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Volume 43, Issue 4
Displaying 1-35 of 35 articles from this issue
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Hartmut LAATSCH, Bernd RENNEBERG, Ulf HANEFELD, Michael KELLNER, Heinz ...1995 Volume 43 Issue 4 Pages 537-546
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAntitumor, antimicrobial, and phytotoxic activities of the marine antibiotic pentabromopseudilin (1a) and related phenyl-, benzyl- and benzoyl pyrroles were compared. All activities depended strongly on the substituent pattern, with the natural compound 1a being the most active one. As judged from model reactions, a covalent bond of nucleophiles to the pyrrole system may be involved in the inhibition of macromolecular syntheses.View full abstractDownload PDF (1152K) -
Haruhiro FUJIMOTO, Yuji SATOH, Megumi NAKAYAMA, Tomoe TAKAYAMA, Mikio ...1995 Volume 43 Issue 4 Pages 547-552
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFive new components, named multiforisins A, B, C, D, and E, with immunosuppressive activity were isolated from an Ascomycete, Gelasinospora multiforis. Multiforisin A, the main immunosuppressive principle of this fungus, was deduced to be 5-formyl-3-(hydroxymethyl)-4-methoxy-6-(1E-propenyl)-α-pyrone. Multiforisins B, C, D, and E were also deduced to be α-pyrone derivatives related to multiforisin A. The IC50 values of multiforisins A, B, C, D, E, and dihydro multiforisin A were evaluated against proliferation of mouse spleen lymphocytes stimulated with concanavalin A and lipopolysaccharide.View full abstractDownload PDF (789K) -
Machiko ONO, Yasuo YAMAMOTO, Hiroyuki AKITA1995 Volume 43 Issue 4 Pages 553-558
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour bisabolane sesquiterpenes, (±)-curcudiol (2), (±)-curcuphenol (3), (±)-curcuhydroquinone (5) and (±)-curcuquinone (6), were synthesized based on the reaction of methyl 4, 5-epoxy-(2E)-pentenoate (1) with methoxytoluenes in the presence of boron trifluoride etherate.View full abstractDownload PDF (909K) -
Yoshiji TAKEMOTO, Shigeo UEDA, Jun TAKEUCHI, Takahisa NAKAMOTO, Chuzo ...1995 Volume 43 Issue 4 Pages 559-563
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe LiClO4-catalyzed cycloaddition reaction of 1-azatriene iron-tricarbonyl complex with Danishefsky's diene proceeds in a highly stereoselective manner to give a diastereomerically pure 2-substituted dehydropiperidinone derivative. The stereochemistry of the major cycloadduct was determined to be 6RS, 1'SR by X-ray cyrstallographic analysis.View full abstractDownload PDF (876K) -
Kinuko TERADA, Chie HONDA, Kiyoko SUWA, Shizuyo TAKEYAMA, Hisae OKU, W ...1995 Volume 43 Issue 4 Pages 564-566
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new acetylenic compounds, compounds I, II and III were isolated from the cultured cells of Asparagus offcinalis L. (Liliaceae) and their structures identified as 1-methoxy-4-[5-(4-methoxyphenoxy)-3-penten-1-ynyl]-benzene, 4-[5-(4-methoxyphenoxy)-3-penten-1-ynyl]phenol and 4-[5-(4-hydroxyphenoxy)-3-penten-1-ynyl]phenol, respectively, from chemical and spectral analysis.View full abstractDownload PDF (539K) -
Naoki NODA, Ryuichiro TANAKA, Kazushige TSUJINO, Machiko MIURA, Kazumo ...1995 Volume 43 Issue 4 Pages 567-570
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSix amphoteric galactocerebrosides were isolated from the land annelid (Hirudo nipponica). Two of them have a tri-unsaturated long-chain base, D-erythro-(4E, 8Z, 11Z)-docosasphingatrienine. The position and geometry of the double bonds in the long-chain base unit were determined on the bases of chemical and spectral data.View full abstractDownload PDF (619K) -
Yoshiji TAKEMOTO, Taiichi OHRA, Kenji SUGIYAMA, Takeshi IMANISHI, Chuz ...1995 Volume 43 Issue 4 Pages 571-577
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn optically active vinylic sulfoxide bearing a leaving group at the γ-position was stereoselectively transformed into a chiral cyclopropane by means of a Michael addition with an allylmagnesium bromide. The Michael induced ring-closure reaction requires both allylmagnesium bromide as a uncleophile and chloride as a leaving group for high diastereoselectivity. The absolute stereochemistry of the cycloadduct was confirmed by X-ray analysis.View full abstractDownload PDF (1205K) -
