Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
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ISSN-L : 0009-2363
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Volume 50, Issue 11
Displaying 1-25 of 25 articles from this issue
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Regular Articles
  • New Cholinesterase Inhibiting Steroidal Alkaloids from the Leaves of Sarcococca coriacea of Nepalese Origin
    Surya K. Kalauni, Muhammad Iqbal Choudhary, Asaad Khalid, Mangala Devi ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 11 Pages 1423-1426
    Published: 2002
    Released on J-STAGE: November 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1423
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    From the leaves of Sarcococca coriacea two new steroidal alkaloids, epoxynepapakistamine-A [(20S)-20-(N-methylamino)-3β-(tigloylamino)-5α-pregna-16α,17α-epoxy-2β,4β-di-O-acetate] (1), and epoxysarcovagenine-D [(20S)-20-(N-methylamino)-3β-(tigloylamino)-5α-pregna-2-en-16α,17α-epoxy-4-one] (2), and two known compounds funtumafrine C [(20S)-20-(N,N-dimethylamino)-5α-pregna-3-one] (3) and N-methylfuntumine (4) were isolated. Their structures were elucidated on the basis of their spectral properties. The compounds 1, 3 and 4 were found to have cholinesterase inhibitory activity when tested for the inhibition of electric eel acetylcholinesterase and horse serum butyrylcholinesterase. They inhibited both enzymes in a concentration dependent fashion.
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  • Microbial Transformation of Rubijervine
    Khalid A. El Sayed, D. Chuck Dunbar
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 11 Pages 1427-1429
    Published: 2002
    Released on J-STAGE: November 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1427
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    Preparative-scale fermentation of rubijervine (1), the known 22,26-epiminocholestane Veratrum alkaloid, with Cunninghamella echinulata ATCC 9244 has resulted in the isolation of the new metabolites 7α-hydroxyrubijervine (2) and solanid-5-ene-3β,12α-diol-1-one (3). Structure elucidation of these metabolites was based primarily on 1D- and 2D-NMR analyses. The microbe C. echinulata ATCC 9244 was able to metabolize rings A and B of rubijervine but failed to metabolize rings C, D or its N-containing side chain, a finding which is analogous to the results of previous fermentation studies of steroidal alkaloids.
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  • Determination of Optimum Processing Temperature for Transformation of Glyceryl Monostearate
    Toshio Yajima, Shigeru Itai, Hirofumi Takeuchi, Yoshiaki Kawashima
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 11 Pages 1430-1433
    Published: 2002
    Released on J-STAGE: November 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1430
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    The purpose of this study was to clarify the mechanism of transformation from α-form to β-form via β′-form of glyceryl monostearate (GM) and to determine the optimum conditions of heat-treatment for physically stabilizing GM in a pharmaceutical formulation. Thermal analysis repeated twice using a differential scanning calorimeter (DSC) were performed on mixtures of two crystal forms. In the first run (enthalpy of melting: ΔH1), two endothermic peaks of α-form and β-form were observed. However, in the second run (enthalpy of melting: ΔH2), only the endothermic peak of the α-form was observed. From a strong correlation observed between the β-form content in the mixture of α-form and β-form and the enthalpy change, (ΔH1−ΔH2)/ΔH2, β-form content was expressed as a function of the enthalpy change. Using this relation, the stable β-form content during the heat-treatment could be determined, and the maximum β-form content was obtained when the heat-treatment was carried out at 50 °C. An inflection point existed in the time course of transformation of α-form to β-form. It was assumed that almost all of α-form transformed to β′-form at this point, and that subsequently only transformation from β′-form to β-form occurred. Based on this aspect, the transformation rate equations were derived as consecutive reaction. Experimental data coincided well with the theoretical curve. In conclusion, GM was transformed in the consecutive reaction, and 50 °C was the optimum heat-treatment temperature for transforming GM from the α-form to the stable β-form.
