Irreversible enzyme inhibitors. Inhibitors of guinea pig complement derived by quaternization of substituted pyridines with benzyl halides
- 1 September 1976
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 19 (9) , 1079-1088
- https://doi.org/10.1021/jm00231a001
Abstract
A series of 83 compounds derived from hydrocarbon-substituted pyridines by quaternization with PhCH2Br usually containing a 2-SO2F or 6-Cl-2-SO2F group was synthesized and evaluated as inhibitors of guinea pig complement [C] and in most cases its C.hivin.1 component [activated 1st C component]. The most active compounds were 3-(4-phenylphenylbutyl)-N-(6-chloro-2-fluorosulfonylbenzyl)pyridinium bromide and 3-(4-phenylphenylbutyl)-N-(2-fluorosulfonylbenzyl)pyridinium bromide, each showing 50% inhibition at 7.8 .mu.M. The most effective irreversible inhibitor of the C.hivin.1 component was N-(6-chloro-2-fluorosulfonylbenzyl)-5,6-benzoquinolinium bromide, which showed 50% inhibition at 4 .mu.M.This publication has 4 references indexed in Scilit:
- Complement in Human DiseaseAnnual Review of Medicine, 1968
- Irreversible Enzyme Inhibitors. CVII.1Proteolytic Enzymes. II.2Bulk Tolerance within Chymotrypsin-Inhibitor ComplexesJournal of Medicinal Chemistry, 1967
- Irreversible Enzyme Inhibitors. CVI.1 Proteolytic Enzymes. I. Bulk Tolerances in Trypsin-Inhibitor Complexes2Journal of Medicinal Chemistry, 1967
- The Correlation of Biological Activity of Plant Growth Regulators and Chloromycetin Derivatives with Hammett Constants and Partition CoefficientsJournal of the American Chemical Society, 1963