Kazuko YOSHIKAWA, Hiroshi KINOSHITA, Yukiko KAN, Shigenobu ARIHARA1995 Volume 43 Issue 4 Pages 578-581
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSix new dihydrobenzofuran neolignans were isolated from the fresh rhizomes of Coptis japonica var. dissecta, together with (+)-isolariciresinol, (+)-lariciresinol glucoside, (+)-pinoresinol, (+)-pinoresinol glucoside, (+)-syringaresinol glucoside and ethyl ferulate. Their structures were determined on the basis of spectroscopic data and chemical evidence. Their absolute configurations were determined by means of CD studies.View full abstractDownload PDF (694K) -
Shiro KATO, Toshiya MORIE, Kazunori OHNO, Naoyuki YOSHIDA, Toyokichi Y ...1995 Volume 43 Issue 4 Pages 582-587
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2-Alkoxy-4-amino-N-[(4-benzyl-2-morpholinyl)methyl]-5-chlorobenzamides had been identified as the interesting members of a series of selective and potent gastroprokinetic agents. A new series of 2-amino- and 2-(substituted amino)-N-[(4-benzyl-2-morpholinyl)methyl]benzamides (13-35) has been synthesized and these compounds were examined to determine whether they have advantages over the 2-morpholinyl benzamides 1 with a 2-alkoxy group.The gastroprokinetic activity was generally reduced, but several compounds showed relatively potent activity, comparable to that of the standard agent, metoclopramide. N-[(4-Benzyl-2-morpholinyl)methyl]-4-chloro-2-[(4-chlorobenzoyl)amino]benzamide (32) showed the most potent activity in this series.View full abstractDownload PDF (921K) -
Shogo MARUI, Toshihiro YAMAMOTO, Katsuichi SUDO, Hiroshi AKIMOTO, Shoj ...1995 Volume 43 Issue 4 Pages 588-593
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe spiro-epoxy group of fumagillol (2) was selectively modified and several analogues of AGM-1470 (3) with a (dialkyl)-β-hydroxyethylsulfonium moiety were prepared. These analogues were found to inhibit angiogenesis induced by basic fibroblast growth factor in the rat micropocket assay. They also inhibited the growth of M5076 cells in vivo, but did not affect the body weight change of the tested mice during the assay.View full abstractDownload PDF (873K) -
Hiroyuki YOSHIDA, Kiyoshi IKEDA, Kazuo ACHIWA, Hiroo HOSINO1995 Volume 43 Issue 4 Pages 594-602
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVarious sulfated cerebroside analogs, which are mimicks of cerebroside, have been prepared from per-O-acetylated D-glucose, per-O-acetylated D-galactose, and per-O-acetylated D-lactose with ethyleneglycol dodecyl ether, 3-docosyloxy-1-propanol, 2-hydroxymethyl-1, 3-O-dimyristyl-1, 3-propanediol, and L-serine diamide derivatives as ceramide moieties. The synthesized sulfated glycolipids showed anti-HIV-1 activities.View full abstractDownload PDF (1446K) -
Masahiro MAKINO, Shin OHTA, Hiroshi ZENDA1995 Volume 43 Issue 4 Pages 603-606
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMinimum inhibitory concentration (the lowest concentration able to inhibit growth of microorganisms after 48 h contact) could be useful as a measure of bactericidal activity of cationic disinfectants. The relation between the minimum inhibitory concentration (μg/ml) of cationic disinfectants against gram-negative microorganisms and the adsorption tendency of these compounds onto a lipid bilayer was therefore studied using a quartz crystal microbalance (QCM) coated with synthetic multibilayer film. The adsorbed amounts of these compounds were obtained from the frequency decrease of the QCM in aqueous solutions. The calculated partition coefficients showed a good correlation with the minimum inhibitory concentrations of cationic disinfectants against E. coli and K. pneumoniae, supporting the validity of this method for predicting minimum inhibitory concentration. The results suggest that effective antibacterial agents are only slightly absorbed, and may mostly penetrate through the lipid bilayer.View full abstractDownload PDF (554K) -
