132178-47-3Relevant academic research and scientific papers
Synthesis, anti-HIV activity, and resistance profiles of ribose modified nucleoside phosphonates
Mackman, Richard L.,Boojamra, Constantine G.,Prasad, Vidya,Zhang, Lijun,Lin, Kuei-Ying,Petrakovsky, Oleg,Babusis, Darius,Chen, James,Douglas, Janet,Grant, Deborah,Hui, Hon C.,Kim, Choung U.,Markevitch, David Y.,Vela, Jennifer,Ray, Adrian,Cihlar, Tomas
, p. 6785 - 6789 (2008/09/18)
A series of nucleoside phosphonate reverse transcriptase (RT) inhibitors have been synthesized and their anti-HIV activity and resistance profiles evaluated. The most potent analog [5-(6-amino-purin-9-yl)-2,5-dihydro-furan-2-yloxymethyl]-phosphonic acid (d4AP) demonstrated a HIV EC50 = 2.1 μM, and the most favorable resistance profile against HIV-1 variants with K65R, M184V or multiple thymidine analog mutations in RT.
Regiospecific and Highly Stereoselective Electrophilic Addition to Furanoid Glycals: Synthesis of Phosphonate Nucleotide Analogues with Potent Activity against HIV
Kim, Choung Un,Luh, Bing Y.,Martin, John C.
, p. 2642 - 2647 (2007/10/02)
Regiospecific and highly stereoselective electrophilic addition to furanoid glycals has been used as a key step in the synthesis of phosphonate isosteres of nucleoside monophosphates.Using this methodology, phosphonate analogues of 1 (ddA), 4 (d4T), and 5 (d4A) monophosphates have been prepared.Present studies have also led to the development of a scheme for the synthesis of the phosphonate isostere of adenosine monophosphate.Despite the acetal structure, phosphonate derivatives 27 and 28 were substantially more acid stable than the corresponding nucleosides 1 and 5 with respect to glycosidic bond cleavage.The phosphonates 22 and 27 exhibited a potent antiretroviral activity comparable to that of 4 (d4T).
