261913-76-2Relevant articles and documents
Synthesis and human β-adrenoceptor activity of 1-(3,5-diiodo-4- methoxybenzyl)-1,2,3,4-tetrahydroisoquinolin-6-ol derivatives in vitro
He, Yali,Nikulin, Victor I.,Vansal, Sandeep S.,Feller, Dennis R.,Miller, Duane D.
, p. 591 - 598 (2007/10/03)
Trimetoquinol (1, TMQ) is a potent nonselective β-adrenergic receptor (AR) agonist and a thromboxane A2/prostaglandin endoperoxide (TP) receptor antagonist, while 3',5'-diiodo-TMQ (2) exhibits β3-AR selectivity. In search of selective β3-AR agonists as potential drugs for the treatment of human obesity and type II diabetes mellitus, a series of 1-(3,5-diiodo-4- methoxybenzyl)-1,2,3,4-tetrahydroisoquinolin-6-ols has been prepared and evaluated for their biological activities at human β1-, β2-, and β3-ARs expressed in Chinese hamster ovary (CHO) cells. The compounds have been synthesized by the Bischler-Napieralski cyclization of corresponding amides followed by NaBH4 reduction, and the halogens in the aromatic ring A were introduced by direct halogenation of protected compound 11. Whereas halogen substitution in ring A reduced either potency or intrinsic activity on β3- AR, the non-halogen-substituted compounds 8 and 10 were potent, selective, nearly full agonists for β3-AR.