Fumi NAGATSUGI, Fumiko INOUE, Shigeki SASAKI, Minoru MAEDA1995 Volume 43 Issue 4 Pages 607-615
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to understand the structural features that might lead to an in vivo radiotracer for studying cerebral fatty acid metabolism, 8-[18F]fluorooctanoate derivatives with methyl or gem-dimethyl branching at the C4 position have been prepared. 3-[18F]Fluoro- and 4-[18F]fluorooctanoic acid have also been synthesized for studying the influence of the fluorine position on the in vivo behavior of 18F-labeled octanoic acid analogs. Radiochemical synthesis was achieved by the nucleophilic displacement of a tosylate or mesylate precursor with [18F]fluoride ion. Tissue distribution studies in rats showed low cerebral uptakes of these 18F-labeled fatty acid analogs with poor brain-to-blood ratios. 3-[18F]Fluorooctanoic acid showed considerable defluorination, evident as a high bone activity level. The initial uptake of activity in the brain after injection of ethyl 8-[18F]fluoro-4-methyloctanoate and 4-[18F]-fluorooctanoic acid remained virtually unchanged over an extended time period, similar to that previously observed for the unbranched analogs, ethyl 8-[18F]fluorooctanoate and its free acid. In contrast, the 4-gem-dimethyl branched analog was rapidly and preferentially taken up by the liver. It was shown in the metabolite analysis that labeled metabolites produced from 8-[18F]fluoro-4-methyloctanoic acid were found in blood, and that the they could enter the brain to a significant degree. Thus, the present studies showed that radioactivity retention in the brain in the case of the 4-methyl branched analog was mainly attributable to its radioactive metabolites.View full abstractDownload PDF (1406K) -
Hiroyuki TAWADA, Hideaki NATSUGARI, Eiichiro ISHIKAWA, Yasuo SUGIYAMA, ...1995 Volume 43 Issue 4 Pages 616-625
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNovel 3-ureido derivatives of 4-phenylcoumarin and 4-phenyl-2-quinolone were synthesized and evaluated for acyl-CoA : cholesterol acyltransferase (ACAT)-inhibitory activity. These derivatives inhibited rat intestinal ACAT with IC50 values at the 10-8 to 10-9 M level and were found to normalize plasma cholesterol levels in cholesterol-fed rats when administered as dietary admixtures.View full abstractDownload PDF (1280K) -
Toshihide IHARA, Norio SUZUKI, Tsuneaki MAEDA, Kazuhiko SAGARA, Toshiy ...1995 Volume 43 Issue 4 Pages 626-630
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReversed micelles can be used to concentrate water-soluble materials in the water pool. In this study, the extraction of water-soluble vitamins into reversed micelles was attempted, and a flow system was used to determine the time-course of the vitamin extraction. The efficiency of extraction was strongly affected by the extraction temperature and the concentration of reversed micelles, and the selectivity depended on the size of micelles. Water-soluble vitamins could be efficiently and rapidly extracted. The selective extraction of a model mixture of vitamins from pharmaceutical preparations was also attempted. Moreover, the usefulness of the proposed method for the determination of vitamins in various commercial tablets was also demonstrated.Using of this method, the surfactant remains mixed with the extracted compounds, and so we attempted to remove the surfactant from the extract by supercritical fluid extraction. Supercritical carbon dioxide containing 7.5% ethanol as entrainer was found to be the most efficient solvent for removing residual surfactant from the extract.View full abstractDownload PDF (748K) -
Xing-Cong LI, Cong-Ren YANG, Toshihiro NOHARA, Ryoji KASAI, Kazuo YAMA ...1995 Volume 43 Issue 4 Pages 631-635
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new spirostanol glycosides, peliosanthosides A-C, were isolated from the whole plants of Peliosanthes sinica, along with two known ones. Their structures were elucidated by means of chemical and spectral evidence.View full abstractDownload PDF (761K) -
Junei KINJO, Yoshie FUJISHIMA, Kazuyo SAINO, Rui-hua TIAN, Toshihiro N ...1995 Volume 43 Issue 4 Pages 636-640
