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Volume 46, Issue 2
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Masanori SOMEI, Fumio YAMADA, Gaku YAMAMURA1998 Volume 46 Issue 2 Pages 191-198
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA simple synthetic method for 5H-pyrido[4, 3-b]indole (γ-carboline) derivatives having a methoxycarbonyl group at the 4-position was developed based on 1-hydroxyindole chemistry. By applying the method, various 3-substituted metyl 5H-pyrido[4, 3-b]indole-4-carboxylates and 2-substituted methyl 2, 3-dihydro-3-oxo-5H-pyrido[4, 3-b]indole-4-carboxylates were prepared.View full abstractDownload PDF (1344K) -
Yumiko SUZUKI, Yuki TAKEMURA, Ken-ichi IWAMOTO, Takeo HIGASHINO, AKira ...1998 Volume 46 Issue 2 Pages 199-206
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS4-(α-Benzyl-α-hydroxybenzyl)quinazoline (4a) underwent retro-benzoin condensation catalyzed by cyanide ion to give deoxybenzoin (2a) and quinazoline (5a). Similarly, several nitrogen-containing heteroarenes (4, 9, 12, 16-19) having an α-hydroxybenzyl group at the α-position of the nitrogen underwent retro-benzoin type condensation to afford ketones (2) and heteroarenes (5). However, similar reaction of pyrazolopyrimidines (13, 14, 15) having an α-benzyl-α-hydroxybenzyl group resulted in benzyl migration, giving benzylpyrazolopyrimidines (8) and arenecarbaldehydes (3). Tetrabutylammonium cyanide (11, Bu4NCN) was a more effective cyanide ion donor than KCN (10). The retro-benzoin condensation was applied to the synthesis of 2-substituted quinazolines (38) from 2-chloro-4-aroylquinazolines (34), using the aroyl group as a protecting and electron-withdrawing group.View full abstractDownload PDF (1235K) -
Takashi MICHIDA, Yumiko YAMAOKA1998 Volume 46 Issue 2 Pages 207-210
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCathodic reductions of phenazine (1) and 2, 7-diethoxyphenazine (2) were carried out in acetonitrile containing trifluoroacetic acid (TFA) under air, and 2-(cyanomethy)phenazine (3) and 2-(cyanomethyl)-3, 8-diethoxyphenazine(4) were obtained as final products, respectively. Cyclic voltammetry (CV) of 1 and 2 showed two cathodic peaks and these peaks had counterparts under N2 and/or air. When CV was carried out under air, the current of the second cathodic peak of 2 was increased. Controlled potential electrolysis (CPE) of 1 under N2 at the second cathodic peak gave a value of 1.8 for n(faradays per mole of substance electrolyzed) and 84% of the starting compound was recovered.Dihydrophenazines produced by the electrochemical reduction of 1 and 2, activated dissolved oxygen. The activated oxygen oxidized the solvent, i.e., acetonitrile, and gave a cyanomethyl radical, which attacked the 2-position of 1 and 2 to give 3 and 4, respectively. MO calculations of three putative intermediates were conducted to obtain their localization energy and heat of formation. The heat of formation of the intermediate radical appears to decide the direction of the reaction.View full abstractDownload PDF (598K) -
Haruhiro FUJIMOTO, Yuji SATOH, Mikio YAMAZAKI1998 Volume 46 Issue 2 Pages 211-216
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new sesterterpenetriol named kobiin and three new 2-furanones named kobifuranones A, B, and C were isolated from an Ascomycete, Gelasinospora kobi. Kobiin, the main immunosuppressive principle of this fungus, possesses a bicyclic skeleton of five- and fifteen-membered rings. Kobifuranones A, B, and C were supposed to be metabolites formed from a common intermediate biosynthesized through the acetate-malonate pathway. The immunosuppressive activity of kobiin and kobifuranones A, B, and C was evaluated in a system of mouse spleen lymphocytes stimulated to proliferate with concanavalin A and lipopolysaccharide.View full abstractDownload PDF (822K) -
Naoyoshi MAEZAKI, Takeshi SHOGAKI, Masashi UCHIDA, Katsuya TOKUNO, Tsu ...1998 Volume 46 Issue 2 Pages 217-221
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1, 6-Asymmetric induction was achieved in the acid-induced diastereoselective acetal cleavage reaction of a 4-substituted bicyclic acetal 8 bearing a chiral sulfinyl group. On treatment with titanium tetrachloride and 2, 6-disubstituted pyridine bases, 8 gave a synthetically versatile 3, 3-disubstituted dihydropyran derivative 9a with moderate diastereoselectivity. The utility of this chiral synthon was successfully demonstrated by a formal synthesis of (-)-frontalin.View full abstractDownload PDF (806K) -