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  • Synthesis of Water-Soluble Polymeric Prodrugs Possessing 4-Methylcatechol Derivatives by Mechanochemical Solid-State Copolymerization and Nature of Drug Release
    Shin-ichi Kondo, Yasushi Sasai, Masayuki Kuzuya, Shoei Furukawa
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 11 Pages 1434-1438
    Published: 2002
    Released on J-STAGE: November 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1434
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    In this study we synthesized the water-soluble polymeric prodrugs possessing a 4-methylcatechol (4MC) derivative as a side chain by mechanochemical solid-state copolymerization. 1-Benzoyl-4-methylcatechol (Bz4MC) was selected as a model compound of 4MC, and its methacryloyl derivative (1) was synthesized. 6-O-Methacryloyl-D-galactose (2) was also prepared as a water-soluble monomer. The mechanochemical solid-state copolymerization of 1 and 2 was carried out to obtain the water-soluble polymeric prodrug possessing the Bz4MC as a side chain. The mechanochemical copolymerization of 1 and 2 proceeded to completion, and the polymeric prodrug produced possessed a narrow molecular weight distribution. Three kinds of polymeric prodrugs, whose compositions were different from one another, were hydrolyzed in vitro. The hydrolysis of these polymeric prodrugs proceeded to completion. The rate constants of hydrolysis decreased with increasing the mole fraction of 1 in polymeric prodrug. It was suggested that the rate constant of hydrolysis could be controlled by the composition, the mole fraction of 1 in the polymeric prodrug.
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  • Analysis of the Release Process of Phenylpropanolamine Hydrochloride from Ethylcellulose Matrix Granules
    Atsuko Fukui, Ryuta Fujii, Yorinobu Yonezawa, Hisakazu Sunada
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 11 Pages 1439-1442
    Published: 2002
    Released on J-STAGE: November 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1439
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    The release properties of phenylpropanolamine hydrochloride (PPA) from ethylcellulose (EC, ethylcellulose 10 cps (EC#10) and/or 100 cps (EC#100)) matrix granules prepared by the extrusion granulation method were examined. The release process could be divided into two parts, and was well analyzed by applying square-root time law and cube root law equations, respectively. The validity of the treatments was confirmed by the fitness of the simulation curve with the measured curve. At the initial stage, PPA was released from the gel layer of swollen EC in the matrix granules. At the second stage, the drug existing below the gel layer dissolved, and was released through the gel layer. Also, the time and release ratio at the connection point of the simulation curves was examined to determine the validity of the analysis. Comparing the release properties of PPA from the two types of EC matrix granules, EC#100 showed more effective sustained release than EC#10. On the other hand, changes in the release property of the EC#10 matrix granule were relatively more clear than that of the EC#100 matrix granule. Thus, it was supposed that EC#10 is more available for controlled and sustained release formulations than EC#100.
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  • β-N-Cyanoethyl Acyl Hydrazide Derivatives: A New Class of β-Glucuronidase Inhibitors
    Khalid Mohammed Khan, Shahida Shujaat, Shagufta Rahat, Safdar Hayat, ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 11 Pages 1443-1446
    Published: 2002
    Released on J-STAGE: November 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1443
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    Eight new β-N-substituted acyl hydrazides along with their corresponding acyl derivatives were synthesized and screened for in vitro β-glucuronidase inhibition and found to be active against the enzyme. All of these compounds were found to be noncompetitive inhibitors except for N′-(2-cyanoethyl)-4-hydroxy benzohydrazide (10), which was found to be an uncompetitive inhibitor. Structure–activity relationship studies indicated that the benzyloxy group present in compounds 12 and 13 is responsible for the β-glucuronidase inhibition activity.
