Format

Send to

Choose Destination
Bioorg Med Chem Lett. 2011 Mar 15;21(6):1744-7. doi: 10.1016/j.bmcl.2011.01.073. Epub 2011 Feb 2.

Design and synthesis of tricyclic tetrahydroquinolines as a new series of nonsteroidal selective androgen receptor modulators (SARMs).

Author information

1
Central Research Laboratories, Kaken Pharmaceutical Co., Ltd, Yamashina, Kyoto, Japan. nagata_naoya@kaken.co.jp

Abstract

Some tricyclic tetrahydroquinolines (THQs) were found to have the potential of a new series of nonsteroidal selective androgen receptor modulators (SARMs). Compound 5b was first designed and synthesized under our hypothesis based on a four-point pharmacophoric requirement of the 3-carbonyl, 18-methyl, 17-hydroxyl, and 13-quaternary carbon groups of dihydrotestosterone (DHT). It was revealed that this compound exhibits not only a strong androgen receptor (AR) agonistic activity (EC(50)=9.2 nM) but also the highest selectivity in binding affinity to AR among the steroid hormone receptors. Furthermore, this compound showed a weak virilizing effect with retention of the desired anabolic effect as compared with DHT in vivo.

PMID:
21349712
DOI:
10.1016/j.bmcl.2011.01.073
[Indexed for MEDLINE]

Supplemental Content

Full text links

Icon for Elsevier Science
Loading ...
Support Center