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Volume 41, Issue 5
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Hideko KAWAKI1993 Volume 41 Issue 5 Pages 797-803
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThermodynamic parameters were determined by variable temperature experiments on the gas-liquid chromatography (GLC) relative retention values, log γ, of mono-substituted benzene derivatives. The free energy change ΔΔG°s which is estimated from the enthalpy ΔΔH°s and the entropy ΔΔS°s at 298 K is less than -15kJ·mol-1, corresponding to an interaction between the sample and the liquid stationary phase. With regards to the co-linearlity with the standard entropy S°(B··C) of the complex, between the sample and the liquid stationary phase, an excellent linear relationship of ΔΔS°s with the electron-donating and -withdrawing groups was obtained. The log γ can also be expressed by the linear combination of the descriptors σs°, μ2/α, and σR which are the dispersion and repulsion, the induction and orientation, and the charge transfer interaction energies respectively, and from the evaluation of the standard coefficient by the z-score of log γ, (Edis+Erep)>ECT>(Eind+Eori). Under non-polar conditions, (Edis+Erep) was dominant while under polar conditions, the ratio of [(Eind+Eori)+ECT] increased to the level of (Edis+Erep).View full abstractDownload PDF (868K) -
Toshimasa ISHIDA, Yasuko IN, Yuki HIRASE, Kouji SHIHODA, Masatoshi INO ...1993 Volume 41 Issue 5 Pages 804-809
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe solution conformation of 5'-O-[N-(L-alanyl)sulfamoyl]adenosine (ala-SA), an analogue of alanyl-AMP, was studied by 1H-NMR spectroscopic and energy calculation methods for elucidating the substrate-specificity of the cognate alanyl-tRNA synthetase. The ala-SA molecule existed in several conformational equilibria such as anti⇌syn, C3'-endo⇌C2'-endo and gauche·gauche⇌gauche·trans (or trans·gauche) orientations concerning the glycosyl bond, ribose puckering and exocyclic C4'-C5' bond, respectively. However, their populations were solvent-dependent, and the major form in D2O solution could be characterized as the anti-C2'-endo-gauche·gauche conformation, although no predominant conformation, except for C2'-endo ribose puckering, existed in dimethyl sulfoxide solution. Possible conformers satisfying the NMR data were surveyed using empirical energy calculations, and the solution conformation of the ala-SA molecule was compared with its crystal conformation.View full abstractDownload PDF (780K) -
Taiko ODA, Mitsuru WATANUKI, Yoshihiro SATO, Tadashi HATA1993 Volume 41 Issue 5 Pages 810-815
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDietylstilbestrol oxide is a metabolic intermediate of diethylstilbestrol. In order to elucidate the effects of optically active diethylstilbestrol oxides on microtubule assembly and cell culture, we synthesized (±)-diethylstilbestrol oxide(2a). Since 2a was not stable under moderately acidic and basic conditions, the monomethyl ether (2c) of diethylstilbestrol oxide, which was more stable than 2a, was separated by high-pressure liquid chromatography using a chiral column.The mono (4-bromobenzoate) of (-)-2c was analyzed by X-ray crystallography and its absolute structure was determined as C (1R, 1'R).View full abstractDownload PDF (958K) -
Hajime KATAYAMA, Noriyuki TAKATSU, Yohko TAKEUCHI, Michiyo YAMAGIWA1993 Volume 41 Issue 5 Pages 816-821
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFischer indolization of the hydrazones of 8-allyl-1-amino-, 1, 2, 3, 4-tetrahydroquinoline and related compounds was investigated. Fischer indolization induced Cope rearrangement of the allyl group and acid-catalyzed intramolecular cycloaddition between the hydrazonyl group and the vinyl group. The base treatment of the latter reaction product caused eliminative ring-opening of the adduct and led to the formation of an indoline skeleton bearing a 2-ketoalkyl group at the C-2 position.View full abstractDownload PDF (1121K) -
Kiyoshi NISHITANI, Yukitaka NAKAMURA, Ryouki ORII, Chiko ARAI, Koji YA ...1993 Volume 41 Issue 5 Pages 822-831
