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Bioorg Med Chem Lett. 2013 Dec 15;23(24):6640-4. doi: 10.1016/j.bmcl.2013.10.052. Epub 2013 Oct 31.

Function-regulating pharmacophores in a sulfonamide class of glucocorticoid receptor agonists.

Author information

1
Department of Medicinal Chemistry, Boehringer Ingelheim Pharmaceuticals Inc., 900 Ridgebury Road, PO Box 368, Ridgefield, CT 06877-0368, USA. Electronic address: dkuzmich@aol.com.

Abstract

A class of α-methyltryptamine sulfonamide glucocorticoid receptor (GR) modulators was optimized for agonist activity. The design of ligands was aided by molecular modeling, and key function-regulating pharmacophoric points were identified that are critical in achieving the desired agonist effect in cell based assays. Compound 27 was profiled in vitro and in vivo in models of inflammation. Analogs could be rapidly prepared in a parallel approach from aziridine building blocks.

KEYWORDS:

Arylsulfonamide; Collagen induced arthritis; Glucocorticoid receptor; Glucocorticoids; Inflammation; Mineralocorticoid receptor; Nuclear hormone receptor; Progesterone receptor

PMID:
24215891
DOI:
10.1016/j.bmcl.2013.10.052
[Indexed for MEDLINE]

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