Synthesis and antiviral evaluation of α-D-2′,3′-didehydro-2′,3′-dideoxy-3′-C-hydroxymethyl nucleosides

被引：3

作者：

Yamada, Kohei ^{[1
]}

Hayakawa, Hiroyuki ^{[1
]}

Sakata, Shinji ^{[1
]}

Ashida, Noriyuki ^{[1
]}

Yoshimura, Yuichi ^{[2
]}

机构：

[1] Yamasa Corp, Div Biochem, Chiba 2880056, Japan

[2] Tohoku Pharmaceut Univ, Aoba Ku, Sendai, Miyagi 9818558, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2010年 / 20卷 / 20期

关键词：

Nucleosides; Antiviral; S(N)2 ' Reaction; PYRIMIDINE NUCLEOSIDES; ALTERNATIVE SYNTHESIS; BIOLOGICAL-ACTIVITIES; ALLYLIC SELENIDES; SUGAR MOIETY; NUCLEOTIDES; OXETANOCIN; HIV; AGENTS; ISONUCLEOSIDES;

D O I：

10.1016/j.bmcl.2010.08.071

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

We have identified a selective S(N)2' reaction triggered by iodide ion that leads to the ring-opening of 2,2'-anhydro-alpha-nucleosides. By applying the method, we have synthesized alpha-D-2',3'-didehydro-2',3'-dideoxy- 3'-C-hydroxymethyl nucleosides, designed as potential antiviral agents. (c) 2010 Elsevier Ltd. All rights reserved.

引用

页码：6013 / 6016

页数：4

共 50 条

[41] SYNTHESIS OF SOME 2',3'-DIDEOXY-3'-C-FLUOROMETHYL AND 3'-C-AZIDOMETHYL NUCLEOSIDES
SVANSSON, L
KVARNSTROM, I
CLASSON, B
SAMUELSSON, B
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 1992, 11 (07): : 1353 - 1366
[42] SYNTHESIS OF 2'-CHLORO-2',3'-DIDEOXY-2',3'-DIDEHYDRO NUCLEOSIDES
VANAERSCHOT, A
HERDEWIJN, P
BULLETIN DES SOCIETES CHIMIQUES BELGES, 1989, 98 (12): : 931 - 936
[43] Synthesis of 2',3'-dideoxy-3'-hydroxymethylcytidine; A unique antiviral nucleoside
Faul, MM
Huff, BE
Dunlap, SE
Frank, SA
Fritz, JE
Kaldor, SW
LeTourneau, ME
Staszak, MA
Ward, JA
Werner, JA
Winneroski, LL
TETRAHEDRON, 1997, 53 (24) : 8085 - 8104
[44] Synthesis of the antiviral nucleoside 2',3'-dideoxy-3'-hydroxymethylcytidine.
Brennan, J
Dunlap, SE
Faul, MM
Frank, SA
Fritz, JE
Huff, BE
Kaldor, SW
LeTourneau, ME
Miller, WD
Sullivan, KA
Staszak, MA
Ward, JA
Werner, JA
Winneroski, LL
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 211 : 185 - ORGN
[45] Synthesis and antiviral activity of prodrugs of the nucleoside 1-[2′,3′-dideoxy-3′-C-(hydroxymethyl)-β-D-erythropentofuranosyl] cytosine
Mauldin, SC
Paget, CJ
Jones, CD
Colacino, JM
Baxter, AJ
Staschke, KA
Johansson, NG
Vrang, L
BIOORGANIC & MEDICINAL CHEMISTRY, 1998, 6 (05) : 577 - 585
[46] SYNTHESIS AND ANTI-HIV ACTIVITY OF CARBOCYCLIC 2',3'-DIDEHYDRO-2',3'-DIDEOXY 2,6-DISUBSTITUTED PURINE NUCLEOSIDES
VINCE, R
HUA, M
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (01) : 17 - 21
[47] L-2′,3′-Didehydro-2′,3′-dideoxy-3′-fluoronucleosides:: Synthesis, anti-HIV activity, chemical and enzymatic stability, and mechanism of resistance
Chong, Y
Gumina, G
Mathew, JS
Schinazi, RF
Chu, CK
JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (15) : 3245 - 3256
[48] THE SYNTHESIS OF NOVEL CARBOHYDRATES AMENABLE TO THE SYNTHESIS OF 2',3'-DIDEOXY-3'-BRANCHED NUCLEOSIDES
PUDLO, JS
TOWNSEND, LB
NUCLEOSIDES & NUCLEOTIDES, 1992, 11 (2-4): : 279 - 293
[49] Synthesis of 2′,3′-dideoxy-2′,3′-didehydro nucleosides via a serendipitous route
Guo, Z
Sanghvi, YS
Brammer, LE
Hudlicky, T
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2001, 20 (4-7): : 1263 - 1266
[50] Synthesis and anti-HIV-1 evaluation of phosphonates which mimic the 5′-monophosphate of 4′-branched 2′,3′-didehydro-2′,3′-dideoxy nucleosides
Kubota, Yutaka
Ishizaki, Nobuhide
Haraguchi, Kazuhiro
Hamasaki, Takayuki
Baba, Masanori
Tanaka, Hiromichi
BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (20) : 7186 - 7192

← 1 2 3 4 5 →