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3H-Imidazo[4,5-b]pyridine-6-carboxylic Acid Derivatives as Rexinoids With Reduced Teratogenicity

3H-Imidazo[4,5-b]pyridine-6-carboxylic Acid Derivatives as Rexinoids With Reduced Teratogenicity

Yuta Takamura, Manami Takahashi, Midori Nishii, Osamu Shibahara, Masaki Watanabe, Michiko Fujihara, Hiroki Kakuta

Bioorg Med Chem Lett. 2019 Aug 1;29(15):1891-1894.

PMID: 31160175

Abstract:

Several retinoid X receptor (RXR) ligands (rexinoids), such as bexarotene (1), exhibit teratogenicity, which is a serious impediment to their clinical application. We considered that rexinoids with a lower level of maximal RXR transcription activation (i.e., partial agonists) and lower lipid solubility might show weaker adverse side effects. Based on this idea, we modified our previously reported pentamethyltetralin-type RXR partial agonists 5 and 6 to reduce their lipophilicity. Here, we report a new RXR partial agonist, 3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine-6-carboxylic acid (8, CATF-PMN), which showed greatly reduced teratogenicity in zebrafish embryos.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
LS7931260	Imidazo[1,2-a]pyridine-6-boronic acid			Price

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