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSα-Methylene-γ-lactones fuses to five- and six-membered carbocycles were efficiently synthesized from β-ethoxycarbonyl-ω-formylallylsilane derivatives by means of the intramolecular Hosomi reaction. The formylated allylsilanes (11a, b, 12a and b) were synthesized from ethyl β-trimethylsilylpropionate and ω-tetrahydropyranyloxy-pentanal (4a) and -hexanal (4b) in several steps. The cyclization reaction of these aldehydes was performed under mild conditions with a high degree of stereocontrol. Treatment of the (E)- and (Z)-isomers of the allysilanes (11a and 12a) with titanium tetrachloride or boron trifluoride etherate gave a five-membered cis-hydroxy ester (13a). Treatment of the (Z)-allylsilane derivative (11b) with titanium tetrachloride afforded a six-membered cis-hydroxy ester (13b) as a major product together with the trans-isomer (14b), and treatment with boron trifluoride etherate selectively gave the cis-isomer (13b). On the other hand, treatment of (E)-allylsilane (12b) with titanium tetrachloride selectively gave the cis-hydroxy ester (13b), while the use of boron trifluoride etherate exclusively afforded the trans-isomer (14b).These stereoselectivities can be explained in terms of chelated transition models. Lactonization of these hydroxy esters afforded the corresponding fused α-methylene-γ-lactones (16a, 17a and b) in good yields.View full abstractDownload PDF (1565K) -
Jian Xin LI, Shigetoshi KADOTA, Masao HATTORI, Sadao YOSHIMACHI, Motoo ...1993 Volume 41 Issue 5 Pages 832-841
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTen new highly oxidized cycloartane-type triterpenoids, 24-epi-7, 8-didehydrocimigenol, 7, 8-didehydrocimigenol, 25-O-acetyl-7, 8-didehydrocimigenol, 3-keto-24-epi-7, 8-didehydrocimigenol, 2', 4'-O-diacetyl-24-epi-7, 8-didehydrocimigenol-3-xyloside, 3'-O-acetyl-24-epi-7, 8-didehydrocimigenol-3-xyloside, 24-epi-7, 8-didehydrocimigenol-3-xyloside, 7, 8-didehydro-24-O-acetylhydroshengmanol-3-xyloside, 24-epi-acerinol and heracleifolinol, were isolated from the rhizome of Cimicifuga heracleifolia KOMAROV and their structures were determined by the use of two-dimensional nuclear magnetic resonance (2D NMR) techniques (1H-1H correlation spectroscopy (COSY), 1H-13C COSY, 1H-13C long-range COSY) and by X-ray diffraction analysis of the 3-keto compound.View full abstractDownload PDF (1287K) -
Hiroshi SHIMIZU, Tadashi KATAOKA, Mikio HORI1993 Volume 41 Issue 5 Pages 842-845
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of 9-phenylthioxanthene 10-oxide (1) with a variety of Grignard reagents afforded 9-substituted 9-phenylthioxanthenes (2). Similarly, organolithiums reacted with the sulfoxide 1 to give the corresponding thioxanthenes 2. The structures of 9-aryl-9-phenylthioxanthenes (2d-i) were confirmed by the alternative synthesis of the samples via the acid-catalyzed cyclization of triarylmethanol derivatives 5. A possible mechanism by way of a 9-phenylthioxanthylium ion intermediate is proposed for the reaction of the sulfoxide 1 with organometallic reagents.View full abstractDownload PDF (567K) -
Takehiro SANO, Hiroshi ENOMOTO, Kenji YASUI, Yoshie HORIGUCHI, Fumiyuk ...1993 Volume 41 Issue 5 Pages 846-853
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe photocycloaddition reactions of 4, 5-diethoxycarbonyl-1H-pyrrole-2, 3-dione (6) to cycloalkadienes and cycloalkenes were examined. The addition of cyclopentadiene gave the hydroindole 8a (s+a product) as a major product and the cis-fused cyclobutane 7a (s+s product) as a minor one. In contrast, the addition of cyclohexadiene gave the cyclobutane 7b (s+s product) as a major product and the hydroidole 8b (s+a product) as a minor one. The photocycloaddition of cyclopentene, cyclohexene, and indene proceeded predominantly in an s+s manner to give the cis-syn-cis cyclobutanes, 16, 18, and 19, respectively. The stereochemical results were compared with those of the photocycloaddition reaction of 4-ethoxycarbonyl-5-phenyl-1H-pyrrole-2, 3-dione (1) to the corresponding cyclo-olefins, revealing that the steric relationship of the addends plays an important role in determining the stereochemical pathway of the reaction.View full abstractDownload PDF (1159K) -
Iwao UTSUNOMIYA, Masahiro FUJI, Tomohiro SATO, Mitsutaka NATSUME1993 Volume 41 Issue 5 Pages 854-860
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEffective pathways for an enantiospecific synthesis of (1aS, 8bS)-1-tert-butyloxycarbonyl-8-formyl-1, 1a, 2, 8b-tetrahydroazirino[2', 3' : 3, 4]pyrrolo[1, 2-α]indole (8) were investigated as a preliminary experiment aiming at chiral syntheses of aziridinomitosenes 5 and (1aS, 8bS)-8-[[(aminocarbonyl)oxy]methyl]-5-formyl-7-hydroxy-1, 1a, 2, 8b-tetra-hydroazirino[2', 3' : 3, 4]pyrrolo[1, 2-α]indone (6a). An aldehyde 14, derived from L-serine was condensed with 2-lithio-1-(phenylsulfonyl)indole (10) to afford diastereomers 15a and 15b, whose stereochemistry was unambiguously determined by 1H-NMR studies of the 1, 3-dioxane derivatives 17a, 