10.1021/jm00108a021
The research evaluates a series of synthetic lipids containing a two- or three-carbon backbone substituted with a thio, oxy, or amidoalkyl functionality and either a phosphocholine or quaternary ammonium moiety as potential anti-HIV-1 agents. The most promising compound identified is rac-3-octadecanamido-2-etholrypropylphosphocholine (8), which exhibited an ICso for the inhibition of plaque formation of 0.16 pM, significantly lower than the ICw value determined for CEM-SS cell growth inhibition. Unlike AZT, these compounds appear to inhibit a late step in HIV replication involving virus assembly and infectious virus production. Key chemicals involved in the research include AZT as a reference compound, various phospholipid analogues such as ET-18-OMe, ET-18-OEt, and compound 8, as well as nonphosphorus-containing analogues like compounds 20, 22, and 27. The study also involved the synthesis of several compounds, including 2, 3, 17, 24, 26, and 37, using starting materials like 1,2-dimethylethylene phosphorochloridate (CEP-Cl), 2-(isopropylamino)ethanol, 2-(tert-butylamino)ethanol, and other reagents such as p-toluenesulfonyl chloride and dicyclohexylcarbodiimide (DCC).
