Synthesis of sulfone-based nucleotide isosteres: identification of CMP-sialic acid synthetase inhibitors

被引:5
作者
Wong, Jessica H. [1 ]
Sahni, Urvashi [1 ]
Li, Yanhong [1 ]
Chen, Xi [1 ]
Gervay-Hague, Jacquelyn [1 ]
机构
[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA
关键词
N-ACETYLNEURAMINIC ACID; MOLECULAR MIMICRY; DERIVATIVES; OLIGOSACCHARIDES; CYTIDINE; ANALOGS;
D O I
10.1039/b819155g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A modular replacement approach to the synthesis of sulfonucleotide analogs prepared from condensation of nucleoside aldehydes with bis phosphonate Horner-Wadsworth-Emmons reagents is disclosed. These analogs were shown to be inhibitors of Neisseria meningitidis CSS (NmCSS), which is a key enzyme in the biosynthesis of the capsular polysaccharides required for bacterial infection.
引用
收藏
页码:27 / 29
页数:3
相关论文
共 24 条
  • [1] Structure-activity relationships of C6-uridine derivatives targeting Plasmodia orotidine monophosphate decarboxylase
    Bello, Angelica M.
    Poduch, Ewa
    Liu, Yan
    Wei, Lianhu
    Crandall, Ian
    Wang, Xiaoyang
    Dyanand, Christopher
    Kain, Kevin C.
    Pai, Emil F.
    Kotra, Lakshmi P.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (03) : 439 - 448
  • [2] Structure-activity relationships of uridine 5′-diphosphate analogues at the human P2Y6 receptor
    Besada, Pedro
    Shin, Dae Hong
    Costanzi, Stefano
    Ko, Hyojin
    Mathe, Christophe
    Gagneron, Julien
    Gosselin, Gilles
    Maddileti, Savitri
    Harden, T. Kendall
    Jacobson, Kenneth A.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (18) : 5532 - 5543
  • [3] Kinetic properties of the acylneuraminate cytidylyltransferase from Pasteurella haemolytica A2
    Bravo, IG
    Barrallo, S
    Ferrero, MA
    Rodriguez-Aparicio, LB
    Martínez-Blanco, H
    Reglero, A
    [J]. BIOCHEMICAL JOURNAL, 2001, 358 (358) : 585 - 598
  • [4] Stereoselective synthesis of the 5′-hydroxy-5′-phosphonate derivatives of cytidine and cytosine arabinoside
    Chen, XM
    Wiemer, AJ
    Hohl, RJ
    Wiemer, DF
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (26) : 9331 - 9339
  • [5] FULLY SYNTHETIC STEREOSELECTIVE ROUTES TO THE DIFFERENTIALLY PROTECTED SUBUNITS OF THE TUNICAMYCINS
    DANISHEFSKY, SJ
    DENINNO, SL
    CHEN, S
    BOISVERT, L
    BARBACHYN, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (15) : 5810 - 5818
  • [6] A novel reagent for the synthesis of geminal di-sulfones
    Hadd, MJ
    Smith, MA
    Gervay-Hague, J
    [J]. TETRAHEDRON LETTERS, 2001, 42 (31) : 5137 - 5140
  • [7] Knorst M, 2001, ADV SYNTH CATAL, V343, P698, DOI 10.1002/1615-4169(200108)343:6/7<698::AID-ADSC698>3.0.CO
  • [8] 2-J
  • [9] LIPO-OLIGOSACCHARIDES (LOS) OF MUCOSAL PATHOGENS - MOLECULAR MIMICRY AND HOST-MODIFICATION OF LOS
    MANDRELL, RE
    APICELLA, MA
    [J]. IMMUNOBIOLOGY, 1993, 187 (3-5) : 382 - 402
  • [10] Molecular mimicry of host structures by bacterial lipopolysaccharides and its contribution to disease
    Moran, AP
    Prendergast, MM
    Appelmelk, BJ
    [J]. FEMS IMMUNOLOGY AND MEDICAL MICROBIOLOGY, 1996, 16 (02): : 105 - 115