1993 Volume 41 Issue 2 Pages 369-372
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWe aimed to synthesize ten-membered lactams ring-closed at C-4 of the indole by photocyclization reaction of γ-chlorotiglyl L-tryptophan methyl ester 5a for structure-activity study of medium-ring lactams related to indolactams having tumor-promoting activity. However, the 13C-NMR spectra of the products showed that two eight-membered lactams ring-closed at C-4 of the indole, (4S, 7S)-1, 3, 4, 5, 6, 7-hexahydro-4-methoxycarbonyl-7-methyl-6-oxo-7-vinylazocino[4, 5, 6-cd]indole (6a) and its (4S, 7R)-epimer 7a, and a seven-membered lactam ring-closed at C-2 of the indole, (2S, 5S)-1, 2, 3, 4, 5, 6-hexahydro-2-methoxycarbonyl-5-methyl-4-oxo-5-vinylazepino[4, 5-b]indole (8a), were produced rather than the expected ten-membered lactams 3a and 4a. That is, this photocyclization linked the carbon atom adjacent to the amide-carbonyl groups to the indole ring.View full abstractDownload PDF (622K) -
Tsutomu AGATSUMA, Akira TAKAHASHI, Chizuko KABUTO, Shigeo NOZOE1993 Volume 41 Issue 2 Pages 373-375
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA cytotoxic 14-membered resorcylic macrolide, isolated from Coriolus versicolor (L. : FR.) QUEL., was found to be identical with hypothemycin, previously isolated from Hypomyces trichothecoides TSUBAKI. The structure of hypothemycin has been elucidated to be 1 rather than the originally proposed 2.View full abstractDownload PDF (490K) -
Takeshi YAGAMI, Satoshi SHIWA, Shiroh FUTAKI, Kouki KITAGAWA1993 Volume 41 Issue 2 Pages 376-380
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAcidolytic deprotection and cleavage conditions for an acid-labile Tyr(SO3H)-containing peptide were systematically examined with respect to acid, temperature, and scavenger. The 90% aqueous trifluoroacetic acid (TFA)-based reagent systems (90% aqueous TFA/m-cresol and 90% aqueous TFA/m-cresol/2-methylindole) at 4°C were found to minimize the deterioration of Tyr(SO3Na) in the peptide. The latter deprotection/cleavage system was applied to the 9-fluorenylmethyloxycarbonyl (Fmoc)-based solid-phase synthesis of cholecystokinin (CCK)-12 on an acid-labile PAL-linked support (PAL=peptide amide linker), with Fmoc-Tyr(SO3Na)-OH as a building block.View full abstractDownload PDF (853K) -
Jun'ichi KOBAYASHI, Hideki SHINONAGA, Hideyuki SHIGEMORI, Takuma SASAK ...1993 Volume 41 Issue 2 Pages 381-382
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new C21 furanoterpene, untenospongin C (1), has been isolated from the Okinawan marine sponge Hippospongia sp. and its structure was determined on the basis of the spectroscopic data and chemical evidence. The absolute configuration of untenospongin B (2) was established by an examination of the NMR data for the 2-methoxy-2-trifluoromethylphenylacetic acid esters of 2.View full abstractDownload PDF (480K) -
Chihiro ITO, Tomohisa ONO, Keiichiro HATANO, Hiroshi FURUKAWA1993 Volume 41 Issue 2 Pages 383-385
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of glycocitrine-II (1), one of the acridone alkaloids having an ortho-prehylphenol moiety isolated from Citrus plants, with m-chloroperbenzoic acid (m-CPBA) in dichloromethane gave a novel oxidation product 2, along with the known cyclization products 3 and 4. The structure of 2 was elucidated by spectrometric and X-ray crystal-lographic analyses.View full abstractDownload PDF (574K) -
Michio KIMURA, Hajime KATAYAMA1993 Volume 41 Issue 2 Pages 386-387
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe molecular structure of the novel indole derivative, (2SR, 3aSR)-2-phenyl-2, 3, 3a, 4-tetrahydro-1H-pyrazolo[1, 5-a]indole which was obtained from 2-allylphenylhydrazone was established by X-ray diffraction methods.View full abstractDownload PDF (402K) -
Isamu MURAKOSHI, Toshikazu SEKINE, Kiyomi MAESHIMA, Fumio IKEGAMI, Koi ...1993 Volume 41 Issue 2 Pages 388-390
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn unusual amino acid, L-methionine sulfoximine (1), has been isolated from the fresh seeds of Cnestis palala (LOUR.) MERR. [Connaraceae]. The absolute configuration of the natural sulfoximine (1) was confirmed to be 2(S)-methionine S(S)-sulfoximine [(2S, SS)-2-amino-4-(S-methylsulfonimidoyl)-n-butanoic acid] by comparison of the [α]D value and IR spectrum with those of authentic samples obtained through the optical resolution of synthetic materials. Acute toxicity of the seeds of C. palala in a beagle dog was also studied.View full abstractDownload PDF (544K) -
Takayuki ASANO, Tetsuya MURAYAMA, Yasuaki HIRAI, Junzo SHOJI1993 Volume 41 Issue 2 Pages 391-393
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSix known homoisoflavonoidal compounds (1-6) and three new homoisoflavonoidal compounds (7-9) were isolated from the ether-soluble fraction of the subterranean part of Ophiopogon japonicus KER-GAWLER cv. Nanus. Among them, 1, 2, 3, 4, 5 and 6 were identified as methylophiopogonone A (1), ophiopogonone A (2), methylophiopogonanone A (3), ophiopogonanone A (4), JE-III (5) and desmethylisoophiopogonone B (6), respectively. The structures of compounds 7-9 were elucidated as 5, 7, 2'-trihydroxy-6-methyl-3-(3', 4'-methylenedioxybenzyl)chromone (7), 5, 7, 2'-trihydroxy-8-methyl-3-(3', 4'-methylenedioxybenzyl)chromone (8), and a racemate of 5-hydroxy-7, 8-dimethoxy-6-methyl-3-(3', 4'-dihydroxybenzyl)chroman-4-one (9), respectively.View full abstractDownload PDF (542K) -
