Synthesis and Structure-Activity Relationships of Oxamic Acid and Acetic Acid Derivatives Related to L-Thyronine

• Published in: Journal of medicinal chemistry Vol. 38; no. 4; pp. 695 - 707
• Main Authors: Yokoyama, Naokata, Walker, Gordon N, Main, Alan J, Stanton, James L, Morrissey, Michael M, Boehm, Charles, Engle, Allan, Neubert, Alan D, Wasvary, Jong M
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.02.1995; Amer Chemical Soc
• Subjects: Acetates - chemistry; Acetates - pharmacology; Acetic Acid; Animals; Biological and medical sciences; Chemistry, Medicinal; General and cellular metabolism. Vitamins; Hypolipidemic Agents - chemical synthesis; Hypolipidemic Agents - chemistry; Hypolipidemic Agents - pharmacology; Life Sciences & Biomedicine; Liver - drug effects; Liver - metabolism; Male; Medical sciences; Myocardial Contraction - drug effects; Oxamic Acid - analogs & derivatives; Oxamic Acid - chemistry; Oxamic Acid - pharmacology; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Rats; Rats, Sprague-Dawley; Receptors, Cell Surface - drug effects; Receptors, Cell Surface - metabolism; Receptors, Cytoplasmic and Nuclear - drug effects; Receptors, Cytoplasmic and Nuclear - metabolism; Science & Technology; Structure-Activity Relationship; Thyronines - chemistry; THYROID-HORMONE ANALOGS; RAT-LIVER; TRANSPORT; QUANTITATIVE STRUCTURE-ACTIVITY; THYROXINE ANALOGS; THYROMIMETIC ACTIVITIES; EXPERIMENTAL HYPOTHYROIDISM; BINDING-SITES; PLASMA-MEMBRANE; TRIIODOTHYRONINE T3; Rat; Rodentia; Oral administration; In vitro; Cholesterol; In vivo; Vertebrata; Mammalia; Structure activity relation; Animal; Phenols; Carboxamide; Dicarboxylic acid; Triiodothyronine; Fluorine Organic compounds; Chemical synthesis; Antilipemic agent

Aryloxamic acids 7 and 23, (arylamino)acetic acids 29, arylpropionic acids 33, arylthioacetic acids 37, and (aryloxy)acetic acid 41 related to L-triiodothyronine (L-T-3) were prepared and tested in vitro for binding to the rat liver nuclear L-T-3 receptor and the rat membrane L-T-3 receptor. The str...