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Synthesis and biological evaluation of structural variants of carbazoquinocin C
Author(s) -
Aygün Alparslan,
Pindur Ulf
Publication year - 2003
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.5570400303
Subject(s) - chemistry , oxalyl chloride , carbazole , radical , lipoxygenase , stereochemistry , alkaloid , oxidative phosphorylation , combinatorial chemistry , biochemistry , enzyme , organic chemistry
Some new structural variants of the alkaloid carbazoquinocin C were synthesized in a few steps with good to excellent yields. The key step comprises a cyclisation reaction of appropriate 2‐vinylindoles with oxalyl chloride. The carbazole‐3,4‐quinones are able to trap oxygen‐centred radicals. In some biological/biochemical assays some of these compounds exhibit extraordinary results including inhibition of cyclooxygenase‐1 and 5‐lipoxygenase in the μM‐range. Moreover some of the carbazoquinocin C‐variants inhibit significant oxidative damage of cellular DNA in nM‐range.