S-triazolyl α-mercapto acetanilides as inhibitors of HIV reverse transcriptase
View Patent ↗A series of S-triazolyl α-mercaptoacetanilides having general structure (1) are provided, where Q is CO 2 H, CONR 2 , SO 3 H, or SO 2 NR 2 . The compounds inhibit several variants of the reverse transcriptase of HIV, and are useful in the treatment of HIV infections.
1. A compound of Formula A″
wherein
R 1 is C 1-3 alkyl, CF 3 , CHF 2 , CH 2 F, Cl, Br, NH 2 , or hydrogen;
R 2 is 4-Q-naphth-1-yl or 4-Q-phen-1-yl;
Q is C 2-5 alkyl;
W is S, O or an optionally substituted amine;
R 3 is C 1-3 alkyl, CF 3 , CHF 2 , CH 2 F, Cl, Br; and
R 4 is COR′ or S(O) 2 R′, wherein R′ is NH 2 or NH(alkyl).
2. The compound of claim 1 , where W is S.
3. The compound of claim 1 , wherein R 1 is other than H.
4. The compound of claim 1 , wherein Q is ethyl.
5. The compound of claim 1 , wherein R 3 is chloro or methyl.
6. The compound of claim 1 , which is
2-[5-bromo-4-(4-ethyl-naphthalen-1-yl)-4H-[1,2,4]triazol-3-ylsulfanyl]-N-(2-chloro-4-sulfamoyl-phenyl)-acetamide or
2-[5-bromo-4-(4-ethyl-naphthalen-1-yl)-4H-[1,2,4]triazol-3-ylsulfanyl]-N-(2-chloro-4-carbamoyl-phenyl)-acetamide.