SYNTHESIS OF 4-AMINO SUBSTITUTED AND 4-UNSUBSTITUTED 1,10-PHENANTHROLINE-3-CARBOXYLIC ACID-DERIVATIVES AS POTENTIAL DNA CLEAVAGE REAGENTS

被引:5
作者
CHIU, FCK
BROWNLEE, RTC
PHILLIPS, DR
机构
[1] LA TROBE UNIV, CTR PROT & ENZYME TECHNOL, BUNDOORA, VIC 3083, AUSTRALIA
[2] LA TROBE UNIV, DEPT BIOCHEM, BUNDOORA, VIC 3083, AUSTRALIA
关键词
D O I
10.1016/S0040-4020(01)80803-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of several new 4-amino substituted and 4-unsubstituted 1,10-phenanthroline-3-carboxylic acid derivatives are reported. The 4-amino derivatives (5,6,7) were prepared from 1,4-dihyro-4-oxo-1,10-phenanthroline-3-carboxylic acid (2) via aromatization and 4-chlorination, followed by nucleophilic substitution at C4 by the appropiate alkyl amine. The 4-unsubstituted derivatives (10,11,12) were prepared by aromatization and 4-chlorination of ethyl 1,4-dihydro-1-oxo-1,10-phenanthroline-3-carboxylate. The substituent at C4 was removed by conversion to the 4-tosyl hydrazide, followed by base-catalysed elimination of the hydrazide group. These phenanthroline derivatives were designed as metal-ion-complex mediated DNA cleavage reagents. In both series the 3-carboxylic acid side chain was coupled to beta-alanine to facilitate its conjugation with DNA binding molecules.
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收藏
页码:889 / 894
页数:6
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