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  • Dicarba-closo-dodecaboranes as a pharmacophore. Retinoidal antagonists and potential agonists.

Dicarba-closo-dodecaboranes as a pharmacophore. Retinoidal antagonists and potential agonists.

Chemical & pharmaceutical bulletin (1999-04-23)
T Iijima, Y Endo, M Tsuji, E Kawachi, H Kagechika, K Shudo
ABSTRACT

Synthesis and biological evaluation of the first dicarba-closo-dodecaborane (carborane) derivatives of retinoids are described. Their retinoidal activity were examined in terms of the differentiation-inducing ability toward human promyelocytic leukemia HL-60 cells. High retinoidal activity (agonist or antagonist for retinoic acid receptor (RAR) requires a carboxylic acid moiety and an appropriate hydrophobic group located at a suitable position on the molecule. The 4-carboranyl-substituted compounds (7, 11) showed antagonistic activity but no agonistic activity even in the presence of the potent synergist HX630. On the other hand, the 3-carboranyl-substituted compounds (8, 12) showed potential agonistic activity, but no antagonistic activity. The results indicates that carboranes are applicable as the hydrophobic moiety of biologically active molecules.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
2-Ethynylanisole, 97%
Sigma-Aldrich
Ethyl 3-bromobenzoate, 98%