Selective thromboxane synthetase inhibitors. 1. 1-[(Aryloxy)alkyl]-1H-imidazoles.
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Cross PE, Dickinson RP, Parry MJ, Randall MJ
Selective thromboxane synthetase inhibitors. 1. 1-[(Aryloxy)alkyl]-1H-imidazoles.
J Med Chem. 1985 Oct;28(10):1427-32.
- PubMed ID
- 3930740 [ View in PubMed]
- Abstract
1-(2-Phenoxyethyl)-1H-imidazole was found to be an inhibitor of thromboxane (TxA2) synthetase, but it also inhibited the adrenal cytochrome P-450 enzyme steroid 11 beta-hydroxylase. The preparation of a series of analogues is described, and activity against TxA2 synthetase, PGI2 synthetase, cyclooxygenase, and steroid 11 beta-hydroxylase is discussed. Potency against TxA2 synthetase was increased by introduction of a carboxyl group at a suitable distance from the imidazole ring. A distance of 8.1-8.8 A between N-1 of the imidazole and the carboxyl carbon was found to be optimal. Introduction of a carboxyl group also had the effect of reducing activity against steroid 11 beta-hydroxylase. The most potent and selective compound was found to be 4-[2-(1H-imidazol-1-yl) ethoxy]benzoic acid (14).
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- Binding Properties
Drug Target Property Measurement pH Temperature (°C) Dazoxiben Thromboxane-A synthase IC 50 (nM) 3 N/A N/A Details