Novel pyrrole-containing progesterone receptor modulators.

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Collins MA, Hudak V, Bender R, Fensome A, Zhang P, Miller L, Winneker RC, Zhang Z, Zhu Y, Cohen J, Unwalla RJ, Wrobel J

Novel pyrrole-containing progesterone receptor modulators.

Bioorg Med Chem Lett. 2004 May 3;14(9):2185-9.

PubMed ID

15081005 [ View in PubMed

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Abstract

A series of 1,4-dihydro-2H-[d][3,1]-benzoxazin-2-one and 1,3-dihydro-[3H]-indol-2-one containing 6- or 5-, respectively, appended substituted pyrrole moieties were synthesized and evaluated for their ability to modulate the activity of the progesterone receptor (PR). Key structural changes to the pyrrole moieties of these molecules were shown to have a predictive influence as to whether the compounds behaved as PR agonists or antagonists. Compounds with the 5(')-cyano-2(')-pyrrole moiety (e.g., 32, 33, and 38) were shown to be potent PR agonists (EC(50)'s of 1.1, 1.8, and 2.8 nM, respectively). Compounds with the 5(')-nitro-2(')-pyrrole moiety (e.g., 34 and 36) were shown to be PR antagonists (IC(50)'s of 180 and 36 nM, respectively).

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Medroxyprogesterone acetate	Progesterone receptor	EC 50 (nM)	0.5	N/A	N/A	Details