Novel deoxy-selenylconduritols: chemoenzymatic synthesis and biological evaluation

被引:10
|
作者
Bellomo, Ana [1 ]
Bertucci, Ana [2 ]
Stefani, Helio [3 ,4 ]
Vazquez, Alvaro [2 ]
Gonzalez, David [1 ]
机构
[1] Univ Republica, UdelaR, Fac Quim, Lab Sintesis Organ, Montevideo, Uruguay
[2] Univ Republica, UdelaR, Fac Quim, Lab Farmacognosia & Prod Nat, Montevideo, Uruguay
[3] Univ Sao Paulo, Fac Ciencias Farmaceut, Dept Farm, Sao Paulo, Brazil
[4] Univ Fed Sao Paulo, Dept Biofis, Sao Paulo, Brazil
基金
巴西圣保罗研究基金会;
关键词
EFFICIENT SYNTHESIS; (-)-CONDURITOL C; CONDURITOL; CYCLITOLS; SELENIUM; CONDURAMINE; DERIVATIVES; HYDROLYSIS; EPOXIDES; ANALOGS;
D O I
10.1016/j.tetasy.2009.11.004
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The first synthesis of two selenyldeoxycyclitols (4-bromo-2-phenylselenyl conduritol F and 6-phenylselenylconduritol F) is reported via a chemoenzymatic enantioselective route. The key step of the synthesis is the selenolysis of a vinyl epoxide. The new compounds were evaluated for their capacity to inhibit the growth of different microorganisms using a modification of the agar diffusion technique with thin layer chromatography plates as support. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2673 / 2676
页数:4
相关论文
共 50 条
  • [1] CYTOTOXIC EPOXYSTEROLS: CHEMOENZYMATIC SYNTHESIS, BIOLOGICAL EVALUATION AND SAR
    Carvalho, Joao F. S.
    Cruz Silva, M. Manuel
    Moreira, Joao N.
    Simoes, Sergio
    Sa e Melo, M. Luisa
    DRUGS OF THE FUTURE, 2009, 34 : 97 - 97
  • [2] Synthesis and biological evaluation of novel 2′-deoxy-4′-thioimidazole nucleosides
    Wang, Y
    Inguaggiato, G
    Jasamai, M
    Shah, M
    Hughes, D
    Slater, M
    Simons, C
    BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (03) : 481 - 487
  • [3] Chemoenzymatic synthesis and biological evaluation of (-)-conduramine C-4
    Bellomo, Ana
    Giacomini, Cecilia
    Brena, Beatriz
    Seoane, Gustavo
    Gonzalez, David
    SYNTHETIC COMMUNICATIONS, 2007, 37 (19-21) : 3509 - 3518
  • [4] Chemoenzymatic synthesis and biological evaluation of α-Gal epitopes and their derivatives.
    Wang, PG
    Pang, JW
    Chen, X
    Zhang, W
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U43 - U43
  • [5] Novel triazole 2′-deoxy-4′-thionucleosides:: Stereoselective synthesis and biological evaluation
    Inguaggiato, G
    Jasamai, M
    Smith, JE
    Slater, M
    Simons, C
    NUCLEOSIDES & NUCLEOTIDES, 1999, 18 (03): : 457 - 467
  • [6] Synthesis and Biological Evaluation of Novel 6-Deoxy-β-D-Psicofuranosyl Mercaptoheterocyclic Compounds
    De lade, I. G.
    Braga, F. G.
    Grazul, R. M.
    Coimbra, E. S.
    Da Silva, A. D.
    LETTERS IN DRUG DESIGN & DISCOVERY, 2008, 5 (08) : 481 - 484
  • [7] Synthesis and Biological Evaluation of 7-Deoxy-Epothilone Analogues
    Woods, Laura M.
    Arico, Joseph W.
    Frein, Jeffrey D.
    Sackett, Dan L.
    Taylor, Richard E.
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2017, 18 (03)
  • [8] Total Synthesis and Biological Evaluation of (-)-9-Deoxy-englerin A
    Ushakov, Dmitry B.
    Navickas, Vaidotas
    Stroebele, Markus
    Maichle-Moessmer, Caecilia
    Sasse, Florenz
    Maier, Martin E.
    ORGANIC LETTERS, 2011, 13 (08) : 2090 - 2093
  • [9] Synthesis of novel 3-deoxy-3-C-triazolylmethyl-allose derivatives and evaluation of their biological activity
    Rjabova, Jekaterina
    Rjabovs, Vitalijs
    Moreno Vargas, Antonio J.
    Moreno Clavijo, Elena
    Turks, Maris
    CENTRAL EUROPEAN JOURNAL OF CHEMISTRY, 2012, 10 (02): : 386 - 394
  • [10] Chemoenzymatic synthesis, structural study and biological activity of novel indolizidine and quinolizidine iminocyclitols
    Gomez, Livia
    Garrabou, Xavier
    Joglar, Jesus
    Bujons, Jordi
    Parella, Teodor
    Vilaplana, Cristina
    Joan Cardona, Pere
    Clapes, Pere
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (31) : 6309 - 6321