Synthesis and progesterone receptor antagonist activities of 6-aryl benzimidazolones and benzothiazolones.
Novel 6-aryl benzimidazolones and benzothiazolones were prepared and examined as bioisosteres of the recently reported 6-aryl dihydroquinolines (1) for progesterone receptor (PR) antagonist activities. PR antagonist activities increased when compounds 9c-f possessed a more lipophilic group at position-1 and pendent aryl moiety para to NH moiety. Furthermore, conversion of carbonyl moiety of 9e,f to the thio-carbonyl led to benzoimidazolethiones 15a,b with significantly improved potency and binding affinity.
Zhang
P
P
Medicinal Chemistry I, Chemical Sciences, Wyeth-Ayerst Research, Radnor, PA 19087, USA. zhang@war.wyeth.com
Terefenko
E A
EA
Wrobel
J
J
Zhang
Z
Z
Zhu
Y
Y
Cohen
J
J
Marschke
K B
KB
Mais
D
D
D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011980:Receptors, Progesterone / Q000037:antagonists & inhibitors*; D013329:Structure-Activity Relationship
D001562:Benzimidazoles; D011980:Receptors, Progesterone; C014353:benzimidazolone