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  • 5α-Reductase Inhibitory and Antiandrogenic Activities of Novel Steroids in Hamster Seminal Vesicles
    Marisa Cabeza, Eugene Bratoeff, Eugenio Flores, Elena Ramírez, ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 11 Pages 1447-1452
    Published: 2002
    Released on J-STAGE: November 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1447
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    The pharmacological activity of several 16-bromosubstituted trienediones 4 and 5, 16-methyl substituted dienediones 6 and 7 and the 16-methyl substituted trienedione 8 was determined on gonadectomized hamster seminal vesicles by measuring the in vitro conversion of testosterone (T) to dihydrotestosterone (DHT) as 5α-reductase inhibitors and also the ability of these steroids to bind to the androgen receptor. Steroids 6 and 7 when injected together with T decreased the weight of the seminal vesicles thus showing an antiandrogenic effect. Compounds 5 and 6 reduced substantially the conversion of T to DHT and therefore can be considered good inhibitors for the enzyme 5α-reductase; however both steroids failed to form a complex with the androgen receptor. On the other hand compound 7 which showed a very small inhibitory activity for the enzyme 5α-reductase, exhibited a very high affinity for the androgen receptor and thus can be considered an effective antiandrogen. This compound also reduced substantially the weight of the seminal vesicles. Steroids 4 and 8 did not reduce the weight of the seminal vesicles and exhibited a low affinity for the androgen receptor; 8 showed a weak 5α-reductase inhibitory activity, whereas 4 exhibited a weak androgenic effect.
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  • Phosphorylation of Disaccharides with Inorganic cyclo-Triphosphate in Aqueous Solution
    Hideko Inoue, Naoto Tone, Hirokazu Nakayama, Mitsutomo Tsuhako
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 11 Pages 1453-1459
    Published: 2002
    Released on J-STAGE: November 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1453
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    The phosphorylation of disaccharides by inorganic cyclo-triphosphate (P3m) with a six-membered ring was examined in aqueous solution. In the phosphorylation of cellobiose, lactose, and α,α-trehalose with P3m, β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl 1-triphosphate, β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl 1-triphosphate, and 3-O-triphospho-α-D-glucopyranosyl-(1→1)-α-D-glucopyranoside were synthesized with maximum yields of 28%, 35%, and 20%, respectively. In the reactions of maltose and sucrose with P3m, two phosphorylated products were obtained in yields of 42% and 58%, respectively. The main phosphorylated products were assigned to α-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl 1-triphosphate and β-D-fructofuranosyl-(2→1)-2-O-triphospho-α-D-glucopyranoside by heteronuclear multiple bond correlation (HMBC) NMR. The phosphorylation mechanism of disaccharides with P3m is discussed.
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  • Water-Soluble Constituents of Anise: New Glucosides of Anethole Glycol and Its Related Compounds
    Toru Ishikawa, Eiko Fujimatu, Junichi Kitajima
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 11 Pages 1460-1466
    Published: 2002
    Released on J-STAGE: November 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1460
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    From the water-soluble portion of the methanolic extract of the fruit of anise (Pimpinella anisum L.), which has been used as a spice and medicine since antiquity, twelve new and five known glucosides of phenylpropanoids, including four stereoisomers of anethole glycol 2′-O-β-D-glucopyranoside and four stereoisomers of 1′-(4-hydroxyphenyl)propane-1′,2′-diol 2′-O-β-D-glucopyranoside were isolated together with anethole glycols and guaiacyl glycerol. The structures of the new compounds were clarified by spectral investigation.
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  • Constituents of Holothuroidea, 12. Isolation and Structure of Glucocerebrosides from the Sea Cucumber Holothuria pervicax
    Koji Yamada, Kaori Sasaki, Yasuo Harada, Ryuichi Isobe, Ryuichi Higuch ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 11 Pages 1467-1470
    Published: 2002
    Released on J-STAGE: November 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1467
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    Ten glucocerebrosides, HPC-3-A—HPC-3-J, have been isolated from their obtained parent glucocerebroside molecular species HPC-3, together with other glucocerebroside molecular species HPC-1 and HPC-2, from the less polar lipid fraction of a chloroform/methanol extract of the sea cucumber Holothuria pervicax. The structures of these glucocerebrosides have been determined on the basis of chemical and spectroscopic evidence. Reversed-phase HPLC, including a recycling system, was effective in isolating these glucocerebrosides, revealing a very close resemblance in structure, though the problem due to regio-isomers remains.