Tokunaru HORIE, Kenichi SHIBATA, Kazuyo YAMASHITA, Kenichi FUJII, Masa ...1998 Volume 46 Issue 2 Pages 222-230
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2', 4'-Bis(benzyloxy)-3', 6'-dimethoxychalcones (5), which were obtained from the dibenzyl ether of 2, 4-dihydroxy-3, 6-dimethoxyacetophenone (3), were oxidatively rearranged with thallium (III) nitrate in methanol and the resultant products were converted into 7-hydroxy-5, 8-dimethoxyisoflavones (8) by hydrogenolysis, followed by cyclization. The isoflavones were quantitatively demethylated to 5, 7-dihydroxy-8-methoxyisoflavones (2) via their acetates. The isomeric 5, 7-dihydroxy-6-methoxyisoflavones (1) were also synthesized from the chalcones, obtained from 2, 3-dimethoxy- (16) or 2-isopropoxy-3-methoxy-4, 6-bis(benzyloxy)acetophenones (21), by a similar method. On the other hand, the isoflavones with two hydroxy groups at the 2'- and 4'-positions were easily synthesized by the following method. Treatment of the rearranged product from 2, 2', 4, 4'-tetrakis(bezyloxy)-3', 6'-dimethoxychalcone (5f) with hydrochloric acid (HCl) in acetic acid afforded 2', 4', 7-tris(benzyloxy)-5, 8-dimethoxyisoflavone (10f). The 5-methoxy group in the isoflavone was quantitatively cleaved to give the corresponding 5-hydroxyisoflavone (11f), which was isomerized to 2', 4', 7-tris(benzyloxy)-5-hydroxy-6-methoxyisoflavone (25f) in the presence of anhydrous potassium carbonate. Hydrogenolysis of the two 5-hydroxyisoflavones proceeded smoothly to give 2', 4', 5, 7-tetrahydroxy-8-(2f) and 6-methoxyisoflavones(1f), respectively. The 13C-NMR spectra of these isoflavones supported the proposed structures of polyhydroxyisoflavones. The proposed structures of two natural isoflavones were revised.View full abstractDownload PDF (1196K) -
Rong XU, Meng-Kwoon SIM, Mei-Lin GO1998 Volume 46 Issue 2 Pages 231-241
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of tropinyl and piperidinyl esters was synthesized and evaluated for inhibitory activities on the endothelial muscarinic receptors of rat (M3) and rabbit (M2) aorta. Some of the esters (cyclohexylphenylglycolates and cyclohexylphenylpropionates) were found to be better antimuscarinic compounds than standard M2 and M3 inhibitors such as AFDX116 and 4-diphenylacetoxy-N-methylpiperidine (DAMP), with pKEC50 values in the range of 8-9. A few esters were found to be more selective M3 than M2 inhibitors, but these tended to have low activities. The hydrophobic, electronic and steric characteristics of these esters were correlated with antimuscarinic activity by using appropriate parameters representing hydrophobicity (HPLC capacity factor, log kw), size (molecular volume) and electronic character (Taft's polar substituent constant σ* and 13C chemical shift difference Δδ). Finally, 92% of the M2-inhibitory activities of the esters could be accounted for by the size and electronic character σ* of the side chain. In contrast, the M3-inhibitory activities of these esters were mainly attributed to the electronic nature (σ*, Δδ) of the side chain, with good activity being associated with electron-withdrawing groups. Visualization of the comparative molecular field analysis (CoMFA) steric and electrostatic fields provided further confirmation of the structure-activity relationship (SAR) derived from traditional quantitative structure-activity relationship (QSAR) approaches.View full abstractDownload PDF (1623K) -
Hirokazu KUBOTA, Akio KAKEFUDA, Hitoshi NAGAOKA, Osamu YAMAMOTO, Ken I ...1998 Volume 46 Issue 2 Pages 242-254
