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 | Zendy

Nagai Shinichi | Zendy; Ueda Taisei | Zendy; Sakakibara Hiroyuki | Zendy; Nagatsu Akito | Zendy; Murakami Nobutoshi | Zendy; Sakakibara Jinsaku | Zendy

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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.

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