Synthesis of Triazenopyrazole Derivativesas Potential Inhibitors of HIV-1Synthese von Triazenopyrazolderivaten als potentielle Inhibitoren von HIV-1

被引：29

作者：

Janus S. Larsen

Magdy A. Zahran

Erik B. Pedersen

Claus Nielsen

机构：

[1] Department of Chemistry,

[2] Odense University,undefined

[3] DK-5230 Odense M,undefined

[4] Denmark,undefined

[5] Retrovirus Laboratory,undefined

[6] Department of Virology,undefined

[7] Statens Seruminstitut,undefined

[8] DK-2300 Copenhagen,undefined

[9] Denmark,undefined

来源：

Monatshefte für Chemie / Chemical Monthly | 1999年 / 130卷 / 9期

关键词：

Keywords. Triazenopyrazoles; Nucleosides; convergent synthesis of; Nucleosides; 1-(5-triazeno)pyrazole; Nucleosides; 2-(5-triazeno)pyrazole; Human immunodeficiency virus; Herpes simplex virus.;

D O I：

10.1007/PL00010295

中图分类号：

学科分类号：

摘要：

Ethoxymethylenemalononitrile and bis(methylthio)methylenemalononitrile were condensed with hydrazine hydrate to yield 5-aminopyrazole-4-carbonitrile (3a) and 5-amino-3-methylthiopyrazole-4-carbonitrile (3b), respectively. These compounds were treated with nitrous acid and coupled with different secondary amines to yield the triazenopyrazoles 4a–j. 5-(3,3-Diethyl-1-triazeno)pyrazole-4-carbonitrile (4c) was transferred into its two regioisomeric 2-deoxyribose nucleosides 5a,b which were subsequently hydrolyzed with H2O2/OH− to give the corresponding carboxamides 6a,b. All synthesized compounds were tested for biological activity against HIV-1 and herpes simplex virus, but only 4c showed moderate activity against HIV-1 with ED50=32μM.

引用

页码：1167 / 1173

页数：6