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Section 1: Synthesis, Structure, Stereochemistry and Reactivity of Organophosphorus Compounds

Design and Synthesis of Organophosphorus Compounds with Antiviral and Other Bioactivities

C.E. Mckenna Department of Chemistry, University of Southern California, Los Angeles, CA, 90089-0744, U.S.A.

T.-G. Ye Department of Chemistry, University of Southern California, Los Angeles, CA, 90089-0744, U.S.A.; Wenzhou Institute of Pesticide Research, Huiqiaopu, Wenzhou, Zhejiang, China

J. N. Levy Department of Chemistry, University of Southern California, Los Angeles, CA, 90089-0744, U.S.A.; University of California Universitywide Task Force on AIDS Postdoctoral Fellow

P. Pham Department of Chemistry, University of Southern California, Los Angeles, CA, 90089-0744, U.S.A.

T. Wen Department of Chemistry, University of Southern California, Los Angeles, CA, 90089-0744, U.S.A.

J.-P. Bongartz Department of Chemistry, University of Southern California, Los Angeles, CA, 90089-0744, U.S.A.

M. C. Starnes Department of Pharmacology and Medicine, School of Medicine, University of North Carolina, Chapel Hill, NC, 27514, U.S.A.

Y.-C. Cheng Department of Pharmacology and Medicine, School of Medicine, University of North Carolina, Chapel Hill, NC, 27514, U.S.A.; Department of Pharmacology, School of Medicine, Yale University, New Haven, CT, 06510, U.S.A.

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Abstract

Investigations of phosphonates and related biophosphate analogues as inhibitors of viral nucleic acid polymerases are summarized. General syntheses of α-halo phosphonoacetic acid (PAA) and methanediphosphonic acid (MDP) derivatives have been extended to preparation of seven α-halo phenyl (phosphonomethyl) phosphinates (PhMpP). Two phosphonates containing potentially reactive α-keto groups, oxophosphonoacetate (phosphonoglyoxalate, COPAA) and oxomethanediphosphonate (carbonyldiphosphonate, COMDP) are discussed. A convenient, two-step synthesis of trisodium thiophosphonoformate (TPFA) from trimethyl phosphonoformate (Me₃PFA) [via Me₃TPFA) is presented. TPFA selectively inhibits HIV-1 reverse transcriptase (RT) relative to both human DNA polymerase α (pol α) and four herpesvirus DNA polymerases. The significance of membrane Na⁺/Pi cotransport inhibition by phosphonates is briefly addressed.

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Design and Synthesis of Organophosphorus Compounds with Antiviral and Other Bioactivities

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Design and Synthesis of Organophosphorus Compounds with Antiviral and Other Bioactivities

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