Abstract
Various carbamate analogs of lysophospholipids, N-alkyl-and alkenylcarbamoyl phospholipids (ACPLs), were synthesized and their antimicrobial properties were examined. The ACPLs studied differed in certain aspects of their chemical structure : the polar-head base, the aliphatic nonpolar tail attached to the carbamate nitrogen and the molecular backbone, e.g., 2-O-methylglycerol and 1, 3-propanediol. In contrast to lysolecithin and lecithin, the majority of the ACPLs showed inhibitory activities against Tetrahymena pyriformis (protozoan) and a range of fungi. In the series of ACPLs studied, the maximal inhibitory activities were observed with 2-O-methyl-1-O-(N-tetradecyl) carbamoylglycero-3-phosphocholine (3-C14-A) and its 2-demethoxy compound (4-C14-A). In comparison with clotrimazole, these compounds showed more potent activities against T. pyriformis, and comparable or lower activities against human pathogenic and phytopathogenic fungi. The relationships between structure and antimicrobial activity are discussed.
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