Synthesis of Aryl Propionamide Scaffold Containing a Pentafluorosulfanyl Moiety as SARMs

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

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Autores principales: Shao, Pingxuan, Zhou, Yan, Yang, Dehua, Wang, Ming-Wei, Lu, Wei, Jin, Jiyu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6930600/
https://www.ncbi.nlm.nih.gov/pubmed/31757115
http://dx.doi.org/10.3390/molecules24234227
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author Shao, Pingxuan
Zhou, Yan
Yang, Dehua
Wang, Ming-Wei
Lu, Wei
Jin, Jiyu
author_facet Shao, Pingxuan
Zhou, Yan
Yang, Dehua
Wang, Ming-Wei
Lu, Wei
Jin, Jiyu
author_sort Shao, Pingxuan
collection PubMed
description The pentafluorosulfane (SF(5)) group, as a more electronegative bioisostere than the trifluoromethyl (CF(3)) group, has been gaining greater attention and increasingly reported usage in medicinal chemistry. Ostarine is the selective androgen receptor modulators (SARMs) containing a CF(3) group in clinical trial III. In this study, 21 ostarine derivatives for replacing the CF(3) group with SF(5) substituents were synthesized. Some SF(5)-derivatives showed androgen receptor (AR) agonistic activities in vitro. The results pointed to the potential of using this scaffold to develop new AR agonists.
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spelling pubmed-69306002019-12-26 Synthesis of Aryl Propionamide Scaffold Containing a Pentafluorosulfanyl Moiety as SARMs Shao, Pingxuan Zhou, Yan Yang, Dehua Wang, Ming-Wei Lu, Wei Jin, Jiyu Molecules Article The pentafluorosulfane (SF(5)) group, as a more electronegative bioisostere than the trifluoromethyl (CF(3)) group, has been gaining greater attention and increasingly reported usage in medicinal chemistry. Ostarine is the selective androgen receptor modulators (SARMs) containing a CF(3) group in clinical trial III. In this study, 21 ostarine derivatives for replacing the CF(3) group with SF(5) substituents were synthesized. Some SF(5)-derivatives showed androgen receptor (AR) agonistic activities in vitro. The results pointed to the potential of using this scaffold to develop new AR agonists. MDPI 2019-11-20 /pmc/articles/PMC6930600/ /pubmed/31757115 http://dx.doi.org/10.3390/molecules24234227 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Shao, Pingxuan
Zhou, Yan
Yang, Dehua
Wang, Ming-Wei
Lu, Wei
Jin, Jiyu
Synthesis of Aryl Propionamide Scaffold Containing a Pentafluorosulfanyl Moiety as SARMs
title 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_short Synthesis of Aryl Propionamide Scaffold Containing a Pentafluorosulfanyl Moiety as SARMs
title_sort synthesis of aryl propionamide scaffold containing a pentafluorosulfanyl moiety as sarms
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6930600/
https://www.ncbi.nlm.nih.gov/pubmed/31757115
http://dx.doi.org/10.3390/molecules24234227
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