Synthesis of Aryl Propionamide Scaffold Containing a Pentafluorosulfanyl Moiety as SARMs

The pentafluorosulfane (SF<sub>5</sub>) group, as a more electronegative bioisostere than the trifluoromethyl (CF<sub>3</sub>) group, has been gaining greater attention and increasingly reported usage in medicinal chemistry. Ostarine is the selective androgen receptor modulat...

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Main Authors:	Pingxuan Shao, Yan Zhou, Dehua Yang, Ming-Wei Wang, Wei Lu, Jiyu Jin
Format:	Article
Language:	English
Published:	MDPI AG 2019-11-01
Series:	Molecules
Subjects:	pentafluorosulfanyl aryl propionamide androgen receptor agonist sarms
Online Access:	https://www.mdpi.com/1420-3049/24/23/4227

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spelling	doaj-196ced7be25e43838b308845878d1b432020-11-25T02:21:19ZengMDPI AGMolecules1420-30492019-11-012423422710.3390/molecules24234227molecules24234227Synthesis of Aryl Propionamide Scaffold Containing a Pentafluorosulfanyl Moiety as SARMsPingxuan Shao0Yan Zhou1Dehua Yang2Ming-Wei Wang3Wei Lu4Jiyu Jin5Shanghai 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, ChinaThe 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, ChinaThe 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, ChinaThe 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, ChinaShanghai 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, ChinaShanghai 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, ChinaThe pentafluorosulfane (SF<sub>5</sub>) group, as a more electronegative bioisostere than the trifluoromethyl (CF<sub>3</sub>) group, has been gaining greater attention and increasingly reported usage in medicinal chemistry. Ostarine is the selective androgen receptor modulators (SARMs) containing a CF<sub>3</sub> group in clinical trial III. In this study, 21 ostarine derivatives for replacing the CF<sub>3</sub> group with SF<sub>5</sub> substituents were synthesized. Some SF<sub>5</sub>-derivatives showed androgen receptor (AR) agonistic activities<i> </i>in vitro. The results pointed to the potential of using this scaffold to develop new AR agonists.https://www.mdpi.com/1420-3049/24/23/4227pentafluorosulfanylaryl propionamideandrogen receptoragonistsarms
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Pingxuan Shao Yan Zhou Dehua Yang Ming-Wei Wang Wei Lu Jiyu Jin
spellingShingle	Pingxuan Shao Yan Zhou Dehua Yang Ming-Wei Wang Wei Lu Jiyu Jin Synthesis of Aryl Propionamide Scaffold Containing a Pentafluorosulfanyl Moiety as SARMs Molecules pentafluorosulfanyl aryl propionamide androgen receptor agonist sarms
author_facet	Pingxuan Shao Yan Zhou Dehua Yang Ming-Wei Wang Wei Lu Jiyu Jin
author_sort	Pingxuan Shao
title	Synthesis of Aryl Propionamide Scaffold Containing a Pentafluorosulfanyl Moiety as SARMs
title_short	Synthesis of Aryl Propionamide Scaffold Containing a Pentafluorosulfanyl Moiety as SARMs
title_full	Synthesis of Aryl Propionamide Scaffold Containing a Pentafluorosulfanyl Moiety as SARMs
title_fullStr	Synthesis of Aryl Propionamide Scaffold Containing a Pentafluorosulfanyl Moiety as SARMs
title_full_unstemmed	Synthesis of Aryl Propionamide Scaffold Containing a Pentafluorosulfanyl Moiety as SARMs
title_sort	synthesis of aryl propionamide scaffold containing a pentafluorosulfanyl moiety as sarms
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2019-11-01
description	The pentafluorosulfane (SF<sub>5</sub>) group, as a more electronegative bioisostere than the trifluoromethyl (CF<sub>3</sub>) group, has been gaining greater attention and increasingly reported usage in medicinal chemistry. Ostarine is the selective androgen receptor modulators (SARMs) containing a CF<sub>3</sub> group in clinical trial III. In this study, 21 ostarine derivatives for replacing the CF<sub>3</sub> group with SF<sub>5</sub> substituents were synthesized. Some SF<sub>5</sub>-derivatives showed androgen receptor (AR) agonistic activities<i> </i>in vitro. The results pointed to the potential of using this scaffold to develop new AR agonists.
topic	pentafluorosulfanyl aryl propionamide androgen receptor agonist sarms
url	https://www.mdpi.com/1420-3049/24/23/4227
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Synthesis of Aryl Propionamide Scaffold Containing a Pentafluorosulfanyl Moiety as SARMs

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