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn the course of our research on spiro-compounds as neurokinin receptor antagonists, N-[2-aryl-4-(spiro-substituted piperidin-1'-yl)butyl]carboxamides were designed, based on YM-35375 (3) as a lead compound, and evaluated for NK2 receptor-antagonistic activities. Some derivatives inhibited the binding of radio-labeled neurokinin A to the NK2 receptor with IC50 values at the level of 10-9M. Among these compounds, (±)-1'-[4-(N-benzoyl-N-methylamino)-3-(3, 4-dichlorophenyl)butyl]spiro[benzo[c]thiophene-1(3H), 4'-piperidine] 2-oxide (58, YM-38336) showed 10 times more potent NK2 receptor binding affinity than compound 3 (IC50 values of 8.9 and 84nM, respectively). It showed more potent inhibitory activity (ID50 20μg/kg (i.v.)) against [β-Ala8]-NKA(4-10)-induced bronchoconstriction in guinea pigs than compound 3 (ID50 41μg/kg (i.v.)). This compound was also effective intraduodenally in the same model, exhibiting an ID50 value of 0.41μg/kg.View full abstractDownload PDF (1662K) -
Fumio ITOH, Yuji NISHIKIMI, Atsushi HASUOKA, Yoshio YOSHIOKA, Koichi Y ...1998 Volume 46 Issue 2 Pages 255-273
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of TAN-1511 analogues bearing a non-peptide spacer in place of the Gly-Gly-Gly sequence in the peptide moiety was synthesized, and the effects of these compounds on the proliferation of bone marrow cells in culture and experimental leukocytopenia in mice were examined. The structure-activity relationships obtained were as follows. As the substituent at the 2-position of the 4-thiaheptanoic acid framework, an amino group, methyl group or hydrogen was preferable; as a spacer in place of the Gly-Gly-Gly sequence, a 4-aminobenzoyl or 4-aminomethylbenzoyl group was suitable; and as the fatty acids bonded to the 6, 7-dihydroxy groups, C16 fatty acid was best. Compounds 12f, 30d and 30i potently promoted the proliferation of bone marrow cells in culture and the restoration of leukocyte counts in a murine leukocytopenia model.View full abstractDownload PDF (2688K) -
Chisako YAMAGAMI, Nami KISHIDA, Shuei KA, Motoko HORIUCHI, Noriko MOTO ...1998 Volume 46 Issue 2 Pages 274-278
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe π values of benzalacetones (BZ) and trans-1, 1, 1-trifluoro-4-phenyl-3-buten-2-ones (TF) with a substituent on the benzene ring were analyzed by the directional Hommett-type treatment. The correlation equation showed that πBZ and πTF values are altered from the π value of monosubstituted benzenes, πPhX, mainly by the change in the hydrogen bonding behavior of the variable substituent caused by the electron-withdrawing fixed substituent. The log k' values for BZ and TF derived from reversed-phase liquid chromatography (RPLC) were correlated with log P values determined by using different compositions of methanol-phosphate buffer (pH 7.4) as eluents. A good linear correlation was obtained at 50% methanol concentration.View full abstractDownload PDF (738K) -
Kiyoshi TSUJI, Katsuya NAKAMURA, Takashi OGINO, Nobukiyo KONISHI, Taka ...1998 Volume 46 Issue 2 Pages 279-286
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of novel 5-substituted-2, 3-diarylthiophenes has been synthesized and found to be active in the rat adjuvant arthritis (AA) model and/or in the yeast-induced hyperalgesia (Randall-Selitto) assay. Among the compounds synthesized herein, 2-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)thiophene (6a) exhibited the most potent activities on AA, collagen-induced arthritis (CIA) and the delayed-type hypersensitivity response to type II collagen. 5-Bromo-2-[4-(methylamino)phenyl]-3-[4-(methylsulfinyl)phenyl]thiophene (38) is also a potent inhibitor of AA, CIA, hyperalgesia and in vitro tumor necrosis factor-α production.View full abstractDownload PDF (1286K) -
Toshio OKAZAKI, Akira SUGA, Toshihiro WATANABE, Kazumi KIKUCHI, Hiroyu ...1998 Volume 46 Issue 2 Pages 287-293
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2, 7-Diethyl-5H-pyrazolo[1, 5-b][1, 2, 4]triazole derivatives were synthesized and evaluated for activity as angiotensin II receptor antagonists. Replacement of the C-6 hydrogen with C-linked oxygen functional groups led to derivatives with increased in vitro activities. Among these compounds, 2, 7-diethyl-5-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-5H-pyrazolo[1, 5-b][1, 2, 4]triazole-6-carboxylic acid (2d) showed potent, insurmountable antagonism, but had poor oral potency against angiotensin II-induced pressor response in rats. In order to improve the oral activity, the carboxylic acid function of 2d was converted into a double ester. This modification afforded (±)-1-[(ethoxycarbonyl)oxy]ethyl 2, 7-diethyl-5-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-5H-pyrazolo[1, 5-b][1, 2, 4]triazole-6-carboxylate (2f), which was orally active in rats, and produced a dose-dependent decrease in blood pressure when administered orally to conscious furosemide-treated dogs, with ca. 3-fold increased potency in comparison with the parent C-6 hydrogen compound.View full abstractDownload PDF (986K) -