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the vines of Wisteria brachybotrys (Leguminosae), five new oleanene glycosides, called wistariasaponins YC1, 2, B3 and A2, 3, together with four known ones were isolated. Their structures have been elucidated to be 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranosyl-(1→2)-β-D-glucuronopyranosyl yunganogenin C 21-O-β-D-glucopyranoside (1), 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl yunganogenin C 21-O-β-D-glucopyranoside (2), 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranosyl-(1→2)-β-D-glucuronopyranosyl wistariasapogenol B 30-O-β-D-glucopyranoside (3), 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranosyl-(1→2)-β-D-glucuronopyranosyl wistartiasapogenol A 30-O-β-D-glucopyranoside (4) and 3-O-β-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl wistariasapogenol A 30-O-β-D-glucopyranoside (5), respectively.View full abstractDownload PDF (802K) -
Sahar EL-MEKKAWY, Meselhy R. MESELHY, Ines Tomoco KUSUMOTO, Shigetoshi ...1995 Volume 43 Issue 4 Pages 641-648
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSExtracts of 41 medicinal plants used in Egyptian folk medicine were screened for their inhibitory effects on human immunodeficiency virus-1 reverse transcriptase. The extracts of fruits of Phyllanthus emblica, Quercus pedunculata, Rumex cyprius, Terminalia bellerica, Terminalia chebula and Terminalia horrida showed significant inhibitory activity with IC50≤50 μg/ml. Through a bioassay guided-fractionation of the methanol extract of the fruit of P. emblica, putranjivain A (1) was isolated as a potent inhibitory substance with IC50=3.9 μM, together with 1, 6-di-O-galloyl-β-D-glucose (2), 1-O-galloyl-β-D-glucose (3), kaempferol-3-O-β-D-glucoside (4), quercetin-3-O-β-D-glucoside (5) and digallic acid (6). The inhibitory mode of action by 1, 2 and 6 was non-competitive with respect to the substrate but competitive with respect to a template-primer. Furthermore, the stereochemistry of 1 was established in this paper by nuclear magnetic resonance spectroscopy.View full abstractDownload PDF (1066K) -
Hiroaki KITAOKA, Chisa WADA, Reimei MOROI, Hideo HAKUSUI1995 Volume 43 Issue 4 Pages 649-653
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDifferential scanning calorimetry (DSC) curves of levofloxacin hemihydrate measured under various conditions showed different thermograms. These phenomena were attributed to be the dehydration. Dehydration caused a multiple-phase transition. Dehydration at a higher temperature (above 70°C) gave a sharp endothermic peak on the DSC curve due to the melting of the γ form, and at a lower temperature (below 50°C) gave a sharp endothermic peak due to the melting of the α form.In contrast, the thermal behavior of levofloxacin monohydrate was not affected by dehydration. The difference in the thermal behavior between the hemihydrate and the monohydrate might be attributed to a difference in the interaction between levofloxacin and crystal water. Observations by thermomicroscopy, the changes in powder X-ray diffraction patterns during heating, and single X-ray analysis all supported the above interpretation.View full abstractDownload PDF (719K) -
Tatsuro SHIRAISHI, Akimitsu SANO, Shiuji KONDO, Hiroshi YUASA, Yoshio ...1995 Volume 43 Issue 4 Pages 654-659
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn the process of granulation for tableting using theophylline as a model drug, the power consumption pattern and the physical properties of the granules were examined with varied particle sizes of theophylline. During kneading of the physical mixtures containing these varied particle sizes into granules for tableting, the first peak of the power consumption curve declined with decreasing particle size of the physical mixtures and a second peak appeared for physical mixtures with smaller particle sizes. The optimal kneading end point for granules was at the end of the first peak for mixtures with larger particles and at the beginning of the second peak for those with smaller particles.The best granules for tableting prepared from individual physical mixtures at different end points had maximum pore volume and consisted of a mixture of similar size of porous loose agglomerates and bulk powder as reported previously. This inner structure of granules is assumed to induce plastic deformation and particle movement upon compression and to result in high mechanical tablet strength.View full abstractDownload PDF (1411K) -
