title: Synthesis and progesterone receptor antagonist activities of 6-aryl benzimidazolones and benzothiazolones.
abstract: 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.
authors.affiliation: Medicinal Chemistry I, Chemical Sciences, Wyeth-Ayerst Research, Radnor, PA 19087, USA. zhang@war.wyeth.com
authors.forename: P
authors.initials: P
authors.lastname: Zhang
authors.forename: E A
authors.initials: EA
authors.lastname: Terefenko
authors.forename: J
authors.initials: J
authors.lastname: Wrobel
authors.forename: Z
authors.initials: Z
authors.lastname: Zhang
authors.forename: Y
authors.initials: Y
authors.lastname: Zhu
authors.forename: J
authors.initials: J
authors.lastname: Cohen
authors.forename: K B
authors.initials: KB
authors.lastname: Marschke
authors.forename: D
authors.initials: D
authors.lastname: Mais
mesh_terms: D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011980:Receptors, Progesterone / Q000037:antagonists & inhibitors*; D013329:Structure-Activity Relationship
chemical_list: D001562:Benzimidazoles; D011980:Receptors, Progesterone; C014353:benzimidazolone