Synthesis and antiviral activity of a series of 1′-substituted 4-aza-7,9-dideazaadenosine C-nucleosides

被引：168

作者：

Cho, Aesop ^{[1
]}

Saunders, Oliver L. ^{[1
]}

Butler, Thomas ^{[1
]}

Zhang, Lijun ^{[1
]}

Xu, Jie ^{[1
]}

Vela, Jennifer E. ^{[1
]}

Feng, Joy Y. ^{[1
]}

Ray, Adrian S. ^{[1
]}

Kim, Choung U. ^{[1
]}

机构：

[1] Gilead Sci Inc, Foster City, CA 94044 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2012年 / 22卷 / 08期

关键词：

C-nucleoside; Antiviral; Polymerase inhibitor; ANALOG;

D O I：

10.1016/j.bmcl.2012.02.105

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of 1 '-substituted analogs of 4-aza-7,9-dideazaadenosine C-nucleoside were prepared and evaluated for the potential as antiviral agents. These compounds showed a broad range of inhibitory activity against various RNA viruses. In particular, the whole cell potency against HCV when R = CN was attributed to inhibition of HCV NS5B polymerase and intracellular concentration of the corresponding nucleoside triphosphate. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：2705 / 2707

页数：3

共 13 条

[1] SYNTHESIS OF 5-SUBSTITUTED PYRIMIDINES .2.
ASBUN, W
BINKLEY, SB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (01) : 140 - &
[2] Ribose-modified nucleosides as ligands for adenosine receptors:: Synthesis, conformational analysis, and biological evaluation of 1′-C-methyl adenosine analogues
Cappellacci, L
Barboni, G
Palmieri, M
Pasqualini, M
Grifantini, M
Costa, B
Martini, C
Franchetti, P
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (06) : 1196 - 1202
[3] Nucleoside and nucleotide HIV reverse transcriptase inhibitors: 25 years after zidovudine
Cihlar, Tomas
Ray, Adrian S.
[J]. ANTIVIRAL RESEARCH, 2010, 85 (01) : 39 - 58
[4] Synthesis of 1′-C-fluoromethyladenosine
Damont, Annelaure
Dukhan, David
Gosselin, Gilles
Peyronnet, Jerome
Storer, Richard
[J]. NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2007, 26 (10-12) : 1431 - 1434
[5] Antitumor activity of C-methyl-β-D-ribofuranosyladenine nucleoside ribonucleotide reductase inhibitors
Franchetti, P
Cappellacci, L
Pasqualini, M
Petrelli, R
Vita, P
Jayaram, HN
Horvath, Z
Szekeres, T
Grifantini, M
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (15) : 4983 - 4989
[6] An Improved One-Pot Synthesis of Nucleoside 5'-Triphosphate Analogues
Gillerman, Irina
Fischer, Bilha
[J]. NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2010, 29 (03) : 245 - 256
[7] MONONUCLEOSIDE PHOSPHOTRIESTER DERIVATIVES WITH S-ACYL-2-THIOETHYL BIOREVERSIBLE PHOSPHATE-PROTECTING GROUPS - INTRACELLULAR DELIVERY OF 3'-AZIDO-2',3'-DIDEOXYTHYMIDINE 5'-MONOPHOSPHATE
LEFEBVRE, I
PERIGAUD, C
POMPON, A
AUBERTIN, AM
GIRARDET, JL
KIRN, A
GOSSELIN, G
IMBACH, JL
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (20) : 3941 - 3950
[8] Practical synthesis of 1′-substituted Tubercidin C-nucleoside analogs
Metobo, Sammy E.
Xu, Jie
Saunders, Oliver L.
Butler, Thomas
Aktoudianakis, Evangelos
Cho, Aesop
Kim, Choung U.
[J]. TETRAHEDRON LETTERS, 2012, 53 (05) : 484 - 486
[9] O'Connor S.J., 2007, [No title captured], Patent No. [WO200756170, 200756170]
[10] A 7-deaza-adenosine analog is a potent and selective inhibitor of hepatitis C virus replication with excellent pharmacokinetic properties
Olsen, DB
Eldrup, AB
Bartholomew, L
Bhat, B
Bosserman, MR
Ceccacci, A
Colwell, LF
Fay, JF
Flores, OA
Getty, KL
Grobler, JA
LaFemina, RL
Markel, EJ
Migliaccio, G
Prhavc, M
Stahlhut, MW
Tomassini, JE
MacCoss, M
Hazuda, DJ
Carroll, SS
[J]. ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2004, 48 (10) : 3944 - 3953

← 1 2 →