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Synthesis and Biological Evaluation of Novel M-Carborane-Containing Estrogen Receptor Partial Agonists as SERM Candidates

Synthesis and Biological Evaluation of Novel M-Carborane-Containing Estrogen Receptor Partial Agonists as SERM Candidates

Kiminori Ohta, Takumi Ogawa, Asako Kaise, Yasuyuki Endo

Bioorg Med Chem Lett. 2015 Aug 15;25(16):3213-6.

PMID: 26077489

Abstract:

We designed and synthesized novel m-carborane-containing selective estrogen receptor modulator (SERM) candidates using previously reported m-carborane-containing ER partial agonist 1 as the lead compound. Biological activities were evaluated by means of ERα competitive binding assay and MCF-7 cell proliferation assay. Re-positioning the N,N-dimethylaminoethyloxy group at the para position of 1 to the meta position enhanced the ERα-binding affinity, and 4c showed the highest relative binding affinity (RBA: 83 vs 17β-estradiol = 100) among the tested compounds. Compound 4b showed the most potent ER-agonist activity (EC50: 1.4 nM) and the lowest maximal efficacy (Emax: 50%) in MCF-7 cell proliferation assay. Inhibition of 0.1 nM 17β-estradiol-induced MCF-7 cell proliferation by 4b (IC50: 0.4 μM) was at least 10 times more potent than that of the lead compound 1.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP16986246	m-Carborane		16986-24-6	Price

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