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Indolizine 1-sulfonates as potent inhibitors of 15-lipoxygenase from soybeans.

Teklu S, Gundersen LL, Larsen T, Malterud KE, Rise F

Department of Chemistry, University of Oslo, PO Box 1033, Blindern, N-0315 Oslo, Norway.

A number of indolizine 1-sulfonates have been prepared by cyclization of cyclopropenones with pyridines followed by trapping of the intermediate 1-indolizinol with a sulfonyl halide, and examined as inhibitors of 15-lipoxygenase (15-LO). The compounds display IC(50) values between 15 and 42 microM; all are more active than the well-known 15-LO inhibitor quercetin (IC(50) 51 microM). A wide variety of substituents are well tolerated. The enzyme inhibition was not affected by preincubation or the presence of a detergent and no significant particle formation was observed. Hence, inhibition from aggregates of indolizines, promiscuous inhibition, is highly unlikely.

Published 5 April 2005 in Bioorg Med Chem, 13(9): 3127-39.
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