Synthesis and anti-HCV activity of 1-(1′,3′-O-anhydro-3′-C-methyl-β-D-psicofuranosyl)uracil

被引：2

作者：

Komsta, Zofia ^{[2
]}

Mayes, Benjamin ^{[1
]}

Moussa, Adel ^{[1
]}

Shelbourne, Montserrat ^{[2
]}

Stewart, Alistair ^{[1
]}

Tyrrell, Andrew J. ^{[2
]}

Wallis, Laura L. ^{[2
]}

Weymouth-Wilson, Alexander C. ^{[2
]}

Yurek-George, Alexander ^{[2
]}

机构：

[1] Idenix Pharmaceut, Cambridge, MA 02141 USA

[2] Dextra, Ctr Sci & Technol, Reading RG6 6BZ, Berks, England

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 45期

关键词：

HCV; Psicose; Oxetane; Bicyclic ribonucleosides; Conformational restriction; NUCLEIC-ACID; NUCLEOSIDE SYNTHESES; RIBONUCLEOSIDES; PRODRUG; ANALOGS;

D O I：

10.1016/j.tetlet.2014.09.069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of a novel 1',2'-oxetane-uridine bearing a 2'-C-methyl substituent, [1-(1',3'-O-anhydro-3'-Cmethyl-beta-D-psicofuranosyl)uracil], is described. Key to its construction was the use of 6-O-(p-toluoy1)1,2:3,4-di-O-isopropylidene-3-C-methyl-D-psicofuranose as a nucleosidation substrate, which itself was derived from D-fructose. Anti-HCV activity was examined for the corresponding triphosphate which was not found to be an inhibitor of HCV NS5B 1b wild type polymerase in vitro. The 1',2'-oxetane uridine triphosphate without 2'-C-methyl substitution was similarly inactive, however, the guanosine analog displayed modest inhibition (IC50= 10 mu M). (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：6216 / 6219

页数：4

共 50 条

[21] NUCLEOSIDES .7. SYNTHESIS AND CONFORMATION OF 1-(3-AMINO-3-DESOXY-BETA-D-GALACTOPYRANOSYL)-URACIL
LICHTENTHALER, FW
BAMBACH, G
SCHEIDEG.U
CHEMISCHE BERICHTE-RECUEIL, 1969, 102 (03): : 986 - +
[22] BRANCHED-CHAIN SUGARS .12. SYNTHESIS OF 3,4-ANHYDRO-1-DEOXY-3-C-METHYL-D-HEXULOSE DERIVATIVES
CUBERO, II
LOPEZESPINOSA, MTP
CARBOHYDRATE RESEARCH, 1986, 154 : 71 - 80
[23] SYNTHESIS AND IN VITRO ACTIVITY EVALUATION OF 2′,3′-C-DIMETHYL CARBOCYCLIC NUCLEOSIDE ANALOGUES AS POTENTIAL ANTI-HCV AGENTS
Ko, Ok Hyun
Hong, Joon Hee
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2009, 28 (08): : 761 - 771
[24] GLYCOSYLATION OF LACTOSE - SYNTHESIS OF METHYL O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-(1-]3)-O-BETA-D-GALACTOPYRANOSYL-(1-]4)-BETA-D-GLUCOPYRANOSIDE AND METHYL O-BETA-D-GALACTOPYRANOSYL-(1-]4)-O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-(1-]3)-O-BETA-D-GALACTOPYRANOSYL-(1-]4)-BETA-D-GLUCOPYRANOSIDE
MARANDUBA, A
VEYRIERES, A
CARBOHYDRATE RESEARCH, 1985, 135 (02) : 330 - 336
[25] Synthesis, evaluation of anti-HIV-1 and anti-HCV activity of novel 2′,3′-dideoxy-2′,2′-difluoro-4′-azanucleosides
Martinez-Montero, Saul
Fernandez, Susana
Sanghvi, Yogesh S.
Theodorakis, Emmanuel A.
Detorio, Mervi A.
Mcbrayer, Tamara R.
Whitaker, Tony
Schinazi, Raymond F.
Gotor, Vicente
Ferrero, Miguel
BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (23) : 6885 - 6893
[26] PHOSPHONO NUCLEOSIDE .1. SYNTHESIS OF 2,3'-ANHYDRO-1'-DEOXY-1'-PHOSPHONO-1-BETA-D-FRUCTOFURANOSYL URACIL
TATSUOKA, T
IMAO, K
SUZUKI, K
HETEROCYCLES, 1986, 24 (03) : 617 - 620
[27] REGIOSELECTIVELY MODIFIED STEREOREGULAR POLYSACCHARIDES .14. SYNTHESIS OF A C-METHYLATED LINEAR DEXTRAN 3-C-METHYL-3-O-METHYL-(1-]6)-ALPHA-D-GLUCOPYRANAN
KOBAYASHI, K
SUMITOMO, H
TAKAHASHI, M
POLYMER JOURNAL, 1989, 21 (07) : 559 - 565
[28] SYNTHESIS OF PYRIMIDIC NUCLEOSIDES FROM 1,2-ANHYDRO-4-DEOXY-3-O-METHYL-PENTOPYRANOSES
GAGNIEU, CH
GROUILLER, AV
PACHECO, H
CARBOHYDRATE RESEARCH, 1983, 114 (02) : 193 - 200
[29] STRUCTURE OF 1-(3-DEOXY-3-PHENYLSELENO-2,5-DI-O-PIVALOYL-BETA-D-XYLOFURANOSYL)URACIL
YAMAGUCHI, K
MATSUMURA, G
HARAGUCHI, K
ITOH, Y
TANAKA, H
MIYASAKA, T
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1992, 48 : 387 - 389
[30] EPOXIDATIONS WITH TRIPHENYLPHOSPHINE AND DIETHYL AZODICARBOXYLATE .1. SYNTHESIS OF METHYL 3,4-ANHYDRO-D-TAGATOFURANOSIDES
GUTHRIE, RD
JENKINS, ID
YAMASAKI, R
SKELTON, BW
WHITE, AH
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (08): : 2328 - 2334

← 1 2 3 4 5 →