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  • Water-Soluble Constituents of Cumin: Monoterpenoid Glucosides
    Toru Ishikawa, Tomomi Takayanagi, Junichi Kitajima
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 11 Pages 1471-1478
    Published: 2002
    Released on J-STAGE: November 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1471
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    From the water-soluble portion of the methanol extract of cumin (fruit of Cuminum cyminum L.), which has been used as a spice and medicine since antiquity, sixteen monoterpenoid glucosides, including twelve new compounds, were isolated. Their structures were clarified by spectral investigation.
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  • 1,5-Dimethyl-6H-pyridazino[4,5-b]carbazole, a 3-Aza Bioisoster of the Antitumor Alkaloid Olivacine
    Norbert Haider, Eddy Sotelo
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 11 Pages 1479-1483
    Published: 2002
    Released on J-STAGE: November 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1479
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    A series of b-fused carbazoles structurally related to pyrido[4,3-b]carbazole-type alkaloids was prepared, utilizing the Diels–Alder reaction of 1-methylpyrano[3,4-b]indol-3(9H)-one with electron-deficient acetylenic dienophiles as the key step. The title compound (14) thus obtained in only four steps represents a new 3-aza analog of the antitumor natural product, olivacine.
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  • Ardisiphenols and Other Antioxidant Principles from the Fruits of Ardisia colorata
    Megumi Sumino, Toshikazu Sekine, Nijsiri Ruangrungsi, Kazuei Igarashi, ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 11 Pages 1484-1487
    Published: 2002
    Released on J-STAGE: November 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1484
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    Novel alkylphenols, ardisiphenols A—C (1—3) and a novel bergenin derivative, demethoxybergenin (10) were isolated from the fruits of Ardisia colorata (Myrsinaceae), together with known alkylresorcinols (4—6), embelin (7), myricetin (8), quercetin (9), bergenin (11), norbergenin (12), kaempferol (13), quercetin-3-O-β-D-glucopyranoside (14) and gallic acid (15). Their structures were determined by NMR, MS(/MS) analyses and other spectroscopic methods. Ardisiphenols showed moderate scavenging activities toward 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals and showed cytotoxicity against the murine breast cancer cell line, FM3A.
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Notes
  • Two New Rearranged Taxoids from Taxus wallichiana ZUCC.
    Muhammad Iqbal Choudhary, Abdul Majeed Khan, Habib-ur-Rehman, Atta-u ...
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 11 Pages 1488-1490
    Published: 2002
    Released on J-STAGE: November 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1488
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    Two new rearranged taxane diterpenoids, 5α,7β,10β,13α-tetrahydroxy-2α,9α,15-triacetoxy-11(15→1)-abeo-taxa-4(20), 11-diene (1) and 5α,9α,10β,13α-tetraacetoxy-15-hydroxy-11(15→1)-abeo-taxa-4(20), 11-diene (2) have been isolated from the barks of Taxus wallichiana. The structures of these compounds have been confirmed by modern spectroscopic techniques.
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  • Synthesis of Symmetrical 1,5-bis-thio-Substituted Anthraquinones for Cytotoxicity in Cultured Tumor Cells and Lipid Peroxidation
    Hsu-Shan Huang, Jeng-Fong Chiou, Hui-Fen Chiu, Jing-Min Hwang, Pen-Yua ...
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 11 Pages 1491-1494
    Published: 2002
    Released on J-STAGE: November 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1491
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    The synthesis of a series of anthraquinone moieties bearing symmetrical sulfur-linked substituents in the 1 and 5 positions is described. These compounds were evaluated for their ability to inhibit the growth of suspended rat glioma C6 cells and human hepatoma G2 cells, respectively. In addition, the redox property of the compounds was determined based on the inhibition of lipid peroxidation in model membranes. Compounds 2a and 2h in this series compared favorably and exhibited the most potent cytotoxicity (0.02, 0.05 μM) against C6 cells in the XTT colorimetric assay. As far as redox properties are concerned, all bis-thio-anthraquinones show potential lipid peroxidation in model membranes very close to that of mitoxantrone (MX), and 2a, 2d, 2e, 2i, 2j, and 2k have more potential than that of MX. The lack of cytotoxicity of compound 2i cannot be related to lipid peroxidation, but the steric and electronic properties of the side-chain substituent maybe impair effective recognition of the cleavable complex. In contrast to MX, 2a and 2h are cytotoxic in rat glioma C6 cells and do not enhance lipid peroxidation in model membranes.