Akiko NISHIMURA, Mitsutomo TSUHAKO, Tetsuro MIKI, Toshio OGIHARA, Yosh ...1998 Volume 46 Issue 2 Pages 294-297
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCapillary electrophoresis with laser-induced fluorescence detector (CE-LIF) was successfully applied to the analysis of the variable number of tandem repeats (VNTR) in a human apolipoprotein B gene (APOB). Apolipoprotein B VNTR alleles containing more than 35 repeat units are a significant risk factor for heart disease. Thus, we developed a method for accurately determining the number of repeat units (16 bp) in the VNTR using capillary electrophoresis. The CE-LIF technique gave excellent resolution of APOB alleles differing by 2 or 4 repeat units over the range 600 to 1000 bp.The recommended conditions for the analysis of APOB VNTR loci by CE-LIF are as follows : effective length of capillary (100μm i.d., 360μm o.d.), 50cm; running buffer, 50mM Tris-borate 0.5% methylcellulose and 0.1μM fluorescent dye YO-PRO-1; electric field, 150V/cm.View full abstractDownload PDF (675K) -
Yoshihiro MIMAKI, Minpei KURODA, Aiko KAMEYAMA, Akihito YOKOSUKA, Yuta ...1998 Volume 46 Issue 2 Pages 298-303
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhytochemical examination of the underground parts of Ruscus aculeatus has led to the isolation of a total of twelve steroidal saponins, including seven new ones. The structures of the new saponins were determined by spectroscopic analysis and chemical evidence. The furostanol saponin, having a diglycoside moiety modified with a (2S, 3S)-2-hydroxy-3-methylpentanoic acid group and an acetic acid group, and its corresponding spirostanol saponin exhibited cytostatic activity on leukemia HL-60 cells.View full abstractDownload PDF (937K) -
Makiko FUJII, Junko MORIYAMA, Noriko HAMAZUMI, Mitsuo MATSUMOTO1998 Volume 46 Issue 2 Pages 304-308
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe release of acetaminophen (AAP) from tablets containing phospholipids was examined using hydrogenated soybean phospholipid (HSL) and its main components, phosphatidylcholine (PC), phosphatidylethanolamine (PE) and phosphatidylinositol (PI), although the PI was not well purified (PI rich). Tablets compressed with 400kgf had about 9% porosity and 2-4kgf hardness. The release patterns of AAP from the tablets were fitted to Higuchi's square root of time law. The release rate was influenced by the pH of the medium, though solubility of AAP did not change with pH. PC tablets showed faster release at pH of less than 3 than that at pH of above 3, whereas PI rich and HSL tablets showed faster release at pH of above 3 than that at pH of less than 3. The release rate from PE tablets was little affected by pH. A linear relationship exists between the release rate of AAP and the rate of water absorption by the tablet. The ionization state of the phospholipids changes with the pH of the medium, and affects the hydration characteristics. The fully ionized state, at pH of less than 3 in the case of PC and above 3 in the case of PI is most effective on hydration. PE does not fully ionize because of intermolecular hydrogen bonding.View full abstractDownload PDF (669K) -
Tohru AMEMIYA, Satoshi MIZUNO, Hiroaki YUASA, Jun WATANABE1998 Volume 46 Issue 2 Pages 309-313
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSScreening of surfactants was carried out to develop an oil in water (o/w) emulsion type new vehicle for a soft gelatin capsule (SGC), using polyethyleneglycol 400 (PEG 400) as hydrophilic phase and medium chain triglyceride (Miglyol 810[○!R]), propyleneglycol dicaprylate (Sefsol 228[○!R]) or soybean oil as hydrophobic phase (PEG 400 : hydrophobic phase : surfactant=87 : 10 : 3) and by means of simple homogenization.Polyoxyethylene (20) cetylether (BC-20TX[○!R]), which can form homogeneous and viscous white gels using the above hydrophilic and hydrophobic phase combination, was selected as a model surfactant for developing the new vehicle. Using Miglyol 810[○!R] as