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Design and Synthesis of Boron Containing Potential pan-RAR Inverse Agonists

Design and Synthesis of Boron Containing Potential pan-RAR Inverse Agonists

Bhaskar C Das, Xiang-Ying Tang, Todd Evans

Tetrahedron Lett. 2012 Mar 14;53(11):1316-1318.

PMID: 23180890

Abstract:

We designed and successfully synthesized the compounds 5 and 8 as potential pan-RAR (retinoic acid receptor) agonists. These two compounds were designed based on an existing pan-RAR agonist (BMS493). We synthesized compound 5, in which the carboxylic acid group in BMS 493 was replaced by boronic ester; and compound 8, in which the double bond of BMS 493 was changed to an oxadiazole (as bioisosteres of double bond) ring. The two target molecules 5 and 8 were synthesized from the commercially available 7-bromo-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-one 1. Compound 1 was derivatized to intermediate 5,5-dimethyl-8-(phenylethynyl)-5,6-dihydronaphthalene-2 carbaldehyde 4 by using alkylation, dehydration, and metal exchange reactions. The intermediate 4 was further converted to 5 by using a Wittig reaction and to 8 by amide coupling and dehydration to give overall 18% and 33% yields, respectively, after 8 steps in each case.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP215030903	BMS 493		215030-90-3	Price

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