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

被引:6
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 [J].
Bello, Angelica M. ;
Poduch, Ewa ;
Liu, Yan ;
Wei, Lianhu ;
Crandall, Ian ;
Wang, Xiaoyang ;
Dyanand, Christopher ;
Kain, Kevin C. ;
Pai, Emil F. ;
Kotra, Lakshmi P. .
JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (03) :439-448
[2]   Structure-activity relationships of uridine 5′-diphosphate analogues at the human P2Y6 receptor [J].
Besada, Pedro ;
Shin, Dae Hong ;
Costanzi, Stefano ;
Ko, Hyojin ;
Mathe, Christophe ;
Gagneron, Julien ;
Gosselin, Gilles ;
Maddileti, Savitri ;
Harden, T. Kendall ;
Jacobson, Kenneth A. .
JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (18) :5532-5543
[3]   Kinetic properties of the acylneuraminate cytidylyltransferase from Pasteurella haemolytica A2 [J].
Bravo, IG ;
Barrallo, S ;
Ferrero, MA ;
Rodriguez-Aparicio, LB ;
Martínez-Blanco, H ;
Reglero, A .
BIOCHEMICAL JOURNAL, 2001, 358 (358) :585-598
[4]   Stereoselective synthesis of the 5′-hydroxy-5′-phosphonate derivatives of cytidine and cytosine arabinoside [J].
Chen, XM ;
Wiemer, AJ ;
Hohl, RJ ;
Wiemer, DF .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (26) :9331-9339
[5]   FULLY SYNTHETIC STEREOSELECTIVE ROUTES TO THE DIFFERENTIALLY PROTECTED SUBUNITS OF THE TUNICAMYCINS [J].
DANISHEFSKY, SJ ;
DENINNO, SL ;
CHEN, S ;
BOISVERT, L ;
BARBACHYN, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (15) :5810-5818
[6]   A novel reagent for the synthesis of geminal di-sulfones [J].
Hadd, MJ ;
Smith, MA ;
Gervay-Hague, 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 [J].
MANDRELL, RE ;
APICELLA, MA .
IMMUNOBIOLOGY, 1993, 187 (3-5) :382-402
[10]   Molecular mimicry of host structures by bacterial lipopolysaccharides and its contribution to disease [J].
Moran, AP ;
Prendergast, MM ;
Appelmelk, BJ .
FEMS IMMUNOLOGY AND MEDICAL MICROBIOLOGY, 1996, 16 (02) :105-115