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Research article2007Peer reviewed

Thyroid receptor ligands. Part 8: Thyromimetics derived from N-acylated-alpha-amino acid derivatives displaying modulated pharmacological selectivity compared with KB-141

Garg, Neeraj; Li, Yi-Lin; Collazo, Ana Maria Garcia; Litten, Chris; Ryono, Denis E.; Zhang, Minsheng; Caringal, Yolanda; Brigance, Robert P.; Meng, Wei; Washburn, William N.; Agback, Peter; Mellstrom, Karin; Rehnmark, Stefan; Rahimi-Ghadim, Mahmoud; Norin, Thomas; Grynfarb, Marlena; Sandberg, Johnny; Grover, Gary; Malm, Johan

Abstract

Based on the scaffold of the pharmacologically selective thyromimetic 2b, structurally a close analog to KB-141 (2a), a number of novel N-acylated-alpha-amino acid derivatives were synthesized and tested in a TR radioligand binding assay as well as in a reporter cell assay. On the basis of TR beta(1)-isoform selectivity and affinity, as well as affinity to the reporter cell assay, 3d was selected for further studies in the cholesterol-fed rat model. In this model 3d revealed an improved therapeutic window between cholesterol and TSH lowering but decreased margins versus tachycardia compared with 2a. (c) 2007 Elsevier Ltd. All rights reserved.

Keywords

KB-141; thyromimetic; alpha-amino acid; binding assay; TR beta-selective; cholesterol-fed rat model; cholesterol; thyroid stimulating hormone; tachycardia

Published in

Bioorganic and Medicinal Chemistry Letters
2007, Volume: 17, number: 15, pages: 4131-4134 Publisher: PERGAMON-ELSEVIER SCIENCE LTD

    UKÄ Subject classification

    Organic Chemistry

    Publication identifier

    DOI: https://doi.org/10.1016/j.bmcl.2007.05.049

    Permanent link to this page (URI)

    https://res.slu.se/id/publ/83873