hydrophobic phase, a model new vehicle formulation (PEG 400 : water : Miglyol 810[○!R] : BC-20TX[○!R]=77 : 10 : 10 : 3) was prepared, and its physicochemical properties were evaluated.The particle size distribution of the new vehicle, after diluting about 3000 times with water, ranged from about 0.5 to 50μm. Furthermore, the new vehicle had thixotropic property at room temperature (about 25°C) and temperature-dependent gel-sol transforming property with the transformation temperature of about 37°C.These properties meet the requirement for encapsulation of the new vehicle in SGC and suggest that it can be expected to form the o/w emulsion state in the aqueous environment in the stomach. The rheological properties would also make it advantageous for use in other dosage forms such as suppository, cataplasm or liniment.View full abstractDownload PDF (886K) -
Kazuhiro MATSUMOTO, Yoshinobu NAKAI, Etsuo YONEMOCHI, Toshio OGUCHI, K ...1998 Volume 46 Issue 2 Pages 314-318
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of pore size on the gaseous adsorption of ethenzamide (EZ) on porous crystalline cellulose (PCC) in a mixture of PCC-EZ, and the physicochemical stability of EZ in a mixture of PCC-EZ after storage at various relative humidities (RHs) were investigated by powder X-ray diffractometry, differential scanning calorimetry, specific surface area and pore size distribution measurements. After heating a mixture of PCC-EZ, which contained less than 7% EZ, at 70°C at reduced pressure, the EZ became amorphous. The specific surface areas and pore size distribution curves of PCC and the heated mixtures of PCC-EZ were calculated from the nitrogen gas adsorption isotherms. The specific surface area of PCC was 82.3m2/g, while the specific surface areas of the heated mixtures of PCC-3% EZ, PCC-5% EZ and PCC-7% EZ were 74.1, 72.7 and 63.8m2/g, respectively. The specific surface area of the heated mixture of PCC-EZ decreased with an increase in the mixing ratio of EZ. In the pore size distribution curves of the heated mixtures of PCC-EZ, the pore volumes in the range of pore diameters from 2 to 40nm decreased compared with the pore volume of PCC. The volumes of pores with diameters ranging from 3 to 10nm decreased markedly with an increase in the mixing ratio of EZ. These results indicate that the adsorption of EZ on the pore surfaces of PCC occurred principally in the range of diameters from 3 to 10nm. After storage of the heated mixtures of PCC-7% EZ at various RHs for 7d at 30°C, recrystallization of EZ was observed in the X-ray diffraction spectrum when the mixtures were stored above RH 72.8% due to condensation of water vapor in pores.View full abstractDownload PDF (739K) -
Yasuyo OKADA, Kyoko KOIZUMI1998 Volume 46 Issue 2 Pages 319-323
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree positional isomers of 61, 6n-di-O-α-D-glucosyl-cyclomaltoheptaose [1, n-(G)2-βCDs; n=2-4] which existed in the digests with glucoamylase of the products from cyclomaltoheptaose (β-cyclodextrin, βCD) and maltose with Klebsiella pneumoniae pullulanase, were purified by HPLC. The solubilities of two isomers of those doubly branced βCDs, 1, 2- and 1, 3-(G)2-βCDs, in water were much higher than those of parent non-branched βCD and mono-branched βCD, 6-O-α-D-glucosyl-βCD (G-βCD), while the solubility of another isomer, 1, 4-(G)2-βCD, was significantly lower than these two isomers, though it was higher than that of βCD. On the other hand, the solubilities of 1, 2- and 1, 3-isomers in 10, 30, and 50% (v/v) aqueous methanol at 25°C were independent of methanol concentrations and their solubilities were the same as those in water at 25°C. However, that of 1, 4-isomer increased with increasing methanol concentrations. The hemolytic activities of 1, n-(G)2-βCDs on human erythrocytes in isotonic solution were lower than those of G-βCD and βCD, and became weaker in the order of 1, 4->1, 2->1, 3-isomers. The complex-forming abilities of 1, n-(G)2-βCDs for digitoxin, digoxin, fluorometholone, flurbiprofen, hydrocortisone acetate, and norfloxacin were about the same as those of βCD and G-βCD, whereas reserpine was more difficult to include within 1, n-(G)2-βCDs than βCD and G-βCD. Nevertheless, the solubilities of those guest compounds were much more enhanced by 1, n-(G)2-βCDs and G-βCD than by βCD.View full abstractDownload PDF (658K) -
