- Design and synthesis of iodocarborane-containing ligands with high affinity and selectivity toward ERβ
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The selectivity and the binding affinity of previously reported carborane-containing ligands 2 and 3 toward ERβ remains to be optimized. To improve their biological profiles, a series of iodinated carboranyl phenol derivatives (4–6) were designed and synthesized as prospective ERβ-selective ligands with high affinity. Several iodinated carboranyl phenols showed high relative binding affinity (RBA) values for both ERs, and especially for ERβ, due to suitable hydrophobic interactions of the iodine atoms with the hydrophobic amino acid residues of the ERβ ligand-binding domains. Among these derivatives, 9,10-diiodo-m-carborane 5f exhibited a more than 100% increase of the RBA values toward ERβ, a 14-fold increased selectivity for ERβ over ERα, and ER-agonistic activity in MCF-7 cell proliferation assays.
- Ohta, Kiminori,Ogawa, Takumi,Endo, Yasuyuki
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p. 4030 - 4033
(2017/08/22)
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- Magnesium-assisted intramolecular demethylation utilizing carborane C-H geometry
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A novel type of demethylation reaction was designed in the Pd-catalyzed coupling reaction of iodocarboranes with several Grignard reagents, CH3OPhMgBr. 3-Iodo-o-carborane 1 reacted with 2-CH3OPhMgBr to afford the corresponding phenol
- Ohta, Kiminori,Yamazaki, Hiroto,Endo, Yasuyuki
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p. 1646 - 1651
(2009/10/04)
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- Palladium-catalyzed cross-coupling reactions of arylboronic acids and 2-I-p-carborane
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p-Carborane has been arylated on the 2-B-atom in high yields, using the Suzuki-Miyaura reaction. Thus the reaction between 2-I-p-carborane and various arylboronic acids [1-naphthyl-, phenyl-, 4-MeO-C6H4-, 3-CH3CONH-C6
- Eriksson, Ludvig,Beletskaya, Irina P,Bregadze, Vladimir I,Sivaev, Igor B,Sj?berg, Stefan
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p. 267 - 272
(2007/10/03)
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