Synthesis of Aryl Propionamide Scaffold Containing a Pentafluorosulfanyl Moiety as SARMs

Pingxuan Shao; Yan Zhou; Dehua Yang; Ming-Wei Wang; Wei Lu; Jiyu Jin

doi:10.3390/molecules24234227

Synthesis of Aryl Propionamide Scaffold Containing a Pentafluorosulfanyl Moiety as SARMs

Molecules. 2019 Nov 20;24(23):4227. doi: 10.3390/molecules24234227.

Authors

Pingxuan Shao¹, Yan Zhou², Dehua Yang², Ming-Wei Wang², Wei Lu¹, Jiyu Jin¹

Affiliations

¹ Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, China.
² The National Center for Drug Screening and the CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences (CAS), 189 Guo Shou Jing Road, Shanghai, China.

Abstract

The pentafluorosulfane (SF₅) group, as a more electronegative bioisostere than the trifluoromethyl (CF₃) group, has been gaining greater attention and increasingly reported usage in medicinal chemistry. Ostarine is the selective androgen receptor modulators (SARMs) containing a CF₃ group in clinical trial III. In this study, 21 ostarine derivatives for replacing the CF₃ group with SF₅ substituents were synthesized. Some SF₅-derivatives showed androgen receptor (AR) agonistic activities in vitro. The results pointed to the potential of using this scaffold to develop new AR agonists.

Keywords: SARMs; agonist; androgen receptor; aryl propionamide; pentafluorosulfanyl.

MeSH terms

Amides* / chemistry
Amides* / pharmacology
Androgens* / chemical synthesis
Androgens* / chemistry
Androgens* / pharmacology
Anilides* / chemistry
Anilides* / pharmacology
Animals
Cell Line
Mice
Receptors, Androgen / metabolism*

Substances

Amides
Androgens
Anilides
Receptors, Androgen
ostarine
propionamide

Abstract

MeSH terms

Substances

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