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Studies on the chemical transformations of rotenoids. 5 . Synthesis and cytotoxicity of 1,3‐diazepino[5,6‐ b ]benzofuran and pyridazino[4,5‐ b ]benzofurans fused with thiazole, imidazole and pyrimidine
Author(s) -
Nagai Shinichi,
Ueda Taisei,
Sakakibara Hiroyuki,
Nagatsu Akito,
Murakami Nobutoshi,
Sakakibara Jinsaku
Publication year - 1998
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.5570350316
Subject(s) - chemistry , benzofuran , thiazole , sodium methoxide , imidazole , cytotoxicity , potassium carbonate , stereochemistry , thiadiazoles , pyrimidine , medicinal chemistry , organic chemistry , biochemistry , in vitro , catalysis
Novel benzofuro[2,3‐ d ]pyridazinium chlorides fused with thiazole 5a , imidazole 5b‐c and pyrimidine 5d‐f were prepared starting from 4‐chloropyridazino[4,5‐ b ]benzofuran 3a . Treatment of 5b, 5d and 5e with 10% potassium carbonate solution provided the corresponding free bases 6a‐c . Ring closure of methyl rotenononate 1b with amidines proceeded in the presence of sodium methoxide to give 1,3‐diazepino[5,6‐ b ]benzofuran‐5‐ones 7a‐c . Compound 5d showed cytotoxicity against P388 and L1210 leukemia cells.