SELECTIVITY IN NUCLEOSIDE ALKYLATION AND ARALKYLATION IN RELATION TO CHEMICAL CARCINOGENESIS

被引：92

作者：

MOSCHEL, RC ^{[1
]}

HUDGINS, WR ^{[1
]}

DIPPLE, A ^{[1
]}

机构：

[1] NCI,FREDERICK CANC RES CTR,PROGRAM CHEM CARCINOGENESIS,FREDERICK,MD 21701

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 19期

关键词：

D O I：

10.1021/jo01333a010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The sites of benzylation of adenosine and guanosine by different benzylating agents in various solvent mixtures were investigated in order to determine those properties of chemical reactivity which lead to reaction on the exocyclic amino and oxo groups. Modification of these sites, as opposed to ring nitrogen sites, can be associated with carcinogenic potential, and was found to be favored by changes in reaction medium or leaving group which would advance carbon leaving group bond breakage. The extents of reaction on the exocyclic amino group of guanosine were greater than for the exocyclic O1 23456 site but the ratio of reaction at 06 8/N2 increased with increasing leaving group hardness, suggesting that the charge localization or hardness of the reaction center determines the distribution of products over these two sites. © 1979, American Chemical Society. All rights reserved.

引用

页码：3324 / 3328

页数：5

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