5′-Homoaristeromycin.: Synthesis and antiviral activity against orthopox viruses

被引：29

作者：

Yang, MM ^{[1
]}

Schneller, SW ^{[1
]}

机构：

[1] Auburn Univ, Dept Chem & Biochem, Auburn, AL 36849 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2005年 / 15卷 / 01期

基金：

美国国家卫生研究院;

关键词：

carbocyclic nucleosides; nucleoside homologation; monkeypox;

D O I：

10.1016/j.bmcl.2004.10.019

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

An efficient synthesis of 5'-homoaristeromycin has been developed. This permitted an extensive antiviral analysis, which found potent activity toward vaccinia, cowpox, and monkeypox viruses. For comparative purposes, 5'-homoadenosine was made available by a newly designed route and found to be inactive. (C) 2004 Elsevier Ltd. All rights reserved.

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页码：149 / 151

页数：3

相关论文

共 24 条

[1]

[Anonymous], 1996, ADV ANTIVIRAL DRUG D

[2] Potential antiviral therapeutics for smallpox, monkeypox and other orthopoxvirus infections [J].

Baker, R ;

Bray, M ;

Huggins, JW .

ANTIVIRAL RESEARCH, 2003, 57 (1-2) :13-23

[3]

BENNETT LL, 1986, MOL PHARMACOL, V29, P383

[4] EVIDENCE THAT THE CARBOCYCLIC ANALOG OF ADENOSINE HAS DIFFERENT MECHANISMS OF CYTOTOXICITY TO CELLS WITH ADENOSINE KINASE-ACTIVITY AND TO CELLS LACKING THIS ENZYME [J].

BENNETT, LL ;

BOWDON, BJ ;

ALLAN, PW ;

ROSE, LM .

BIOCHEMICAL PHARMACOLOGY, 1986, 35 (22) :4106-4109

[5] Antiviral prophylaxis of smallpox [J].

Bray, M ;

Roy, CJ .

JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 2004, 54 (01) :1-5

[6] Strategies in the design of antiviral drugs [J].

De Clercq, E .

NATURE REVIEWS DRUG DISCOVERY, 2002, 1 (01) :13-25

[7] (1'R,2'S,3'R)-9-(2',3'-DIHYDROXYCYCLOPENTAN-1'-YL)-ADENINE AND 3-DEAZA-ADENINE - ANALOGS OF ARISTEROMYCIN WHICH EXHIBIT POTENT ANTIVIRAL ACTIVITY WITH REDUCED CYTOTOXICITY [J].

HASOBE, M ;

LIANG, H ;

AULTRICHE, DB ;

BORCHERDING, DR ;

WOLFE, MS ;

BORCHARDT, RT .

ANTIVIRAL CHEMISTRY & CHEMOTHERAPY, 1993, 4 (04) :245-248

[8] Synthetic studies towards (+/-)-aristeromycin and its 5'-homo-analogue [J].

Kapeller, H ;

Baumgartner, H ;

Griengl, H .

MONATSHEFTE FUR CHEMIE, 1997, 128 (02) :191-200

[9] RATIONAL APPROACHES TO THE DESIGN OF ANTIVIRAL AGENTS BASED ON S-ADENOSYL-L-HOMOCYSTEINE HYDROLASE AS A MOLECULAR TARGET [J].

LIU, S ;

WOLFE, MS ;

BORCHARDT, RT .

ANTIVIRAL RESEARCH, 1992, 19 (03) :247-265

[10] Highly stereoselective synthesis of carbocycles via a radical addition reaction using 2,2′-azobis(2,4-dimethyl-4-methoxyvaleronitrile) [V-70L] [J].

Matsugi, M ;

Gotanda, K ;

Ohira, C ;

Suemura, M ;

Sano, A ;

Kita, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (18) :6928-6930