17b, and 18 as well as the X-ray crystallographic analysis of a dihydropyrrolo[1, 2-α]indole derivative 31a. The latter compound was prepared from 15a via the following operations(Chart 5) : (i) removal of the acetonide and the indole-protecting groups, followed by acetylation to form 29a, (ii) Vilsmeier reaction to produce 30a, and (iii) hydrolysis of acetyl groups, partial methanesulfonylation (mesylation), and treatment with potassium carbonate in acetonitrile. A diastereomer 31b was obtained from 15b in a similar manner.Both isomers 31a and 31b afforded the desired compound 8 upon treatment with a mesylation reagest followed by potassium tert-butoxide in tetrahydrofuran.View full abstractDownload PDF (1363K) -
Koji OKANO, Takashi EBATA, Koshi KOSEKI, Hiroshi KAWAKAMI, Katsuya MAT ...1993 Volume 41 Issue 5 Pages 861-865
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS(+)-Grandisol, which is a component of the male-produced pheromone of the boll weevil, Anthonomus grandis, was synthesized from levoglucosenone. The key steps in the synthesis are the intramolecular diatereoselective four-membered ring construction and the Baeyer-Villiger oxidation. The 17-step procedure led to a known synthetic intermediate of (+)-grandisol.View full abstractDownload PDF (848K) -
Toshiko TANIMOTO, Tomoko SAKAKI, Kyoko KOIZUMI1993 Volume 41 Issue 5 Pages 866-869
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour regioisomeric ditritylated derivatives of cyclomalto-octaose (1, cG8), namely, 61, 6n-di-O-trityl-cG8s have been prepared by the reaction of 1 with chlorotriphenylmethane in pyridine and isolated by high-performance liquid chromatography. The regiochemical determination of the four ditrityl-substituted derivatives has been achieved by means of the "hex-5-enose degradation, " followed by examination of the products by fast-atom bombardment-mass spectrometry.View full abstractDownload PDF (594K) -
Shigehiro TAKEGAWA, Naoyuki KOIZUMI, Hiroo TAKAHASHI, Kenyu SHIBATA1993 Volume 41 Issue 5 Pages 870-875
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOxygenated derivatives of 2-oxachlormadinone acetane (17-acetoxy-6-chloro-2-oxapregna-4, 6-diene-3, 20-dione) at C11, C15, and C16 were prepared as potential antiandrogenic agents. Biological evaluation showed the 15β-hydroxyl compound to have a high potent antiandrogenic activity when tested in the castrated male rat.View full abstractDownload PDF (926K) -
Koji YONEDA, Atsutoshi OTA, Yoichi KAWASHIMA1993 Volume 41 Issue 5 Pages 876-881
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of N-(mercaptoalkyl)thiazolidine-2-thiones and their derivatives were synthesized and evaluated for hepatoprotective activities against Propionibacterium acnes-lipopolysaccharide (P. acnes-LPS)-induced liver injury in mice and in vitro lipid peroxide (LPO) formation in rat liver microsomes. Reaction of N-(p-methoxybenzylthioalkyl)cysteine methyl ester (11) with 1, 1'-thiocarbonyldiimidazole followed by deprotection gave the corresponding thiazolidene-2-thione derivatives. Among the compounds synthesized, 1a and 2a showed the most potent hepato-protective activities against P. acnes-LPS-induced liver injury. Compounds 1a-f and 4 inhibited LPO formation in vitro. Compounds 1a and 2a were chosen for further pharmacological evaluations.View full abstractDownload PDF (1029K) -
Mitsuo SUGIYAMA, Toshiaki SAKAMOTO, Yumiko KAMIGAKI, Hiroshi FUKUMI, K ...1993 Volume 41 Issue 5 Pages 882-888
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new series of piperidineacrylate derivatives was prepared and evaluated for antiallergic activity. Most of the compounds showed potent activities in the rat passive cutaneous anaphylaxis (PCA) assay. In particular, ethyl 1-[2-bis(4-fluorophenyl)methoxyethyl]-4-piperidimeacrylate (1a) was more potent than oxatomide and terfenadine in this assay, and was selected for further study. Some pharmacological properties of 1a are presented.View full abstractDownload PDF (1097K) -
Tsuneaki HIDA, Shigetoshi TSUBOTANI, Akira HORI, Morio MURAKAMI, Hidea ...1993 Volume 41 Issue 5 Pages 889-893
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSperabillin A, 3-[[(3R, 5R)-3-amino-6-[(2E, 4Z)-2, 4-hexadienoylamino]-5-hydroxyhexanoyl]amino]propanamidine dihydrochloride, was polymerized on standing for several days under a highly humid atmosphere or in the presence of radical initiators. The average molecular weight of the polymers obtained could be regulated by changing the reaction conditions in the latter case. Spectral analyses of the polymers revealed that the 2, 4-hexadienoyl moiety of sperabillins was polymerized in a free radical-initiated reaction. The polymers selectively inhibited the proliferation of human umbilical vein endothelial (HUVE) cells. Polymers having higher molecular weight showed stronger inhibition of HUVE cell proliferation. In addition, the polymers showed anti-tumor activity against B16 melanoma in vivo.View full abstractDownload PDF (743K) -