Tetsuya OZEKI, Hiroshi YUASA, Yoshio KANAYA, Katsutoshi OISHI1995 Volume 43 Issue 4 Pages 660-665
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSolid dispersion films were prepared with a highly water-soluble medicine (oxprenolol hydrochloride (OXP)), four grades of water-insoluble ethylcellulose (EC) having different molecular weights and water-soluble hydroxypropyl cellulose (HPC). The internal structure of the solid dispersion films and the penetration of the dissolution medium into the films were studied to clarify the mechanism of OXP release from the OXP-EC and OXP-EC-HPC solid dispersion systems having various molecular weights of EC.In the OXP-EC system, the release rate of OXP slightly decreased with increasing molecular weight of EC and the mechanism of OXP release was hardly affected by the molecular weight of EC. In the OXP-EC-HPC system, the release rate of OXP markedly decreased with increasing molecular weight of EC. When EC with the lowest molecular weight of the four grades was used, the same mechanism of OXP release was observed as in the OXP-EC system, but it was clear that OXP was released from the films with the two higher-molecular-weight grades of EC through a diffusion-controlled release mechanism. This result can be explained in terms of diffusion of OXP through the quasi-equilibrium swollen gel region formed by rapid hydration of HPC with water penetrating into the solid dispersion film.View full abstractDownload PDF (1223K) -
Kunikazu MORIBE, Etsuo YONEMOCHI, Toshio OGUCHI, Yoshinobu NAKAI, Keij ...1995 Volume 43 Issue 4 Pages 666-670
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe infrared (IR) peak shift in benzoic acid-additive mixtures has been studied. Benzoic acid crystals, in which benzoic acid molecules form a stable dimeric structure, showed the carbonyl stretching (vC=O) band at 1688 cm-1.The vC=O band of benzoic acid was shifted to a higher wavenumber of 1720 cm-1 when IR measurement was carried out for a physical mixture of benzoic acid with heptakis-(2, 6-di-O-methyl)-β-cyclodextrin (DMβCD) by KBr compression method. The shifted peak reverted to the original position when measured again by Nujol method following pulverization of the KBr disk. These phenomena were observed only in the case of using methylated polysaccharides as additives. The results of X-ray diffraction and solid-state 13C-NMR spectroscopy indicated that the crystal structure of benzoic acid was not influenced by compression and the dimeric structure was maintained.From the results of IR spectra using deuterated benzoic acid, the peculiar phenomena could be explained in terms of the changes in the hydrogen bonding feature of benzoic acid in the compressed disk with DMβCD.View full abstractDownload PDF (697K) -
Eihei FUKUOKA, Katsuhide TERADA, Midori MAKITA, Shigeo YAMAMURA1995 Volume 43 Issue 4 Pages 671-676
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe lattice distortion and size of crystallites along a particular lattice direction in solid pharmaceuticals were determined by profile analysis using a peak profile of X-ray powder diffraction. The analysis was carried out according to either the paracrystal or micro strain model. After correction for instrumental broadening, pure diffraction profiles of several orders of 0k0 reflections for dibasic calcium phosphate dihydrate (DCPD) and those of 0kk reflections for griseofulvin (GRIS) were obtained. Then, the integral breadths of the pure diffraction profiles were calculated.Lattice distortion and the size of crystallites along [0k0] of DCPD and those along [0kk] of GRIS were determined from the slope and ordinate intercept of the straight line obtained by plotting the integral breadth against the order of reflection according to the theory of paracrystalline diffraction. DCPD powders were characterized to have paracrystalline