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Discovery of GS-9131: Design, synthesis and optimization of amidate prodrugs of the novel nucleoside phosphonate HIV reverse transcriptase (RT) inhibitor GS-9148.
Mackman RL, Ray AS, Hui HC, Zhang L, Birkus G, Boojamra CG, Desai MC, Douglas JL, Gao Y, Grant D, Laflamme G, Lin KY, Markevitch DY, Mishra R, McDermott M, Pakdaman R, Petrakovsky OV, Vela JE, Cihlar T. Mackman RL, et al. Among authors: zhang l. Bioorg Med Chem. 2010 May 15;18(10):3606-17. doi: 10.1016/j.bmc.2010.03.041. Epub 2010 Mar 27. Bioorg Med Chem. 2010. PMID: 20409721
Synthesis, anti-HIV activity, and resistance profile of thymidine phosphonomethoxy nucleosides and their bis-isopropyloxymethylcarbonyl (bisPOC) prodrugs.
Mackman RL, Zhang L, Prasad V, Boojamra CG, Douglas J, Grant D, Hui H, Kim CU, Laflamme G, Parrish J, Stoycheva AD, Swaminathan S, Wang K, Cihlar T. Mackman RL, et al. Among authors: zhang l. Bioorg Med Chem. 2007 Aug 15;15(16):5519-28. doi: 10.1016/j.bmc.2007.05.047. Epub 2007 May 25. Bioorg Med Chem. 2007. PMID: 17562366
Design and profiling of GS-9148, a novel nucleotide analog active against nucleoside-resistant variants of human immunodeficiency virus type 1, and its orally bioavailable phosphonoamidate prodrug, GS-9131.
Cihlar T, Ray AS, Boojamra CG, Zhang L, Hui H, Laflamme G, Vela JE, Grant D, Chen J, Myrick F, White KL, Gao Y, Lin KY, Douglas JL, Parkin NT, Carey A, Pakdaman R, Mackman RL. Cihlar T, et al. Among authors: zhang l. Antimicrob Agents Chemother. 2008 Feb;52(2):655-65. doi: 10.1128/AAC.01215-07. Epub 2007 Dec 3. Antimicrob Agents Chemother. 2008. PMID: 18056282 Free PMC article.
Inside cells, GS-9131 is readily hydrolyzed to GS-9148, which is further phosphorylated to its active diphosphate metabolite (A. S. Ray, J. E. Vela, C. G. Boojamra, L. Zhang, H. Hui, C. Callebaut, K. Stray, K.-Y. Lin, Y. Gao, R. L. Mackman, and T. Cihlar, Ant …
Inside cells, GS-9131 is readily hydrolyzed to GS-9148, which is further phosphorylated to its active diphosphate metabolite (A. S. Ray, J. …
Synthesis and anti-HIV activity of cyclic pyrimidine phosphonomethoxy nucleosides and their prodrugs: a comparison of phosphonates and corresponding nucleosides.
Mackman RL, Zhang L, Prasad V, Boojamra CG, Chen J, Douglas J, Grant D, Laflamme G, Hui H, Kim CU, Parrish J, Stoycheva AD, Swaminathan S, Wang K, Cihlar T. Mackman RL, et al. Among authors: zhang l. Nucleosides Nucleotides Nucleic Acids. 2007;26(6-7):573-7. doi: 10.1080/15257770701490126. Nucleosides Nucleotides Nucleic Acids. 2007. PMID: 18066858
Discovery of an oral respiratory syncytial virus (RSV) fusion inhibitor (GS-5806) and clinical proof of concept in a human RSV challenge study.
Mackman RL, Sangi M, Sperandio D, Parrish JP, Eisenberg E, Perron M, Hui H, Zhang L, Siegel D, Yang H, Saunders O, Boojamra C, Lee G, Samuel D, Babaoglu K, Carey A, Gilbert BE, Piedra PA, Strickley R, Iwata Q, Hayes J, Stray K, Kinkade A, Theodore D, Jordan R, Desai M, Cihlar T. Mackman RL, et al. Among authors: zhang l. J Med Chem. 2015 Feb 26;58(4):1630-43. doi: 10.1021/jm5017768. Epub 2015 Jan 27. J Med Chem. 2015. PMID: 25574686 Clinical Trial.
Discovery and Synthesis of a Phosphoramidate Prodrug of a Pyrrolo[2,1-f][triazin-4-amino] Adenine C-Nucleoside (GS-5734) for the Treatment of Ebola and Emerging Viruses.
Siegel D, Hui HC, Doerffler E, Clarke MO, Chun K, Zhang L, Neville S, Carra E, Lew W, Ross B, Wang Q, Wolfe L, Jordan R, Soloveva V, Knox J, Perry J, Perron M, Stray KM, Barauskas O, Feng JY, Xu Y, Lee G, Rheingold AL, Ray AS, Bannister R, Strickley R, Swaminathan S, Lee WA, Bavari S, Cihlar T, Lo MK, Warren TK, Mackman RL. Siegel D, et al. Among authors: zhang l. J Med Chem. 2017 Mar 9;60(5):1648-1661. doi: 10.1021/acs.jmedchem.6b01594. Epub 2017 Feb 14. J Med Chem. 2017. PMID: 28124907
Discovery of a 2'-fluoro-2'-C-methyl C-nucleotide HCV polymerase inhibitor and a phosphoramidate prodrug with favorable properties.
Kirschberg TA, Metobo S, Clarke MO, Aktoudianakis V, Babusis D, Barauskas O, Birkus G, Butler T, Byun D, Chin G, Doerffler E, Edwards TE, Fenaux M, Lee R, Lew W, Mish MR, Murakami E, Park Y, Squires NH, Tirunagari N, Wang T, Whitcomb M, Xu J, Yang H, Ye H, Zhang L, Appleby TC, Feng JY, Ray AS, Cho A, Kim CU. Kirschberg TA, et al. Among authors: zhang l. Bioorg Med Chem Lett. 2017 Apr 15;27(8):1840-1847. doi: 10.1016/j.bmcl.2017.02.037. Epub 2017 Feb 20. Bioorg Med Chem Lett. 2017. PMID: 28274633
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