Synthesis and SAR of tetrahydropyrrolo[1,2-b][1,2,5]thiadiazol-2(3H)-one 1,1-dioxide analogues as highly potent selective androgen receptor modulators

Mark C Manfredi; Yingzhi Bi; Alexandra A Nirschl; James C Sutton; Ramakrishna Seethala; Rajasree Golla; Blake C Beehler; Paul G Sleph; Gary J Grover; Jacek Ostrowski; Lawrence G Hamann

doi:10.1016/j.bmcl.2007.06.007

Synthesis and SAR of tetrahydropyrrolo[1,2-b][1,2,5]thiadiazol-2(3H)-one 1,1-dioxide analogues as highly potent selective androgen receptor modulators

Bioorg Med Chem Lett. 2007 Aug 15;17(16):4487-90. doi: 10.1016/j.bmcl.2007.06.007. Epub 2007 Jun 6.

Authors

Mark C Manfredi¹, Yingzhi Bi, Alexandra A Nirschl, James C Sutton, Ramakrishna Seethala, Rajasree Golla, Blake C Beehler, Paul G Sleph, Gary J Grover, Jacek Ostrowski, Lawrence G Hamann

Affiliation

¹ Bristol-Myers Squibb Research and Development, Princeton, NJ 08543-4000, USA. [email protected]

PMID: 17574413
DOI: 10.1016/j.bmcl.2007.06.007

Abstract

Replacement of the 3-oxo group of 2-chloro-4-[(7R,7aS)-7-hydroxy-1,3-dioxotetrahydro-1H-pyrrolo[1,2c]imidazol-2(3H)-yl]-3-methylbenzonitrile resulted in a sulfamide series of selective androgen receptor modulator (SARM) agonists.

MeSH terms

Androgens*
Animals
Dose-Response Relationship, Drug
Male
Molecular Structure
Muscle, Skeletal / drug effects
Muscle, Skeletal / growth & development
Prostate / drug effects
Prostate / growth & development
Protein Binding
Rats
Receptors, Androgen / metabolism
Structure-Activity Relationship
Testosterone Congeners / chemical synthesis*
Testosterone Congeners / pharmacology*
Thiadiazoles / chemical synthesis*
Thiadiazoles / pharmacology*

Substances

Androgens
Receptors, Androgen
Testosterone Congeners
Thiadiazoles