Masazumi KOJIMA, Shuichi ANDO, Katsuo KATAOKA, Toyohiko HIROTA, Kazuha ...1998 Volume 46 Issue 2 Pages 324-328
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe swelling and water mobility in directly compressed tablets of micronized low-substituted hydroxy-propylcellulose (LH41) were studied by magnetic resonance imaging (MRI), in comparison with those in tablets of hydroxypropylcellulose (HPC) and hydroxypropylmethylcellulose (HPMC). Images of a hydrating LH41 tablet showed that the contrast of the outer moiety of the tablet became slightly brighter in the coronal and transverse planes. A transverse image of the LH41 tablet showed that swelling, deformation and cracking occurred on the edge of the tablet. Images of hydrating HPC and HPMC tablets clearly showed an interface layer between the dry core and the swollen gel layer. Imaging data analyses showed that overall swelling of the tablets decreased as follows : HPMC>HPC»LH41; the amount of absorbed water also decreased in this order. The three kinds of tablets expanded in the transverse section much more than in the coronal direction. The spin-spin relaxation time (T2) of water in the LH41 tablet was much smaller than that of free water, indicating that the water is located in a highly restricted environment and suggesting that strong interaction occurs between the absorbed water and the polymer. The apparent self-diffusion coefficient (ADC) of water absorbed into the LH41 tablet was smaller than that of free water, indicating that the water diffusivity is restricted in the polymer matrix. In the other two tablets, nearly the same tendency was observed for T2 and ADC. The T2 analyses of the water components in almost the whole coronal section of the hydrating tablets revealed that one type of water existed in the LH41 tablet and that two types of water with different mobility existed in the HPC and HPMC tablets. These results indicate that the gel layer properties may be different among the three hydrophilic polymers.View full abstractDownload PDF (1011K) -
Yoshio MATSUBARA, Kazutada KITANO, Takayuki YAMAMOTO, Toshihisa MAESHI ...1998 Volume 46 Issue 2 Pages 329-331
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNew 2-monosubstituted and 2, 2-disubstituted 2, 3-dihydro-3, 5-diphenyl-1, 3, 4-thiadiazoles (2) were synthesized by the reaction of N'-phenylthiobenzoylhydrazide with aliphatic, aromatic and heterocyclic aldehydes and ketones in the presence of trimethylsilyl chloride in benzene. The reaction proceeded smoothly to afford the corresponding 1, 3, 4-thiadiazoles (2a-2j) in excellent yields (84-96%) except for a few cases, such as the 5-methyl-2-furfural and 2-acetylthiophene systems. 2, 3-Dihydro-2, 2-dimethyl-3, 5-diphenyl-1, 3, 4-thiazole (2f) showed curative activity against powdery mildew of wheat.View full abstractDownload PDF (508K) -
Junko KOYAMA, Izumi TOYOKUNI, Kiyoshi TAGAHARA1998 Volume 46 Issue 2 Pages 332-334
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe Diels-Alder reaction of 1, 2, 3-benzotriazine with several pyrrolidine enamines of carbonyl compounds was carried out in chloroform in the presence of zinc bromide to afford 2- or 3-mono-, or 2, 3-disubstituted quinolines. This method was applied to the synthesis of the alkaloids, 2-propylquinoline and 2-pentylquinoline.View full abstractDownload PDF (475K) -
Shino MANABE1998 Volume 46 Issue 2 Pages 335-336
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe [2, 3] sigmatropic rearrangement of α-propargyloxyacetic acids was achieved by the use of BuLi-(-)-sparteine complex in toluene. BuLi-chiral ligand complexes are stronger bases than lithium amides, so they are expected to be good mediators of this reaction.View full abstractDownload PDF (425K) -
Toshiaki YAMAGUCHI, Takashi YANAGI, Hiroshi HOKARI, Yuko MUKAIYAMA, Te ...1998 Volume 46 Issue 2 Pages 337-340
