ALKYLATING NUCLEOSIDES .2. SYNTHESIS AND CYTOSTATIC ACTIVITY OF BROMOMETHYLPYRAZOLE AND PYRAZOLE NITROGEN-MUSTARD NUCLEOSIDES

被引：16

作者：

GARCIALOPEZ, MT

HERRANZ, R

ALONSO, G

机构：

[1] Instituto de Química Médica, Juan de la Cierva, Madrid

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 1979年 / 22卷 / 07期

关键词：

D O I：

10.1021/jm00193a011

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Glycosylation of ethyl 3(5)-(bromomethyl)pyrazole-5(3)-carboxylate (3) and 3(5)-(bromomethyl)pyrazole-5(3)-carboxamide (4) with poly-O-acetylated sugars via an acid-catalyzed fusion method afforded the corresponding ethyl 3-(bromomethyl)pyrazole-5-carboxylate and 3-(bromomethyl)pyrazole-5-carboxamide substituted nucleosides 5 and 7, respectively. In some cases, the positional isomers 6 and 8 were also obtained. Treatment of 5 and 7 with methanolic ammonia gave the deprotected 3-(aminomethyl)pyrazole-5-carboxamide nucleosides 9. Reaction of 3-5 and 7 with bis(2-chloroethyl)amine led to the corresponding pyrazole nitrogen mustards 10-13. All the bromomethylpyrazole nucleosides described showed significant cytostatic activity against HeLa cell cultures. © 1979, American Chemical Society. All rights reserved.

引用

页码：807 / 811

页数：5