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Antineoplastic anthraquinones. II . Design and synthesis of 1,2‐Heteroannelated anthraquinones
Author(s) -
Chang Pong,
Chen ChiaFu
Publication year - 1996
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570330227
Subject(s) - anthraquinones , chemistry , quinoxaline , imidazole , stereochemistry , cytotoxic t cell , organic chemistry , biochemistry , in vitro , biology , botany
Based on the “2‐phenyinaphthalene‐type” structural pattern hypothesis, a number of heterocycle‐fused anthraquinones were designed by taking morindaparvin‐A ( 2a ) as the lead structure. The compounds we synthesized and tested for antineoplastic activity include 1,2‐alkylenedioxyanthraquinone, naphtho [2,3‐ f ]‐quinoxaline‐7,12‐dione, anthra[1,2‐ d ]imidazole‐6,11‐dione and naphtho[2,3‐ f ]quinoxaline‐7,12‐dione derivatives. Most of the synthesized anthraquinones possessed various degrees of anticancer activity. One of these compounds, 2‐chloromethyl‐1 H ‐anthra[1,2‐ d ]imidazole‐6,11‐dione ( 4b ), exhibited cytotoxic activity against all tested human carcinoma cell lines.