BENZOPORPHYRIN DERIVATIVES - SYNTHESIS, STRUCTURE AND PRELIMINARY BIOLOGICAL-ACTIVITY

被引:18
作者
MEUNIER, I
PANDEY, RK
SENGE, MO
DOUGHERTY, TJ
SMITH, KM
机构
[1] UNIV CALIF DAVIS,DEPT CHEM,DAVIS,CA 95616
[2] ROSWELL PK CANC INST,PDT CTR,DEPT RADIAT BIOL,DIV CHEM,BUFFALO,NY 14263
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 08期
关键词
D O I
10.1039/p19940000961
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Starting from hematoporphyrin-IX dimethyl ester 1, a series of isomerically pure so-called benzoporphyrin derivatives (BPDs) 20, 23-25, 27, 28, 31-33, 35-37, 39, 40, 42, 44 and 45 have been synthesized. The bis-porphyrins 46 and 47 with carbon-carbon linkages were also prepared by treating 3- and 8-(1-hydroxyethyl) benzoporphyrin derivatives 24 and 32 with triflic acid. In preliminary in vivo studies, the hexyl ether derivatives 27, 35, 40 and 45 (as diastereoisomeric mixtures) appear to have better photosensitizing efficacy than the benzoporphyrin derivative monocarboxylic acid (BPD-MA; mixture of 21 and 22). Under similar doses and treatment conditions. other BPDs 23, 25, 26, 31, 33 and 34, along with bis-porphyrins 46 and 47 did not show any significant tumourcidal activity. The structures of the ring 'A' modified BPD isomers 20 (cis) and 36 (trans) were confirmed by single crystal X-ray studies.
引用
收藏
页码:961 / 969
页数:9
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