Synthesis and antiviral activity of novel acyclic nucleosides in the 5-alkynyl- and 6-alkylfuro[2,3-d]pyrimidine series

被引：57

作者：

Amblard, F

Aucagne, V

Guenot, P

Schinazi, RF

Agrofoglio, LA

机构：

[1] ICOA, UMR 6005, UFR Sci, Inst Chim Organ & Analyt, F-45067 Orleans 2, France

[2] Univ Rennes 1, CRMPO, F-35042 Rennes, France

[3] Emory Univ, Biochem Pharmacol Lab, Dept Pediat, Sch Med, Atlanta, GA 30033 USA

[4] Emory Univ, Sch Med, Vet Affairs Med Ctr, Atlanta, GA 30033 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2005年 / 13卷 / 04期

基金：

美国国家科学基金会;

关键词：

nucleosides; furopyrimidine; antiviral activity;

D O I：

10.1016/j.bmc.2004.11.057

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The synthesis of novel acyclic nucleosides in the 5-alkynyl and 6-alkylfuro[2,3-d]pyrimidine series is described. These compounds were evaluated against HIV and HSV in order to determine their spectrum of antiviral activity. Their cytotoxicities against PBM, CEM and VERO cells were also determined. Compounds 21d and 24b displayed moderate EC50S of 2.7 and 4.9 muM, respectively, against HIV-1 and of 6.3 and 4.8 muM, respectively, against HSV. Nevertheless, these compounds also showed cellular toxicity, suggesting that the antiviral effects are secondary to the toxic effects. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：1239 / 1248

页数：10

共 48 条

[1] Agrofoglio L, 1998, ACYCLIC CARBOCYCLIC
[2] Palladium-assisted routes to nucleosides
Agrofoglio, LA
Gillaizeau, I
Saito, Y
[J]. CHEMICAL REVIEWS, 2003, 103 (05) : 1875 - 1916
[3] Efficient synthesis of various acycloalkenyl derivatives of pyrimidine using cross-metathesis and Pd(0) methodologies
Amblard, F
Nolan, SP
Schinazi, RF
Agrofoglio, LA
[J]. TETRAHEDRON, 2005, 61 (03) : 537 - 544
[4] A new route to acyclic nucleosides via palladium-mediated allylic alkylation and cross-metathesis
Amblard, F
Nolan, SP
Gillaizeau, I
Agrofoglio, LA
[J]. TETRAHEDRON LETTERS, 2003, 44 (51) : 9177 - 9180
[5] CERIUM(IV)-MEDIATED HALOGENATION AT C-5 OF URACIL DERIVATIVES
ASAKURA, J
ROBINS, MJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (16) : 4928 - 4933
[6] Highly efficient AgNO3-catalyzed preparation of substituted furanopyrimidine nucleosides
Aucagne, V
Amblard, F
Agrofoglio, LA
[J]. SYNLETT, 2004, (13) : 2406 - 2408
[7] BLEACKLEY RC, 1976, TETRAHEDRON, V32, P2795, DOI 10.1016/0040-4020(76)80125-1
[8] POTENTIAL INHIBITORS OF S-ADENOSYLMETHIONINE-DEPENDENT METHYLTRANSFERASES .11. MOLECULAR DISSECTIONS OF NEPLANOCIN-A AS POTENTIAL INHIBITORS OF S-ADENOSYLHOMOCYSTEINE HYDROLASE
BORCHERDING, DR
NARAYANAN, S
HASOBE, M
MCKEE, JG
KELLER, BT
BORCHARDT, RT
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (09) : 1729 - 1738
[9] INDOLES BENZOFURANS PHTHALIDES AND TOLANES VIA COPPER(1) ACETYLIDES
CASTRO, CE
GAUGHAN, EJ
OWSLEY, DC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (12) : 4071 - +
[10] CHEMISTRY AND ANTIVIRAL ACTIVITIES OF ACYCLONUCLEOSIDES
CHU, CK
CUTLER, SJ
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (02) : 289 - 319

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