Design and synthesis of carborane-containing androgen receptor (AR) antagonist bearing a pyridine ring

Bioorganic & Medicinal Chemistry
Kiminori OhtaYasuyuki Endo

Abstract

We previously developed carborane-containing potent AR antagonists, BA321 and BA341, on the basis of our hypothesis that the carborane cage would be an excellent hydrophobic pharmacophore in place of steroidal C and D rings. As an extension of that work, we designed and synthesized carborane-containing AR antagonist candidates with a pyridine ring. Compound 6b, which has a pyridine ring directly bound to the p-carborane cage at the 3-position, exhibited potent AR-antagonistic activity in transcriptional activation assay using NIH3T3 cells transfected with a hAR-expression plasmid. In addition, it showed more potent antiandrogenic activity than that of the well-known antiandrogen flutamide and comparable activity to that of (R)-bicalutamide in SC-3 cell proliferation assay.

References

Jun 1, 1975·Journal of Steroid Biochemistry·R O Neri, E A Peets

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Citations

Jul 26, 2011·Chemical Reviews·Matthias Scholz, Evamarie Hey-Hawkins
Jul 3, 2016·European Journal of Medicinal Chemistry·Asako KaiseYasuyuki Endo
Mar 3, 2009·Chemical & Pharmaceutical Bulletin·Kiminori OhtaYasuyuki Endo
Aug 8, 2020·International Journal of Molecular Sciences·Hitomi KogaAya Tanatani

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