Bioorganic and Medicinal Chemistry Letters p. 3600 - 3603 (2005)
Update date:2022-08-05
Topics:
Terefenko, Eugene A.
Kern, Jeffrey
Fensome, Andrew
Wrobel, Jay
Zhu, Yuan
Cohen, Jeffrey
Winneker, Richard
Zhang, Zhiming
Zhang, Puwen
We have previously reported that the aryl substituted benzimidazolones, benzoxazinones, and oxindoles (e.g., 1-3) are progesterone receptor (PR) antagonists and have recently disclosed that the nature of 5- and 6-aryl moieties played a critical role in PR functional activity in the oxindole and benzoxazinone templates. For example, replacing the phenyl group of PR antagonists 2 and 3 with a 5′-cyanopyrrol-2′-yl moiety switched their functional activity to PR agonist activity (2a and 3a). These findings prompted us to examine if there is a similar effect of the 6-aryl moieties on the PR functional activity for the benzimidazolone template. Numerous analogs, such as 5, showed potent PR antagonist activity with about a 10-fold increase in potency as compared to those reported earlier in the same series. More interestingly, pyrrole-containing benzimidazolones 24-27 remained as PR antagonists in contrast to the PR agonist activity switch for oxindole and benzoxazinone scaffolds when a 5′-cyanopyrrol-2′-yl group was installed as a pendant aryl group.
View Morejiangsu senxuan pharmaceutical and chemical co.,ltd
Contact:86-523-87982810
Address:hongqiao industrial zone,taixing,jiangsu china
Shandong Zhongcheng Barium Salt Co., Ltd
Contact:+86-15725732638
Address:No.29 baoxi road, hi-tech zone, zibo, shandong
JIANGXI ZHANGFENG CHEMICAL CO., LTD.
Contact:+86-0799-3413066
Address:Xiyuan village, Xiabu Town, Xiangdong District
Zhejiang Allied Chemical Co.,Ltd
Contact:18967038207
Address:Area A-30, High-tech Industrial Park, Quzhou, Zhejiang, China.
Disynthesis Chemical Technology Co. Ltd.
Contact:+86-571-88194596
Address:Dengyun road 380, Gongshu district, Hangzhou city, China
Doi:10.1021/ol051126+
(2005)Doi:10.1016/j.farmac.2004.07.014
(2004)Doi:10.1021/jo00164a018
(1983)Doi:10.1002/adsc.202100236
(2021)Doi:10.1039/c9sc05532k
(2020)Doi:10.1016/S0040-4039(00)81587-7
(1983)