Synthesis and progesterone receptor antagonist activities of 6-aryl benzimidazolones and benzothiazolones

Novel 6-aryl benzimidazolones and benzothiazolones were prepared and examin ed as bioisosteres of the recently reported 6-aryl dihydroquinolines (1) fo r progesterone receptor (PR) antagonist activities. PR antagonist activitie s increased when compounds 9c-f possessed a more lipophilic group at positi on-1 and pendent aryl moiety para to NH moiety. Furthermore, conversion of carbonyl moiety of 9e,f to the thio-carbonyl led to benzoimidazolethiones 1 5a,b with significantly improved potency and binding affinity. (C) 2001 Els evier Science Ltd. All rights reserved.