7-(AMINOETHYL) ETHER AND THIOETHER OF DAUNOMYCINONE

被引：15

作者：

ACTON, EM

TONG, GL

MOSHER, CW

SMITH, TH

HENRY, DW

机构：

[1] Bio-Organic Chemistry Laboratory, SRI International, Menlo Park

[2] Burroughs Wellcome Co., Research Triangle Park

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 1979年 / 22卷 / 08期

关键词：

D O I：

10.1021/jm00194a007

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

One-step treatment of daunomycinone with excess 2-aminoethanethiol and 2-aminoethanol in trifluoroacetic acid afforded at C-7 the thioether (77% yield) and ether (30% after recycling), respectively. Stereoselectivity for the natural IS over the 1R configuration was greater for the ether (97:3) than for the thioether (2.5:1). Esterification of daunomycin at C-7 with β-alanine was accomplished through the mixed anhydride of Z(OMe)-β-alanine. Preliminary biological tests suggest that the antitumor and DNA interactive properties of the anthracyclines can be retained in such structures. © 1979, American Chemical Society. All rights reserved.

引用

页码：922 / 926

页数：5

共 18 条

[1] DAUNOMYCIN .I. STRUCTURE OF DAUNOMYCINONE [J].