S-Triazolyl alpha-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 an aryl or heteroaryl moiety which can be further substituted with alkyl, cycloalkyl, aryl or heteroaryl moieties;
Q is C 3-5 cycloalkyl;
W is S, O, or an optionally substituted amine;
R 3 is C 1-3 alkyl, CF 3 , CHF 2 , CH 2 F, Cl or 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 , wherein R 2 is 4-Q-naphth-1-yl or 4-Q-phen-1-yl.
3. The compound of claim 1 , wherein R′ is NH 2 .
4. The compound of claim 3 , wherein Q is cyclopropyl.
5. The compound of claim 3 , wherein W is S.
6. The compound of claim 4 , wherein W is S.
7. The compound of claim 6 , wherein R 1 is other than hydrogen.
8. The compound of claim 7 , wherein R 1 is Br, R 2 is naphthyl, and R 3 is methyl or Cl.
9. The compound of claim 8 , which is
2-[5-bromo-4-(4-cyclopropyl-naphthalen-1-yl)-4H-[1,2,4]triazol-3-ylsulfanyl]-N-(2-chloro-4-sulfamoyl-phenyl)-acetamide or
2[5-bromo-4-(4-cyclopropyl-naphthalen-1-yl)-4H-[1,2,4]triazol-3-ylsulfanyl]-N-(2-chloro-4-carbamoyl-phenyl)-acetamide.
10. The compound of claim 8 , which is
2-[5-bromo-4-(4-cyclopropyl-naphthalen-1-yl)-4H-[1,2,4]triazol-3-ylsulfanyl]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide or
2[5-bromo-4-(4-cyclopropyl-naphthalen-1-yl)-4H-[1,2,4]triazol-3-ylsulfanyl]-N-(2-methyl-4-carbamoyl-phenyl)-acetamide.