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Title: Synthesis and biochemical evaluation of benzyl propargyl ethers as inhibitors of 5-lipoxygenase
Authors: Barhate, N B
Reddy, Madhava C
Reddy, P Srinivas
Wakharkar, R D
Reddanna, P
Issue Date: Aug-2002
Publisher: NISCAIR-CSIR, India
Abstract: A series of benzyl propargyl ethers were synthesized and tested as inhibitors of 5- lipoxygenase, the key enzyme involved in leukotriene biosynthesis. Among these, optimum activity was displayed by 1-(2-heptynyloxymethyl) benzene 12 (IC50 1.2 µM). Addition of carboxyl group at the end of the alkyl side chain attached to the acetylenic group abolished the inhibition. Selective reduction of the acetylenic group to cis or trails double bond reduced the inhibitory potential,  the cis isomer 24 showing more than 20-fold higher inhibition than the trans isomer 25. Introduction of sulphur in place of oxygen in th e alkyl side chain attached to the (carboxyalkyl) benzyl group also reduced the inhibition. The IC50value of 12, towards rabbit reticulocyte 15-LOX is > 50 fold higher than that of 5-LOX. These results indicate that compound 12 is a specific inhibitor of 5-LOX.
Page(s): 264-273
ISSN: 0975-0959 (Online); 0301-1208 (Print)
Appears in Collections:IJBB Vol.39(4) [August 2002]

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