Katsuya NAKAMURA, Kiyoshi TSUJI, Nobukiyo KONISHI, Hiroyuki OKUMURA, M ...1993 Volume 41 Issue 5 Pages 894-906
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structure of previously reported new antiinflammatory agent (1, FK3311) was chemically modified in an attempt to find novel compounds with more potent and broader-spectrum activities. Some 2'-(phenylthio) and 2'-(phenylamino)methanesulfonanilides (2 and 3), in particular those bearing an electron-attracting substituent at the 4'-position, potently inhibited adjuvant arthritis in rats as well as collagen-induced arthritis in mice when administered orally. 4'-Carbamoyl-2'-(2, 4-difluorophenylthio)methanesulfonanilide (3b), which was selected as a candidate for further development from among the compounds synthesized herein, exhibited activity in reducing arthritis in a spontaneous autoimmune disease model (MRL/lpr mice) within the dose range of 10-100 mg/kg (p.o).View full abstractDownload PDF (1604K) -
Tadafumi TERADA, Katsuhiko FUJIMOTO, Makoto NOMURA, Jun-ichi YAMASHITA ...1993 Volume 41 Issue 5 Pages 907-912
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1-β-Alkyl derivatives of 1-desoxypodophyllotoxin were synthesized, and their cytotoxicity and inhibitory effects on DNA topoisomerase II (Topo-II) and tubulin polymerization were examined.The reaction of epipodophyllotoxin derivatives (1a-c) with trimethylallylsilane in the presence of boron trifluoride etherate gave 1-β-allylated compounds (2a-c). The regiochemistry and the β-stereochemistry of the 1-allyl group were confirmed by comparison of the 13C-NMR spectra and NOE's (%) of 2c, podophyllotoxin (POD) and epipodophyllotoxin (1b). 1-β-Alkyl-1-desoxypodophyllotoxin derivatives (3-8) were prepared from 2b.None of the tested compounds (3-8) showed any inhibitory effect on Topo-II. 1-β-Propyl compound (3) and its 4'-demethyl compound (4) inhibited tubulin polymerization and the cytotoxicities of these compounds were equal to that of VP-16. 1-β-(2, 3-Dihydroxypropyl) compounds (5 and 8) and 1-β-(2, 3-diacetoxypropyl) compounds (6 and 7)showed no inhibitory effect on tubulin polymerization. Although 5 did not inhibit either Topo-II activity or tubulin polymerization, it showed a high cytotoxicity against sarcoma 180.View full abstractDownload PDF (896K) -
Koichi KOJIMA, Shigeo AMEMIYA1993 Volume 41 Issue 5 Pages 913-918
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS3-Oxa-5-methyleneisocarbacyclin (14a) and 3-Oxa-5-ethylideneisocarbacyclin (19a) were synthesized. Compound 14a showed a potent antiplatelet aggregating activity, whereas 19a was inactive.View full abstractDownload PDF (993K) -
Jun KOBAYASHI, Motoichi MIYAZAKI1993 Volume 41 Issue 5 Pages 919-922
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSChelating glass beads (SAB) containing salicylideneamino-2-thiophenol (SATP) as a functional group were synthesized for the selective adsorption and separation of ionic aluminum (Al3+). SAB was prepared by reacting amino-propyl-CPG (controlled pore glass) with SATP, shielded from light in toluene at 110°C for 12 h. The exchange capacity of SAB for Al3+ was about 1.1 mmol/g (support). When SAB was packed into a column, only Al3+ was retained out of all the metal ions examined, at pH 5.5 with hydroxylamine hydrochloride present. Aluminum ion was then eluted quantitatively with nitric acid. Aluminum samples below 1 ppm were concentrated by a factor of 100. This column method applied to the preconcentration of Al3+ in drinking water.View full abstractDownload PDF (644K) -
Naoki TAKEUCHI, Takashi FUJITA, Kaori GOTO, Naomi MORISAKI, Naoko OSON ...1993 Volume 41 Issue 5 Pages 923-925
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new trinor-guaiane type sesquiterpene, named dictamnol (1), and a steroid, pregnenolone (2), were isolated from Dictamnus dasycarpus TURCZ. On the basis of physicochemical evidence, the structure of dictamnol have been elucidated as 8α-methyl-2-methylene-1α, 7α-dicyclo[3.5.0]dex-5-en-8β-ol.View full abstractDownload PDF (539K) -
Emi OKUYAMA, Satoshi NISHIMURA, Shigeru OHMORI, Yukihiro OZAKI, Motoyo ...1993 Volume 41 Issue 5 Pages 926-929