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFor large-scale synthesis of monocalcium bis[(2S)-2-benzyl-3-(cis-hexahydroisoindolin-2-ylcarbonyl)propionate]dihydrate (1, KAD-1229), we investigated regioselective reactions of (S)-2-benzylsuccinic acid (2) with cis-hexahydroisoindoline (4). It was difficult to obtain a half amide regioselectively through coupling reaction of the (S)-acid 2 with the amine 4. Therefore, the succinic acid 2 was converted to bis-activated esters 3a-c and these were reacted with 4 to give the amides 5a-c in good yields, regioselectively. The amides 5a-c were derived to KAD-1229, which has a potent hypoglycemic effect, in good yields.View full abstractDownload PDF (628K) -
Chihiro ITO, Shinya KATSUNO, Hiroshi FURUKAWA1998 Volume 46 Issue 2 Pages 341-343
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new furocoumarins named lansiumarin-A (1), -B (2), and -C (6) were isolated from the branches of Clausena lansium (Rutaceae), and their structures were elucidated by chemical and spectroscopic methods.View full abstractDownload PDF (482K) -
Chihiro ITO, Shinya KATSUNO, Nijsiri RUANGRUNGSI, Hiroshi FURUKAWA1998 Volume 46 Issue 2 Pages 344-346
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree novel carbazole alkaloids, named clausamine-A (1), -B (2), and -C (3) were isolated from Clausena anisata (Rutaceae) collected in Thailand, and their structures were elucidated by means of spectroscopic analyses. All these novel carbazoles have 1-oxygenated 3, 4-disubstituted structures with a lactone moiety. This is the first report of the isolation of lactonic carbazole alkaloids from a natural source.View full abstractDownload PDF (546K) -
Mitsuko MAEDA, Yasuhiro IZUNO, Koichi KAWASAKI, Yoshihisa KANEDA, Yu M ...1998 Volume 46 Issue 2 Pages 347-350
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAnalogs of a partial sequence peptide of laminin, i.e., Tyr-Ile-Gly-Ser-Arg (YIGSR) analogs and Cys-Asp-Pro-Gly-Tyr-Ile-Gly-Ser-Arg (CDPGYIGSR) analogs, were prepared by the solid-phase method and their inhibitory effects on experimental metastasis of B16-BL6 melanoma cells were examined. YIGSR analogs in which Ile was replaced by other hydrophobic amino acids (Met, Leu, Phe) were inhibitory. Cys-containing analogs of YIGSR were also prepared, but were less active than the parent peptide, YIGSR. Among them, CYIGSR was easily oxidized to form a disulfide bond. A Cys-containing YIGSR analog cyclized through a disulfide bond, cyclo(CYIGSRC)G, was prepared. The disulfide bond formation was performed on the resin by the silyl chloride-sulfoxide method and by the iodine oxidation method. The yield of the silyl chloride-sulfoxide method was much better than that of the iodine oxidation method.View full abstractDownload PDF (647K) -
Hirokazu KUBOTA, Masahiro FUJII, Ken IKEDA, Makoto TAKEUCHI, Tadao SHI ...1998 Volume 46 Issue 2 Pages 351-354
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAnalysis of the structural requirements of compound 1 (SR48968), a potent NK2 receptor antagonist, revealed that the 4-phenyl group of the piperidine is essential for binding with the NK2 receptor and occupies an equatorial position. Energy calculation of a variety of substituted 4-phenyl piperidines revealed that spiro[isobenzofuran-1(3H), 4'-piperidine] possesses a conformationally restricted equatorial phenyl group. Our compound 12 (YM-35375) possessing this spiro-substituted piperidine bound to the NK2 receptor with an IC50 value of 84nM and to NK1 receptor with an IC50 value of 710nM. It showed more potent inhibitory activity (ID50 41μg/kg (i.v.)) against [β-Ala8]-NKA(4-10)-induced bronchoconstriction in guinea pigs than (±)-SR48968 (ID50 68μg/kg (i.v.)). YM-35375 may be a new lead compound for novel NK2 receptor antagonists or NK1-NK2 dual antagonists.View full abstractDownload PDF (744K) -
Pengyue SUN, Yingjie CHEN, Noriko SHIMIZU, Tadahiro TAKEDA1998 Volume 46 Issue 2 Pages 355-358
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new flavonol glycoside, epimedin I (1), a new chromone, 5, 7-dihydroxy-2-(p-hydroxy-phenoxy)-6-prenyl-chromone (2), and icariside A7 (3) were isolated from the aerial parts of Epimedium koreanum NAKAI (Berberidaceae) together with six known compounds, chaohuoside A (epimedin L) (4), 8-prenylkaempferol (5), anhydroicaritin (6), ginkgetin (7), isoginkgetin (8) and bilobetin (9). Their structures were established by spectroscopic methods and chemical evidence.View full abstractDownload PDF (654K) -
Tsuyoshi IKEDA, Manabu UDAYAMA, Masafumi OKAWA, Tomonori ARAO, Junei K ...1998 Volume 46 Issue 2 Pages 359-361
