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

Pingxuan Shao
, Yan Zhou
, Dehua Yang
, Ming Wei Wang^*
, Wei Lu
, Jiyu Jin

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

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.

Original language	English
Article number	4227
Journal	Molecules
Volume	24
Issue number	23
DOIs	https://doi.org/10.3390/molecules24234227
State	Published - 20 Nov 2019

Keywords

Agonist
Androgen receptor
Aryl propionamide
Pentafluorosulfanyl
SARMs

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10.3390/molecules24234227

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@article{7e26f5a00d3f4f36ae22cd998ab5c809,

title = "Synthesis of aryl propionamide scaffold containing a pentafluorosulfanyl moiety as SARMs",

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 = "Agonist, Androgen receptor, Aryl propionamide, Pentafluorosulfanyl, SARMs",

author = "Pingxuan Shao and Yan Zhou and Dehua Yang and Wang, \{Ming Wei\} and Wei Lu and Jiyu Jin",

note = "Publisher Copyright: {\textcopyright} 2019 by the authors.",

year = "2019",

month = nov,

day = "20",

doi = "10.3390/molecules24234227",

language = "英语",

volume = "24",

journal = "Molecules",

issn = "1420-3049",

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number = "23",

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TY - JOUR

T1 - Synthesis of aryl propionamide scaffold containing a pentafluorosulfanyl moiety as SARMs

AU - Shao, Pingxuan

AU - Zhou, Yan

AU - Yang, Dehua

AU - Wang, Ming Wei

AU - Lu, Wei

AU - Jin, Jiyu

PY - 2019/11/20

Y1 - 2019/11/20

N2 - 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.

AB - 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.

KW - Agonist

KW - Androgen receptor

KW - Aryl propionamide

KW - Pentafluorosulfanyl

KW - SARMs

UR - https://www.scopus.com/pages/publications/85075423277

U2 - 10.3390/molecules24234227

DO - 10.3390/molecules24234227

M3 - 文章

C2 - 31757115

AN - SCOPUS:85075423277

SN - 1420-3049

VL - 24

JO - Molecules

JF - Molecules

IS - 23

M1 - 4227

ER -

Synthesis of aryl propionamide scaffold containing a pentafluorosulfanyl moiety as SARMs

Abstract

Keywords

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