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNotopterol was identified as the analgesic component of Notopterygium incisum TING by using the acetic acid-induced writhing method. Notopterol also indicated an anti-inflammatory activity by its inhibitory effect in the vascular permeability test. The intensive prolongation of pentobarbital-induced hypnosis was possibly caused by its inhibitory effect on the drug metabolism in liver. Pharmacological differences between the analgesic components of N. incisum, Aralia cordata and Angelica pubescens were also discussed.View full abstractDownload PDF (644K) -
Yumi KUROKAWA-NOSE, Tsumoru SHIMADA, Hiroshi WADA, Nobutoshi TANAKA, T ...1993 Volume 41 Issue 5 Pages 930-932
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA novel 2-tetralol-type xyloside, named asplenoside, was isolated from the fronds of Asplenium wilfordii. The structure was determined as (6R)-5, 6, 7, 8-tetrahydro-6-β-D-xylopyranosyloxy-2-naphthalenecarboxylic acid by chemical and spectral means. Application of the glycosylation shift rule in 13C-NMR spectroscopy to the determination of the absolute configuration is described.View full abstractDownload PDF (641K) -
Hiroshi YUASA, Tetsuya OZEKI, Yoshio KANAYA, Katsutoshi OISHI1993 Volume 41 Issue 5 Pages 933-936
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSolid dispersions were prepared by the evaporation of ethanol after dissolving into ethanol a water soluble medicine(oxprenolol hydrochloride (OXP)), four grades of water insoluble ethylcellulose (EC) and four grades of water soluble hydroxypropyl cellulose (HPC), both having different molecular weights. The precise control of the release rate of a water soluble medicine by applying the difference in the molecular weight of polymers was attempted. The pore size distribution in solid dispersion granules was measured before and after the dissolution test by mercury intrusion porosimetry to clarify the mechanism of medicine release from the granules when the molecular weights of polymers were different. The state of medicine in the solid dispersions was analyzed by thermal analysis and X-ray diffractometry.Although the difference was slight, the release rate of OXP from the granules of the OXP-HPC system decreased as the molecular weight of HPC increased. The release behavior of OXP in the OXP-EC system was scarcely affected by the molecular weight of EC. However, in the OXP-EC-HPC system, the release rate markedly decreased with a larger molecular weight of EC. It was thought from the results of the pore size distribution that there were two types of release routes for OXP; dissolving directly into the dissolution medium, and diffusing in the swelled HPC phase, caused by the addition of HPC. The decrease in the release rate of OXP in the OXP-EC-HPC system was caused by the increase in the ratio of OXP dissolving via the latter route, occurring with a larger molecular weight of EC.These results suggest that it is feasible to precisely control the release of a water soluble medicine by varying the molecular weight of the polymers in the solid dispersion.View full abstractDownload PDF (641K) -
Noritaka SEKO, Hisakazu SUNADA, Kazumi DANJO, Akinobu OTSUKA, Yorinobu ...1993 Volume 41 Issue 5 Pages 937-941
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe granulation from mixed crude drug powders was carried out by fluidized bed and agitation methods. The effects of the physical properties of the binder solution, such as the contact angle on the powder compact, the viscosity, on the granule characteristics, the average granule size, angle of repose, bulk density, granule strength, compressibility, and strength of compact, were examined.Correlation between the physical properties of the products obtained by fluidized bed granulation and agitation granulation, and those of the binder solution were analysed by using the correlation formula derived from multiple regression analysis. A highly confident multiple correlation was found and the relationship between physical properties of the binder solution and those of the granules can be expressed quantitatively.It suggests the possibility that formulation of powder materials for production of granules having desirable physical properties can be easily determined and, also, the granulating manipulation which has been performed experimentally or qualitatively, can be done quantitatively and rationally, by using the results.View full abstractDownload PDF (655K) -
Masahiko SUZUKI, Kiyoko ITO, Chigusa FUSHIMI, Tamotsu KONDO1993 Volume 41 Issue 5 Pages 942-945