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  • Eudragit NE30D Based Metformin/Gliclazide Extended Release Tablets: Formulation, Characterisation and in Vitro Release Studies
    Enose Appavoo Arno, Prithiviraj Anand, Kesavan Bhaskar, Somasundaram R ...
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 11 Pages 1495-1498
    Published: 2002
    Released on J-STAGE: November 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1495
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    Metformin/Gliclazide extended release tablets were formulated with Eudragit NE30D by wet granulation technique. Two batches were prepared in order to study influence of drug polymer ratio on the tablet formation and in vitro drug release. The formulated tablets were characterized by disintegration time, hardness, friability, thickness, weight variation, and in vitro drug release. The percentage of polymer, with respect to Metformin/Gliclazide, required to produce tablets with acceptable qualities was 9 to 13.45. The percentage of polymer below this range released the drug immediately and above this range produced granules not suitable for tablet formation. The quantity of Metformin/Gliclazide present in the tablets and the release medium were estimated by a validated HPLC method. The formulated tablets had acceptable physicochemical characters and released the drug over 6—8 h. The data obtained from in vitro release studies were fitted with various kinetic models and was found to follow Higuchi kinetics.
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  • Cytotoxic Compounds from Polygala vulgaris
    Stefano Dall'Acqua, Gabbriella Innocenti, Giampietro Viola, Anna Piova ...
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 11 Pages 1499-1501
    Published: 2002
    Released on J-STAGE: November 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1499
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    To search for antitumor agents from plants, we studied Polygala vulgaris since cytotoxic lignans are known to occur in some Polygala species. Preliminary data on plant petrol ether, chloroform, and methanol extracts from the roots and aerial parts, showed in vitro cytotoxic activity against the solid tumor LoVo cell line. Fractionation of the active extracts led to the isolation of three new compounds, a derivative of aucuparine and two xanthones, as well as a known methylsinapate. All compounds were tested for in vitro cytotoxic activity using two cell lines, LoVo and its strain, which express resistance to common antitumor agents.
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  • Ab Initio Molecular Orbital Study of the Reactivity of Active Alkyl Groups. V. Nitrosation Mechanism of Acetone with syn-Form of Methyl Nitrite
    Tokihiro Niiya, Hirohito Ikeda, Miho Yukawa, Yoshinobu Goto
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 11 Pages 1502-1506
    Published: 2002
    Released on J-STAGE: November 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1502
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    The mechanisms of nitrosation of acetone through sodium enolate [CH3CO1CH2]−Na+ (1) or naked enolate [CH3CO1CH2]− (2) with methyl nitrite CH3O3NO2 (3), and the reactivity of the syn-form of 3 (syn-3) during the C–N bond formation process were investigated using ab initio molecular orbital (MO) methods. Our results have demonstrated the predominant formation of E-1-hydroxyimino-2-oxo-propane CH3COCH=NOH (4E) when the complex [CH3CO1CH2NO2(O3CH3)]−Na+ was produced kinetically via a metal-chelated pericyclic transition state (TSCHELATED), in which the O3 atom of syn-3 was coordinated to the Na+ atom of 1.
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  • Constituents with Radical Scavenging Effect from Opuntia dillenii: Structures of New α-Pyrones and Flavonol Glycoside
    Yingkun Qiu, Yingjie Chen, Yupin Pei, Hisashi Matsuda, Masayuki Yoshik ...
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 11 Pages 1507-1510
    Published: 2002
    Released on J-STAGE: November 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1507
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    The aqueous ethanolic extract from the fresh stems of Opuntia dillenii HAW. showed potent radical scanvenging activity. Three new compounds, opuntioside I, 4-ethoxyl-6-hydroxymethyl-α-pyrone, and kaempferol 7-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside, were isolated from the extract. The structures of the new compounds were determined on the basis of chemical and physicochemical evidence and the radical scavenging effects of principal constituents were examined.