lattice distortion, in which broadening profiles of both the size of crystallites and lattice distortion are of a Gaussian shape. The lattice distortion along [0k0] increased, while the size of crystallites scarcely decreased with the progress of grinding time. GRIS powders were characterized to have paracrystalline lattice distortion, in which both broadening profiles of the size of crystallites and lattice distortion, are of a Cauchy (Lorentzian) shape.The lattice distortion along [0kk] increased and the size of crystallites decreased with the progress of grinding time.The effects of lattice distortion on physicochemical and pharmaceutical properties of DCPD and GRIS powders were discussed.View full abstractDownload PDF (849K) -
Hideko INOUE, Yoshinobu BABA, Mitsutomo TSUHAKO1995 Volume 43 Issue 4 Pages 677-678
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe phosphorylation of cellulose with inorganic cyclo-triphosphate (P3m) was studied in aqueous solutions under various conditions. One glucose unit per thirty glucose units of cellulose molecule was phosphorylated under the optimum conditions (25% P3m, pH 12, and 50°C). Phosphorylated cellulose is characterized by its adsorption of metal ions and noncombustibility.View full abstractDownload PDF (442K) -
Ken-ichi IWAMOTO, Sumiko SUZUKI, Etsuo OISHI, Ken-ichi TANJI, Akira MI ...1995 Volume 43 Issue 4 Pages 679-682
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn the reaction of 1-substituted phthalazines with ynamines, there are three patterns of ring transformation, giving naphthalene derivatives through addition-cyclization-denitrogenation (type A), giving benzodiazocine derivatives through addition-cyclization-ring expansion (type B), and giving penta-substituted pyridine derivatives through N-N bond cleavage of the pyridazine ring (type C). In these reactions, it is considered that the substituent group at the 1-position of the phthalazine ring is a significant factor determining the outcome.View full abstractDownload PDF (597K) -
Atsunori SANO, Masami ISHIHARA, Jun YOSHIHARA, Motoshige SUMINO, Hirom ...1995 Volume 43 Issue 4 Pages 683-685
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA facile and practical synthesis of 9-methyl-3-(1H-tetrazol-5-yl)-4H-pyrido[1, 2-α]pyrimidin-4-one (4), the potassium salt of which is used clinically as an anti-asthma agent, is described. Treatment of a key intermediate (6b), prepared from 2-amino-3-methylpyridine (1) and 2-ethoxymethylene-1, 3-propanedinitrile, with sodium azide in N, N-dimethylformamide gave predominantly the cyanotetrazole (7a), while in acetic acid it gave exclusively the iminotetrazole (7b), which was easily converted into 4 by acid hydrolysis. A one-pot process starting from 6b to give 4, avoiding the use of explosive aluminum azide, was established.View full abstractDownload PDF (574K) -
Yukio MASAKI, Tsuyoshi MIURA, Isao MUKAI, Ikuhiro IWATA, Hirohisa ODA, ...1995 Volume 43 Issue 4 Pages 686-688
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA reagent combination system, tetracyanoethylene-30% hydrogen peroxide, was found to epoxidize olefins efficiently in acetonitrile at room temperature in a stereospecific manner with retention of the configuration of the double bond.View full abstractDownload PDF (554K) -
Yutaka TAKEUCHI, Makoto SUNAGAWA, Yutaka ISOBE, Yukari HAMAZUME, Tetsu ...1995 Volume 43 Issue 4 Pages 689-692
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe stability and the degradation products of 1β-methylcarbapenem, meropenem in aqueous solution were investigated. In pH 4-8 dilute solution pseudo-first-order degradation was observed, and good stability of meropenem in aqueous solution was demonstrated by the effect of 1β-methyl group against hydrolysis of β-lactam ring. As degradation products, the β-lactam hydrolyzed product and the dimer product resulting from intermolecular aminolysis of β-lactam ring by the amine of the second molecule were described.View full abstractDownload PDF (570K) -
Minoru UCHIDA, Kenji OTSUBO, Jun MATSUBARA, Tadaaki OHTANI, Seiji MORI ...1995 Volume 43 Issue 4 Pages 693-698
