to the total synthesis of (−)-Abacavir ..

Synthesis of carbovir and abacavir from a carbocyclic precursor

Synthesis of Carbovir and Abacavir from a Carbocyclic Precursor

Abacavir is a carbocyclic synthetic nucleoside analogue. Abacavir is converted by cellular enzymes to the active metabolite, carbovir triphosphate (CBV-TP), an analogue of deoxyguanosine-5′-triphosphate (dGTP). CBV-TP inhibits the activity of HIV-1 reverse transcriptase (RT) both by competing with the natural substrate dGTP and by its incorporation into viral DNA.

Abacavir prodrugs: Microwave-assisted synthesis and …

Synthesis and characterization of potent Abacavir impurities

Abacavir (ABC) is clinically associated with hypersensitivity reactions, risk for cardiovascular disease, etc. A possible way to minimize side effects is by modifying chemical structure. Three esters of ABC containing amino acid (glycine) and dipeptide esters (glycyl-glycine) were synthesized and their activity on HIV-1 III B replication in MT-4 cells was evaluated. One of the newly synthesized esters—Gly-ABC—demonstrates low-cytotoxicity and high-anti-HIV-1 activity in MT-4 cells, as well as low-mitochondrial toxicity and high-genetic barrier to resistance.

Ail efficient synthesis of the highly potent anti-HIV carbocyclic nucleosides (-)-carbovir and (-)-abacavir has been accomplished from D-(-)-ribose using a rhodium(I)-catalysed tandem hydrosilylation-intramolecular aldol strategy to access it key intermediate.