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A series of new 1,2-dihydro and 1,2,3,4-tetrahydroquinolines, synthesized from the corresponding propargylaniline intermediates, have been developed as antioxidants for the potential treatment of pathologies implicating central oxidative stress.

Stereospecific synthesis of cis and trans 3-substituted vinyl-gamma-aminobutyric acid analogs were obtained by either a Claisen rearrangement or a Wittig reaction from common diene precursors.

Several unsaturated thioacetic acids were synthesized as potential mechanism-based inhibitors of peptidyglycine α-hydroxylating monooxygenase (PHM) prepared from horse serum. Trans-styrylthioacetic acid produced potent time-dependent inhibition of PHM. Potential mechanisms are proposed to explain PHM inactivation by unsaturated thioacetic acids.

The synthesis, phosphorylation by guanylate kinase, anti HIV-1 and anti-herpesvirus activity of two acyclic dienyl phosphonate derivatives of guanine are described. (E)-9-(5-phosphono-3-methylene-4-pentenyl)guanine (4) was identified as an excellent substrate of guanylate kinase and a significant inhibitor of HIV-1 replication.

The synthesis, anti-HIV-1 and anti-herpesvirus activities of new rigid acyclonucleotide analogs are described. 9-[2-methylidene-3-(phosphonomethoxy)propyl]guanine 1a exhibits in vitro anti-HIV-1 activity similar to that of the antiviral agent 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA). Compound 1a is 9-fold less toxic to human T-lymphoid cells MT-4 than PMEA.

The synthesis and the reverse transcriptase inhibitory activity of new 5'-0-mono,di-and trifluoromethylphosphonate derivatives of nucleosides and 2'-deoxynucleosides are described.