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn a search for inhibitors of gastric H+/K+ATPase, 4-(phenylamino)quinoline-3-carboxamides were synthesized and evaluated for antisecretory activity against histamine-induced gastric acid secretion in rats. These compounds were synthesized by condensation of aniline derivatives with N-substituted 4-chloroquinoline-3-carboxamides, which were obtained from treatment of 4(1H)-quinolinone-3-carboxylic acid with thionyl chloride. Most of the compounds inhibited histamine-induced gastric acid secretion in rats. Among them, N-allyl-4-(2-ethylphenylamino)quinoline-3-carboxamide (4h) was the most potent inhibitor and had the best profile as a candidate antiulcer agent. This compound showed reversible, K+-competitive gastric H+/K+-ATPase inhibitory activity.View full abstractDownload PDF (879K) -
Shiro KATO, Toshiya MORIE, Naoyuki YOSHIDA1995 Volume 43 Issue 4 Pages 699-702
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to confirm the proposed structures of two metabolites 3 and 4 of the gastroprokinetic agent mosapride [4-amino-5-chloro-2-ethoxy-N-{[4-(4-fluorobenzyl)-2-morpholinyl]methyl}benzamide, 2], the compounds were synthesized and their biological activity was examined. The structures of the metabolites were confirmed by means of comparison with the synthetic compounds. The serotonin 5-HT4 receptor agonistic activities of the metabolites were found to be less than that of mosapride.View full abstractDownload PDF (714K) -
Pengyue SUN, Wen YE, Jifu ZHAO, Yuping PEI, Zhixue WANG, Yingjie CHEN, ...1995 Volume 43 Issue 4 Pages 703-704
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new flavonol glycoside, epimedoside (1), was isolated together with three known compounds, identified as icariside A1 (2), maltol (3) and salidroside (4), from the aerial parts of Epimedium koreanum NAKAI (Berberidaceae).Their structures were established by spectroscopic methods and chemical evidence.View full abstractDownload PDF (490K) -
Akihiro OHTA, Fumiaki OKAZAKI, Yoshiko YAMANOI, Mikiko MAEDA, Yutaka A ...1995 Volume 43 Issue 4 Pages 705-707
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of 2-(methylthio)-3, 6-dihydro-3, 5-dimethyl-6-oxo-1-aryl- and alkyl-1-pyrimidinium-4-olates (1a-d) with alkenes carrying electron withdrawing groups gave 1, 4-cycloadducts in good yields, demonstrating that 1, 4-dipolar cycloaddition reaction proceeds with regio- and diastereoselectivity.View full abstractDownload PDF (381K) -
Masayuki YAMASHITA, Kazunori OKUYAMA, Takashi OHHARA, Ikuo KAWASAKI, S ...1995 Volume 43 Issue 4 Pages 708-710
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCyclopropane ring of 2- and 2, 3-substituted cyclopropanecarboxylates (1) was regioselectively cleaved using SmI2-HMPA-THF system in the presence of tert-BuOH to give 4- and 3, 4-substituted butyrates (2) in moderate to good yields.View full abstractDownload PDF (443K) -
Kazuyuki MIYASHITA, Masahiro NISHIMOTO, Tetsuya ISHINO, Satoshi OBIKA, ...1995 Volume 43 Issue 4 Pages 711-713
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBoth C-4 stereoisomers of novel Hantzch-type 4-aryl- and 4-methyl-1, 4-dihydropyridines 3 having a p-tolylsulfinyl group at C-5 were efficiently synthesized in optically pure forms starting from the α-sulfinyl enones 6 which could be easily obtained from (-)-menthyl (S)-p-tolylsulfinate (4). The stereochemistry at C-4 was found to be largely responsible for the biological activities as calcium channel antagonists of these compounds.View full abstractDownload PDF (467K) -
Masao TOYOTA, Hiroki KOYAMA, Toshihiro HASHIMOTO, Yoshinori ASAKAWA1995 Volume 43 Issue 4 Pages 714-716
Published: April 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA sesquiterpene alcohol with a new rearranged pinguisane carbon skeleton, which is named a neo-pinguisane type, has been isolated from the ether extract of the liverwort Dicranolejeunea yoshinagana (Hatt.) Mizut., together with two new pinguisane-type sesquiterpenoids and previously known deoxopinguisone and ptychanolide. Their structures were established by spectroscopic means.View full abstractDownload PDF (461K)
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