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Synthesis and preliminary investigations into novel 1,2,3-triazole-derived androgen receptor antagonists inspired by bicalutamide.

Altimari,JM, Niranjan,B, Risbridger,GP, Schweiker,SS, Lohning,AE and Henderson,LC 2014, Synthesis and preliminary investigations into novel 1,2,3-triazole-derived androgen receptor antagonists inspired by bicalutamide., Bioorganic & Medicinal Chemistry Letters, vol. 24, no. 21, pp. 4948-4953, doi: 10.1016/j.bmcl.2014.09.036.

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Title Synthesis and preliminary investigations into novel 1,2,3-triazole-derived androgen receptor antagonists inspired by bicalutamide.
Author(s) Altimari,JM
Niranjan,B
Risbridger,GP
Schweiker,SS
Lohning,AE
Henderson,LCORCID iD for Henderson,LC orcid.org/0000-0002-4244-2056
Journal name Bioorganic & Medicinal Chemistry Letters
Volume number 24
Issue number 21
Start page 4948
End page 4953
Total pages 6
Publisher Elsevier
Place of publication Doetinchem, Netherlands
Publication date 2014-11
ISSN 1464-3405
Keyword(s) Androgen receptor
Bicalutamide
Click chemistry
Molecular modeling
Prostate cancer
Triazole
Science & Technology
Life Sciences & Biomedicine
Physical Sciences
Chemistry, Medicinal
Chemistry, Organic
Pharmacology & Pharmacy
Chemistry
BIOLOGICAL EVALUATION
PROSTATE-CANCER
TERMINAL ALKYNES
DESIGN
DERIVATIVES
ACID
REPLACEMENT
METABOLISM
MODULATORS
Summary A versatile and high yielding synthesis of novel androgen receptor (AR) antagonists is presented. Using this methodology, six 1,4-substituted-1,2,3-triazole derived bicalutamide mimics were synthesised in five steps and in isolated overall yields from 41% to 85%. Evaluation of these compounds for their anti-proliferative properties against androgen dependent (LNCaP) and independent (PC-3) cells showed promising IC50 values of 34-45 μM and 29-151 μM, respectively. The data suggest that the latter compounds may be an excellent starting point for the development of prostate cancer therapeutics for both androgen dependent and independent forms of this disease. Docking of these compounds (each enantiomer) in silico into the T877A mutated androgen receptor, as possessed by LNCaP cells, was also undertaken.
Language eng
DOI 10.1016/j.bmcl.2014.09.036
Field of Research 030503 Organic Chemical Synthesis
030401 Biologically Active Molecules
Socio Economic Objective 970103 Expanding Knowledge in the Chemical Sciences
HERDC Research category C1 Refereed article in a scholarly journal
Copyright notice ©2014, Elsevier
Persistent URL http://hdl.handle.net/10536/DRO/DU:30069729

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