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe interaction and the self-association of a variety of compounds in aqueous solution were investigated by the freezing point depression method using a commercially available osmometer. This method, described in our earlier publication, was used to determine the stability constant and self-association constant, which were based on the colligative properties of solution and calculated from the decrease of osmotic pressure obtained in terms of the freezing point depression. Stability constants were measured for complexes of α-, β-, and γ-cyclodextrin with non-aromatic carbonic acids (acetic acid, formic acid, oxalic acid, succinic acid, malic acid, tartaric acid, maleic acid, citric acid), anions (I-, NO-3, ClO-4, CNO-, SCN-, Cr2O2-7) and amino acids (leucine, isoleucine, methionine, phenylalanine, tryptophan), and the self-association constant for caffeine was measured. These values gave good reproducibility and rapid estimation with a simple procedure. It was concluded that the freezing point depression method is useful for estimation of the stability constant and the self-association constant for drugs in aqueous solution.View full abstractDownload PDF (585K) -
Chuzo IWATA, Naoyoshi MAEZAKI, Kohji HATTORI, Masahiro FUJITA, Yasunor ...1993 Volume 41 Issue 5 Pages 946-950
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe total synthesis of (+)-talaromycin A and (-)-talaromycin B was accomplished by utilizing a common intermediate (3). The spiroketal (3) was converted to the olefin (4) via thermolysis of the sulfinyl group, C1-unit elongation at the C9-position, and isomerization at the spiro center. On the other hand, 3 was isomerized to 7 at the C9-position and then converted to the olefin (5) in a similar manner to that described for (+)-talaromycin A. These intermediates (4 and 5) were transformed into (+)-talaromycin A and (-)-talaromycin B via addition reaction of trifluoroacetic acid and oxymercuration, respectively.View full abstractDownload PDF (782K) -
Zahid Hussain CHOHAN, Samina KAUSAR1993 Volume 41 Issue 5 Pages 951-953
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNew tridentate pyrimidine-derived NNO and NNS donor Schiff base ligands and their nickel(II), copper(II) and zinc(II) chelates have been synthesized and characterized on the basis of elemental analysis, 1H-NMR, IR and electronic spectral data and conductance and magnetic measurements. The synthesized ligands and their metal chelates have been screened and compared for their antibacterial action against bacterial species Escherichia coli, Pseudomonas aeruginosa and Klebsiella pneumoniae.View full abstractDownload PDF (544K) -
Hirokazu TAMAMURA, Junko NAKAMURA, Katsuhiro NOGUCHI, Susumu FUNAKOSHI ...1993 Volume 41 Issue 5 Pages 954-957
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn solid-phase peptide synthesis, the addition of m-cresol to dilluted methanesulfonic acid (MSA) in dichloromethane accelerated the deprotection rate of the acid-labine α-amino protecting group, the p-methoxybenzyloxycarbonyl(Z(OMe)) group. Further, 0.1 M MSA, 20% m-cresol/CH2Cl2 was found to be a practically useful Nα-deprotecting reagent system, since the deprotection of the Z(OMe) group occurred selectively within 30 min at room temperature, leaving intact the other side chain protecting groups, such as benzyloxycarbonyl, benzyl ester, S-p-methoxybenzyl and NG-mesitylene-2-sulfonyl groups. This reagent system was applied to the Z(OMe)-based solid phase syntheses of human pancreastatin-29 and magainin 1.View full abstractDownload PDF (724K) -
Shin-ichiro SAKAI, Makiko KATSURA, Hiromitsu TAKAYAMA, Norio AIMI, Nan ...1993 Volume 41 Issue 5 Pages 958-960
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs part of a survey of anti-tumorpromotive chemicals, garcinone E (1) and nine known xanthones, 8-deoxygartanin, gartanin, xanthone I, β-mangostin, garcinone B, 6-deoxy-γ-mangostin, 1, 5, 8-trihydroxy-3-methoxy-2-(3-methyl-2-butenyl)xanthone, γ-mangostin and α-mangostin, together with egonol, were isolated from the fruit hulls of Garcinia mangostana L. collected in Thailand. The structure of garcinone E was elucidated as 1, 3, 6, 7-tetrahydroxy-2, 5, 8-tri-(3-methyl-2-buteny)xanthone by spectroscopic methods, including the application of a number of two dimensional (2D)NMR techniques (1H-1H, 13C-1H correlation spectroscopy (COSY), nuclear Overhauser effect spectroscopy (NOESY) and correlation via long-range coupling (COLOC).View full abstractDownload PDF (561K) -
Toshio SHIDA, Hisaya IWAORI, Masahiko ARAKAWA, Junichi SEKIGUCHI1993 Volume 41 Issue 5 Pages 961-964
