Use of Lawesson's reagent in organic syntheses.

The synthesis of the first series of a new class of nucleoside phosphonate analogues is described. Addition of a carboxyl group at the α position of carbocyclic nucleoside phosphonate analogues leads to a novel class of potent HIV reverse transcriptase (RT) inhibitors, α-carboxy nucleoside phosphonates (α-CNPs). Key steps in the synthesis of the compounds are Rh-catalyzed O–H insertion and Pd-catalyzed allylation reactions. In cell-free assays, the final products are markedly inhibitory against HIV RT and do not require phosphorylation to exhibit anti-RT activity, which indicates that the α-carboxyphosphonate function is efficiently recognized by HIV RT as a triphosphate entity, an unprecedented property of nucleoside monophosph(on)ates.

Design and synthesis of α-carboxy nucleoside phosphonate analogues and evaluation as HIV-1 reverse transcriptase-targeting agents.

2,4,6-Tris(p-methoxyphenyl)-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trisulphide 2, obtained from trimethyl phosphonoformate ester 3 and Lawesson's reagent 1 in acetonitrile, has been structurally characterized by X-ray diffraction.

X-Ray crystal structure of 2,4,6-tris(p-methoxyphenyl)-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trisulphide, a co-product in P O → P S thionation with Lawesson's reagent

Synthesis of oligodeoxyribonucleoside phosphorothioates using Lawesson's Reagent for the Sulfur Transfer Step

A new approach, ketone derivatization, for introducing desired functionality into the α-keto pyrophosphate analogues oxophosphonoacetic acid (COPAA) and oxomethanediphosphonic acid (COMDP) is exemplified in the synthesis of several COPAA and COMDP hydrazones with specific functional groups. The preparation of tetraalkyl COMDP esters is also described. Inhibition of HIV-1 reverse transcriptase (isolated enzyme) and of p24 production by HIV-1 (virus-infected H9 cells) by hydrazone derivatives of COPAA and COMDP is briefly discussed.

Synthesis and HIV-1 Reverse Transcriptase Inhibition Activity of Functionalized Pyrophosphate Analogues

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.

Design and Synthesis of Organophosphorus Compounds with Antiviral and Other Bioactivities

Sodium Thiophosphonoformate, A Selective HIV RT Inhibitor

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Design and Synthesis of Organophosphorus Compounds with Antiviral and Other Bioactivities

Design and Synthesis of Organophosphorus Compounds with Antiviral and Other Bioactivities

Sodium Thiophosphonoformate, A Selective HIV RT Inhibitor