Kazutaka WATANABE, Junei KINJO, Toshihiro NOHARA1993 Volume 41 Issue 2 Pages 394-396
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs part of our studies on leguminous plants, we examined the ingredients of Lupinus luteus L. and L. polyphyllus×arboreus hybrid, and three new isoflavonoid glycosides together with six known ones were isolated. They were determined to be 8-C-glucopyranosylgenistein 4'-O-glucopyranoside (1), 5-O-methylgenistein 4', 7-di-O-glucopyranoside (2), 2'-hydroxygenistein 4', 7-di-O-glucopyranoside (3) by spectroscopic and chemical methods. It was also shown that the isoflavonoid distributions in the two species were differed.View full abstractDownload PDF (496K) -
Hiroshi YUASA, Hiroyuki TAKAHASHI, Tetsuya OZEKI, Yoshio KANAYA, Masao ...1993 Volume 41 Issue 2 Pages 397-399
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to control the release rate of slightly water soluble medicine by using the solid dispersion (SD) method, the SD was prepared with a water soluble polymer and the slightly soluble medicine, and the medicine release from the solid dispersion granules was studied. The SD granules were prepared by the evaporation of ethanol after dissolving into ethanol a slightly water soluble medicine (flurbiprofen (FP)) and soluble polymers (hydroxypropyl cellulose (HPC)). HPC has four grades of molecular weight. The release rate of FP from SD was measured by the rotating basket method (JP XII).The release rate of FP from the SD granules was markedly larger than that from FP powder, and it was larger with a lower HPC molecular weight. It is speculated that these results were mainly based on the molecular dispersion state of FP and HPC in SD.View full abstractDownload PDF (467K) -
Sachiyo KUNIEDA, Toshiaki NISHIHATA, Hideo KASHIWAGI, Hiroshi TANIMURA1993 Volume 41 Issue 2 Pages 400-402
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA study to develop a sensitive method for measuring β-lactamase activity in bile was conducted. Since separation of substrate from biological components is required to increase the assay sensitivity and to achieve an accurate assay of β-lactamase activity, high performance liquid chromatography (HPLC) was used for separation and analysis of the substrates (cephaloridine for cephalosporinase, benzylpenicillin for penicillinase and cefuloxime for cefuloximase). In addition, conditions for increased assay sensitivity were also studied and optimal substrate concentrations and reaction times were determined. β-Lactamase activity of 0.05 munit/ml in bile was detected using the HPLC assay method which is a significant improvement when compared to the direct spectrophotometric method which has a detection limit of approximately 10 munit/ml.View full abstractDownload PDF (504K) -
Hideji ITOKAWA, Xu-Rong QIN, Hiroshi MORITA, Koichi TAKEYA, Yoichi IIT ...1993 Volume 41 Issue 2 Pages 403-405
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new 1, 2-seco-1-nor-6(5-10)-abeo-picrasan-2, 5-olide skeleton quassinoid named eurylactone and two new C19- and C20-skeleton quassinoids were isolated from the woods of Eurycoma longifolia (Simaroubaceae). Their structures were established by spectroscopic means.View full abstractDownload PDF (451K) -
Yuko TAKEMURA, Masami ABE, Motoharu JU-ICHI, Chihiro ITO, Keiichiro HA ...1993 Volume 41 Issue 2 Pages 406-407
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe chemical structure of acrignine-A (1), an acridone alkaloid carrying lignan moiety, from roots of Citrus plants (Rutaceae) have been elucidated by spectrometric studies using 1H-13C long-range COSY and NOE experiments. The structure was confirmed by single crystal X-ray analysis. This is the first example of an acridonolignoid isolated from natural sources.View full abstractDownload PDF (375K) -
Taisuke ITAYA, Takehiko IIDA, Hiromi EGUCHI1993 Volume 41 Issue 2 Pages 408-410
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOxalyl chloride reacts with a wide range of 1, 2-glycols in the presence of triethylamine to produce 1, 3-dioxolan-2-ones together with 1, 4-dioxane-2, 3-diones; the ratio of the products largely depends on the structure of the 1, 2-glycol. The formation of the cyclic carbonates may be rationalized in terms of stereoelectronically controlled cleavage of the tetrahedral intermediates.View full abstractDownload PDF (507K) -
Joseph MUNGARULIRE, Raphael M. MUNABU, Chikako MURASAKI, Tadashi EGUCH ...1993 Volume 41 Issue 2 Pages 411-413
Published: February 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structure and stereochemistry of a novel steroidal sapogenin, pogosterol (1), isolated from the leaves of Vernonia pogosperma has been established from spectral and single crystal X-ray analysis.View full abstractDownload PDF (404K)
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