166751-67-3Relevant academic research and scientific papers
Stereoselective synthesis of furo[2,3-c]pyridine pyrimidine thioethers, a new class of potent HIV-1 non-nucleoside reverse transcriptase inhibitors
Wishka, Donn G.,Graber, David R.,Seest, Eric P.,Dolak, Lester A.,Han, Fusen,Watt, William,Morris, Joel
, p. 7851 - 7859 (1998)
An efficient stereoselective total synthesis of the furo[2,3-c]pyridine thiopyrimidine HIV-1 reverse transcriptase inhibitors, PNU-142721 and PNU- 109886, has been developed. A convergent approach was utilized, providing direct access to the desired (S)-configuration of the molecule by making use of the alkylation of 4-amino-6-chloro-2-thiopyrimidine with the appropriate (R)-1-chloroethyl furo[2,3-c]pyridine intermediates. The successful preparation makes use of an efficient enzymatic kinetic resolution of the key 1-hydroxyethyl furo[2,3-c]pyridine intermediates to establish stereochemical control of the respective stereogenic centers. In addition, a workable asymmetric reduction strategy was developed for the synthesis of PNU-109886. Prudent reagent selection for the chlorination required for the final coupling reactions allowed for maintenance of the stereochemical integrity of the target compounds. Structural assignment of the absolute configuration of PNU-142721 and PNU-109886 as the (S)-enantiomer was confirmed by X-ray crystallographic analysis.
Pyrimidine-thioalkyl and alkylether compounds
-
Page 13, (2010/11/29)
The subject invention relates to pyrimidine-thioalkyl and alkylether compounds of Formula I and pyrimidine-thioalkyl and alkylethers of Formula IA, namely the compounds of Formula I whereR4 is selected from the group consisting of -H or -NRsub
Pyrimidine thioethers: A novel class of HIV-1 reverse transcriptase inhibitors with activity against BHAP-resistant HIV
Nugent, Richard A.,Schlachter, Stephen T.,Murphy, Michael J.,Cleek, Gary J.,Poel, Toni J.,Wishka, Donn G.,Graber, David R.,Yagi, Yoshihiko,Keiser, Barbara J.,Olmsted, Robert A.,Kopta, Laurie A.,Swaney, Steven M.,Poppe, Susan M.,Morris, Joel,Tarpley, W. Gary,Thomas, Richard C.
, p. 3793 - 3803 (2007/10/03)
A series of pyrimidine thioethers was synthesized and evaluated for inhibitory properties against wild-type HIV-1 reverse transcriptase (RT) and an RT carrying the resistance-conferring mutation P236L. Modifications of both the pyrimidine and the function