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTo elucidate the conformational properties of DNA with a 2-deoxyribosylformamide residue (dF), an oligodeoxyribonucleotide containing this abasic residue in a specific position of the nucleotide sequence was synthesized by the standard solid-phase phosphotriester method. Deprotection of the synthesized oligonucleotide was performed under routine alkaline and acidic conditions. The presence of a dF residue in the oligomer was confirmed by ion-spray mass spectrometry. A dF residue was found to affect considerably the stability of the DNA duplex, as determined from the melting behavior of the dF-containing duplex.View full abstractDownload PDF (641K) -
Yoshisuke TSUDA, Shinzo HOSOI, Fumiyuki KIUCHI, Jun TODA, Ryuzo YAMAMO ...1993 Volume 41 Issue 5 Pages 965-967
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2, 3-Dichloro-5, 6-dicyano-1, 4-benzoquinone (DDQ) oxidation of 3, 8-dioxyoerythrinan-1(6)-enes in dioxane gave the ring B dehydrogenated products, the 1, 6-dienones, while oxidation in benzene gave the fully dehydrogenated products, the 1, 6, 10-trienones. The same trienones were obtained by DDQ oxidation of the 1, 6-dienones in bezene. On the contrary, oxidation of the isomeric enone, 3, 8-dioxoerythrinan-1-ene, in either dioxane or benzene gave the ring C dehydrogenated product, the 1, 10-dienone. The 1, 6, 10-trienones were transformed to the highly dehydrogenated 8-oxoerythrinan alkaloids, erytharbine and crystamidine, in racemic forms.View full abstractDownload PDF (562K) -
Mitsuaki WATANABE, Hitoshi MORIMOTO, Kayoko NOGAMI, Saori IJICHI, Suna ...1993 Volume 41 Issue 5 Pages 968-970
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA regioselective annulation to naphthalene ring systems from dimethyl phthalide-3-phosphonates and electron-deficient olefins is described.View full abstractDownload PDF (498K) -
Takashi YAEGASHI, Seigo SAWADA, Tomio FURUTA, Teruo YOKOKURA, Kentaro ...1993 Volume 41 Issue 5 Pages 971-974
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structure of the N-amino pyridone (4a) obtained by the reaction of camptothecin (1a) with hydrazine was determined by X-ray crystallography. A mixture of 7-etylcamptothecin (1b) and hydrazine hydrate was stirred at room temperature, and the hydrazide (2b) was isolated as its diacetate 2c. Treatment of the 17-O-acetyl amide (5a) with hydrazine gave 1b (74% yield) and the N-amino lactam 6 (11% yield). Compounds with bulky acyl groups, 5c-e, gave 6 in modest yields. The N-amino lactam 6 was smoothly dehydrated into the pyridone 4d by refluxing in hydrazine hydrate.View full abstractDownload PDF (606K) -
Koichi KAWASAKI, Masanori MIYANO, Katsuhiko HIRASE, Masahiro IWAMOTO1993 Volume 41 Issue 5 Pages 975-977
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPeptide analogs of the N-terminal portion of fibrin α-chain were prepared and their inhibitory effects on fibrinogen/thrombin clotting were examined. Of the synthetic peptides, H-Gly-Pro-Arg-Pro-Pro-NH2 exhibited the most potent inhibitory effect.View full abstractDownload PDF (630K) -
Hirokazu TAMAMURA, Rie IKOMA, Makoto NIWA, Susumu FUNAKOSHI, Tsukasa M ...1993 Volume 41 Issue 5 Pages 978-980
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWe investigated the structure-antimicrobial activity relationship of tachyplesin I (T-I). Even when Lys1 and Trp2 were both deleted from the N-terminal end of T-I, the antimicrobial activity against gram-negative bacteria was not decreased. But as Lys1 and Trp2 were deleted one by one, the antimicrobial activity against gram-positive bacteria and antiviral activity were gradually decreased. Deletion of two disulfide bridges caused a significant decrease in all activities. The circular dichroism (CD) spectra revealed that the analogs containing the two disulfide bidges took a β-sheet structure and that the analogs without the disulfide bridges took a random coil conformation. These results suggest that the β-sheet structure maintained by two disulfide bridges plays an important role in the antimicrobial activity of T-I.View full abstractDownload PDF (576K) -
Shigeru KUROSAWA, Daiju MATSUI, Naoki KAMO1993 Volume 41 Issue 5 Pages 981-982
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS4, 4'-Methylenedianiline was plasma-polymerized on a platinum plate; the monomer was sublimated, followed by discharging for polymerization. The emf between the platinum plate covered with the plasma-polymerized film and Ag/AgCl electrode was measured, and it was found that a nearly Nernstian response to pH (slope of -60 mV pH-1)was given over the range 4 to 10. The film was characterized with scanning electron microscope and Fourier-transform infrared spectroscopy.View full abstractDownload PDF (452K) -
