Novel cyclourethane-derived HIV protease inhibitors: a ring-closing olefin metathesis based strategy.
A series of novel macrocyclic urethanes incorporating a (R)-hydroxyethylamine isostere was designed and synthesized. Ring size and substituent efffects have been investigated. Cyclourethanes containing 14- to 16-membered rings exhibited low nanomolar inhibitory potencies against HIV-1 protease.
Ghosh
Arun K
AK
Department of Chemistry, University of Illinois at Chicago, 60607, USA. arunghos@uic.edu
Swanson
Lisa M
LM
Liu
Chunfeng
C
Hussain
Khaja Azhar
KA
Cho
Hanna
H
Walters
D Eric
DE
Holland
Louis
L
Buthod
Jim
J
D000475:Alkenes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D015195:Drug Design; D017320:HIV Protease Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D007700:Kinetics; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014520:Urethane / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D000475:Alkenes; D000588:Amines; D017320:HIV Protease Inhibitors; D014520:Urethane