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, 21 (6), 1744-7

Design and Synthesis of Tricyclic Tetrahydroquinolines as a New Series of Nonsteroidal Selective Androgen Receptor Modulators (SARMs)

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Design and Synthesis of Tricyclic Tetrahydroquinolines as a New Series of Nonsteroidal Selective Androgen Receptor Modulators (SARMs)

Naoya Nagata et al. Bioorg Med Chem Lett.

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.

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