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs a part of our studies of hepatoprotective drugs, we prepared some soyasapogenol B analogs from soyasaponin I. We examined the hepatoprotective effects of these analogs, using immunologically-induced liver injury, in primary cultured rat hepatocytes. Soyasaponin III and soyasapogenol B monoglucuronide were more effective than soyasaponin I. Both compounds were significantly effective even at 30μM. The action of soyasapogenol B was almost equal to that of soyasaponin I, although glucuronic acid did not show any activity even at the highest dose (500μM). When the two compounds were mixed, the hepatoprotective action did not change, compared with soyasapogenol B. Therefore, we concluded that the linkage between glucuronic acid and soyasapogenol B could enhance the hepatoprotective activity.View full abstractDownload PDF (547K) -
Masayuki TAKAHIRA, Akiko KUSANO, Makio SHIBANO, Genjiro KUSANO, Nobuko ...1998 Volume 46 Issue 2 Pages 362-365
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new fukiic acid esters, cimicifugic acids A (1), B (2), and C (3), were isolated along with fukinolic acid (4), fukiic acid (5), caffeic acid (6), ferulic acid (7), isoferulic acid (8), 3, 4-dimethoxycinnamic acid (9) and p-coumaric acid (10) from Cimicifuga simplex. Their structures were identified as 2-feruloyl, 2-isoferuloyl, and 2-p-coumaroyl fukiic acid (1-3) on the basis of spectroscopic and chemical data.View full abstractDownload PDF (685K) -
Hiroshi NAGASE, Jun HAYAKAWA, Kuniaki KAWAMURA, Kouji KAWAI, Yuko TAKE ...1998 Volume 46 Issue 2 Pages 366-369
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new type of K-agonist, 17-cyclopropylmethyl-3, 14β-dihydroxy-4, 5α-epoxy-6β-[N-methyl-trans-3-(3-furyl)acrylamido]morphinan hydrochloride (1, TRK-820), was discoverd by a new working hypothesis. The "message-address concept" for opioid antagonists and the "accessory site" for general antagonists were applied to design TRK-820. A unique structural feature of TRK-820, which is different from other prototypical K-opioid receptor agonists, is the existence of the 4, 5-epoxymorphinan structure with a tyrosine-glysine moiety for endogenous opioid peptides such as dynorphins. TRK-820 exhibited high potency and high K-selectivity in guinea pig ileum (GPI) and mouse vas deferens (MVD) preparations. In the mouse acetic-acid-induced writhing model and mouse tail flick model of antinociception, TRK-820 was 85-140 times more potent than morphine and 85-350 times more potent than U-50488H. This structurally novel K-agonist showed neither aversion nor preference in the Conditioned Place Preference test, in spite of the fact that prototypes of K-agonists (U-50488H derivatives) demonstrated aversion.View full abstractDownload PDF (584K) -
Tian-Shung WU, Yu-Yi CHAN, Yann-Lii LEU1998 Volume 46 Issue 2 Pages 370-372
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo novel compounds, aristolide-A(1) and -B(2) were isolated from the root and stem of Aristolochia heterophylla HEMSL. Their structures were determined by spectral analysis. This is the first instance of the isolation of dihydrophenanthrenelactones from a natural source.View full abstractDownload PDF (399K) -
Hirotatsu KOJIMA, Kuniko SAKURAI, Kazuya KIKUCHI, Shigenori KAWAHARA, ...1998 Volume 46 Issue 2 Pages 373-375
Published: February 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEndogenous nitric oxide (NO) appears to modulate many physiological and pathophysiolgoical processes. In order to obtain direct evidence for NO functions in vivo, we have developed 4, 5-diaminofluorescein (DAF-2) as a novel fluorescent indicator for NO. Green-fluorescent triazolofluorescein formed by the reaction of NO and DAF-2 affords high sensitivity for NO (detection limit : 5 nM). Membrane-permeable DAF-2 diacetate (DAF-2DA) was loaded into activated rat aortic smooth muscle cells, where the ester bonds are hydrolyzed by intracellular esterase, generating DAF-2. The fluorescence in the cells increased in a NO concentration-dependent manner. This imaging method should be useful for studies of the dynamic biological actions of NO at the molecular level with fine temporal and spatial resolution.View full abstractDownload PDF (548K)
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