Sompol PRAKONGPAN, Wiriya LIMCHALERM, Tsuneji NAGAI1993 Volume 41 Issue 5 Pages 983-985
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFerrous compound was used as a free oxygen absorber (FOA). It was prepared from the chemical reaction of ferrous sulfate and sodium hydroxide under nitrogen atmosphere. The condition of reaction was investigated to obtain a product of high absorbing activity. A kinetic study was done when FOA was exposed to the air and the efficacy was tested.View full abstractDownload PDF (517K) -
Eiji HIMENO, Tsuneatsu NAGAO, Junko HONDA, Hikaru OKABE, Nobuto IRINO, ...1993 Volume 41 Issue 5 Pages 986-988
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSix glucosides of novel 29-nor-cucurbitacins having non-aromatized A ring were isolated from the roots of Cayaponia-tayuya. Elucidation of their structures by spectral analyses is described.View full abstractDownload PDF (415K) -
Motomasa KOBAYASHI, Shunji AOKI, Haruhiko SAKAI, Noriaki KIHARA, Takum ...1993 Volume 41 Issue 5 Pages 989-991
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFollowing the characterization of altohyrtin A (1), altohyrtins B (2) and C (3) and 5-desacetylaltohyrtin A (4) have been isolated from the Okinawan marine sponge Hyrtios altum and their plane structures and parts of their relative configurations elucidated. Three congeneric macrolides (2, 3, and 4) exhibit extremely potent cytotoxicities similar to those of 1 against KB cells with IC50 values of 0.02, 0.4 and 0.3 ng/ml, respectively.View full abstractDownload PDF (452K) -
Hiroshi MORITA, Shinji NAGASHIMA, Koichi TAKEYA, Hideji ITOKAWA1993 Volume 41 Issue 5 Pages 992-993
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo novel antitumor chlorine- and allo Thr-containing cyclic pentapeptides, named astins A and B, both of which were isomers and took a cis configuration in one of the amide bonds, were isolated from Aster tataricus together with astin C. Their structures were solved by spectroscopic analysis and chemical degradation.View full abstractDownload PDF (387K) -
Kazumasa AOKI, Makoto NAKAJIMA, Kiyoshi TOMIOKA, Kenji KOGA1993 Volume 41 Issue 5 Pages 994-996
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMaximum rotations of (R)-4-tert-butyl-, (R)-4-phenyl- (R)-4-isopropyl, and (R)-4-methyl-1-trimethylsilyloxycyclohexenes ((R)-3a, (R)-3b, (R)-3c, and (R)-3d) were determined to be[α]36525 +237° (benzene), [α]36525 +146° (benzene), [α]36525 +228° (benzene), and [α]36525 +238° (benzene), respectively.View full abstractDownload PDF (408K) -
Isao KITAGAWA, Kazuyuki MINAGAWA, Ru-song ZHANG, Kazuyuki HORI, Mitsun ...1993 Volume 41 Issue 5 Pages 997-999
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThrough bioassay-guided separations of the chemical constituents of the Indonesian medicinal plant Beilschmiedia madang BL. a bisbenzylisoquinoline alkaloid was obtained as the major antimalarial principle. The physicochemical properties of the alkaloid were consistent with the proposed structure of dehatrine (1). However, the alkaloid isolated by us was shown to be a mixture of two rotational isomers. The X-ray crystallographic analysis of 1 has shown that two rotamers are incorporated in a single crystal in 1 : 1 ratio. The complex NMR spectrum of 1 has also been defined as a mixture of two rotamers by extensive use of 2D (COSY and COLOC) techniques. Dehatrine (1) has been shown to significantly inhibit the growth of cultured Plasmodium falciparum K1 strain (cholorquine resistant) with similar activity to quinine.View full abstractDownload PDF (489K) -
Kitaro OKA, Toshihiko HIRANO, Masato HOMMA, Hiromitsu ISHII, Kiyotaka ...1993 Volume 41 Issue 5 Pages 1000-1002
Published: May 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWe optimized HPLC conditions for the first time to achieve satisfactory separation of six surfactins, two of which were novel, isolated from Bacillus subtilis natto. Peptide sequences were analyzed by sophisticated MS-MS analysis, performed with a pair of two surfactins with different fatty acid substitutions. Fragment peaks were divided into two series; one was a series of the ions which carried fatty acid, and thus were characterized by the fatty acid mass difference, and the other was a series of the ions which consisted of pure peptide and thus showed a superimposable pattern between a pair of surfactins.View full abstractDownload PDF (470K)
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