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  • The Improved Synthesis of OPC-29030, a Platelet Adhesion Inhibitor via Diastereoselective Oxidation of Chiral Non-racemic Sulfide
    Masato Matsugi, Rieko Shimada, Shinji Ohata, Masatomo Nojima, Norio Fu ...
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 11 Pages 1511-1513
    Published: 2002
    Released on J-STAGE: November 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1511
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    An improved synthetic route of OPC-29030, the platelet adhesion inhibitor, was established via the diastereoselective oxidation of a chiral non-racemic sulfide (R)-5 to (SS)-6 by the catalytic oxidation using VO(acac)2 and cumene hydroperoxide (CHP) in the presence of MS4A. Under the current condition, the diastereoselectivity was not influenced by the presence of moisture, and moderate to high selectivity (72% de) was obtained at −30 °C. The obtained sulfoxide, which diastereomeric excess was easily raised by the recrystallization, could successfully lead to OPC-29030.
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  • Trypanocidal Terpenoids from Laurus nobilis L.
    Nahoko Uchiyama, Keiji Matsunaga, Fumiyuki Kiuchi, Gisho Honda, Akiko ...
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 11 Pages 1514-1516
    Published: 2002
    Released on J-STAGE: November 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1514
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    Trypanocidal constituents of dried leaves of Laurus nobilis L. (Lauraceae) were examined. Activity-guided fractionation of the methanol extract resulted in the isolation of two guaianolides, dehydrocostus lactone (1) and zaluzanin D (2), and a new p-menthane hydroperoxide, (1R,4S)-1-hydroperoxy-p-menth-2-en-8-ol acetate (3). The minimum lethal concentrations of these compounds against epimastigotes of Trypanosoma cruzi were 6.3, 2.5, and 1.4 μM, respectively.
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  • Novel and Efficient Synthesis of 4-Dimethylamino-2-glycosylaminoquinazolines by Cyclodesulfurization of Glycosyl Thioureas with Dimethylcyanamide
    Yasuo Gama, Isao Shibuya, Masao Shimizu
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 11 Pages 1517-1519
    Published: 2002
    Released on J-STAGE: November 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1517
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    4-Dimethylamino-2-glycosylaminoquinazoline derivatives were synthesized by cyclodesulfurization of N-aryl-N′-glycosyl thioureas with dimethylcyanamide in the presence of silver triflate in good yields.
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  • A Novel Push–Pull Diels–Alder Diene: Reactions of 4-Alkoxy- or 4-Phenylsulfenyl-5-chalcogene-substituted 1-Phenylpenta-2,4-dien-1-one with Electron-Deficient Dienophiles
    Mitsuhiro Yoshimatsu, Masaru Hibino, Masaru Ishida, Genzoh Tanabe, Osa ...
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 11 Pages 1520-1524
    Published: 2002
    Released on J-STAGE: November 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1520
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    5-(Phenylselenenyl)- and 5-(phenylsulfenyl)-4-ethoxy-1-phenyl-2,4-pentadien-1-ones (2) and (3) underwent [4+2] cycloaddition with N-methyl and N-phenylmaleimides and successive isomerization to give the 7-benzoyl-3a,4,5,7a-tetrahydro-1H-isoindole-1,3(2H)-diones 5, 8 and 9 in good yields. The 4-ethoxy group on the 2,4-pentadien-1-one was found to be effective to facilitate the cycloaddition with dienophiles. We also performed other [4+2] cycloadditions of 2,4-pentadien-1-ones with DMAD or naphthoquinone.
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  • Cascade Reaction of Imines with Phenylsulfinylallene. X-Ray Structure of the Product and Its Formation Mechanism
    Shigeru Oiso, Yasuyuki Yoshitake, Masashi Eto, Kazunobu Harano
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 11 Pages 1525-1527
    Published: 2002
    Released on J-STAGE: November 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1525
    JOURNAL FREE ACCESS
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    The structure of the product derived from the reaction of a dihydropyridine derivative with phenylsulfinylallene has been clarified by a single crystal X-ray analysis and the formation mechanism is discussed on the basis of the reaction-path calculations by semiempirical and ab initio molecular orbital methods.
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