Synthesis of androgen receptor antagonists containing a pentafluorosulfanyl (SF                         5                         ) moiety

Jiyu Jin; Yan Zhou; Dehua Yang; Qiumeng Zhang; Ming Wei Wang; Wei Lu

doi:10.1002/ardp.201800175

Synthesis of androgen receptor antagonists containing a pentafluorosulfanyl (SF ₅ ) moiety

Jiyu Jin
, Yan Zhou
, Dehua Yang
, Qiumeng Zhang
, Ming Wei Wang^*
, Wei Lu

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University
CAS - Shanghai Institute of Materia Medica

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

8 Scopus citations

Abstract

A novel scaffold of pentafluorosulfanyl (SF ₅ )-containing enzalutamide analogues was discovered for potent androgen receptor (AR) antagonists through rational drug design. Several compounds showed good biological profiles in AR binding. Of the derivatives studied, compound 8a had potent AR antagonist activity (IC ₅₀ = 7.1 ± 1.0 µM) and high efficacy (104.5 ± 12.8%). It exhibited an inhibitory effect comparable to that of enzalutamide (inhibition = 66.0 and 77.9%, respectively) in a prostate cancer cell line. The results point to the potential of using this scaffold to develop new AR antagonists.

Original language	English
Article number	1800175
Journal	Archiv der Pharmazie
Volume	351
Issue number	11
DOIs	https://doi.org/10.1002/ardp.201800175
State	Published - Nov 2018

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

androgen receptor
antagonist
enzalutamide
pentafluorosulfanyl

Access to Document

10.1002/ardp.201800175

Cite this

@article{2019abc1762b450f842ff75a53623cef,

title = " Synthesis of androgen receptor antagonists containing a pentafluorosulfanyl (SF 5 ) moiety ",

abstract = " A novel scaffold of pentafluorosulfanyl (SF 5 )-containing enzalutamide analogues was discovered for potent androgen receptor (AR) antagonists through rational drug design. Several compounds showed good biological profiles in AR binding. Of the derivatives studied, compound 8a had potent AR antagonist activity (IC 50 = 7.1 ± 1.0 µM) and high efficacy (104.5 ± 12.8\%). It exhibited an inhibitory effect comparable to that of enzalutamide (inhibition = 66.0 and 77.9\%, respectively) in a prostate cancer cell line. The results point to the potential of using this scaffold to develop new AR antagonists.",

keywords = "androgen receptor, antagonist, enzalutamide, pentafluorosulfanyl",

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

note = "Publisher Copyright: {\textcopyright} 2018 Deutsche Pharmazeutische Gesellschaft",

year = "2018",

month = nov,

doi = "10.1002/ardp.201800175",

language = "英语",

volume = "351",

journal = "Archiv der Pharmazie",

issn = "0365-6233",

publisher = "Wiley-VCH Verlag",

number = "11",

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TY - JOUR

T1 - Synthesis of androgen receptor antagonists containing a pentafluorosulfanyl (SF 5 ) moiety

AU - Jin, Jiyu

AU - Zhou, Yan

AU - Yang, Dehua

AU - Zhang, Qiumeng

AU - Wang, Ming Wei

AU - Lu, Wei

PY - 2018/11

Y1 - 2018/11

N2 - A novel scaffold of pentafluorosulfanyl (SF 5 )-containing enzalutamide analogues was discovered for potent androgen receptor (AR) antagonists through rational drug design. Several compounds showed good biological profiles in AR binding. Of the derivatives studied, compound 8a had potent AR antagonist activity (IC 50 = 7.1 ± 1.0 µM) and high efficacy (104.5 ± 12.8%). It exhibited an inhibitory effect comparable to that of enzalutamide (inhibition = 66.0 and 77.9%, respectively) in a prostate cancer cell line. The results point to the potential of using this scaffold to develop new AR antagonists.

AB - A novel scaffold of pentafluorosulfanyl (SF 5 )-containing enzalutamide analogues was discovered for potent androgen receptor (AR) antagonists through rational drug design. Several compounds showed good biological profiles in AR binding. Of the derivatives studied, compound 8a had potent AR antagonist activity (IC 50 = 7.1 ± 1.0 µM) and high efficacy (104.5 ± 12.8%). It exhibited an inhibitory effect comparable to that of enzalutamide (inhibition = 66.0 and 77.9%, respectively) in a prostate cancer cell line. The results point to the potential of using this scaffold to develop new AR antagonists.

KW - androgen receptor

KW - antagonist

KW - enzalutamide

KW - pentafluorosulfanyl

UR - https://www.scopus.com/pages/publications/85054920392

U2 - 10.1002/ardp.201800175

DO - 10.1002/ardp.201800175

M3 - 文章

C2 - 30318752

AN - SCOPUS:85054920392

SN - 0365-6233

VL - 351

JO - Archiv der Pharmazie

JF - Archiv der Pharmazie

IS - 11

M1 - 1800175

ER -