538326-91-9

Upstream product

• 451-40-1 phenyl benzyl ketone 
• 71-43-2 benzene 
• 103-80-0 phenylacetyl chloride 
• 14442-50-3 2-cyano-3,4-diphenyl-crotonic acid ethyl ester 
• 4815-43-4 2-amino-4,5-diphenyl-thiophene-3-carboxylic acid ethyl ester 
• 407-25-0 trifluoroacetic anhydride 

Downstream Products

• 538326-96-4 N-[3-(biphenyl-4-carbonyl)-4,5-diphenylthiophen-2-yl]-2,2,2-trifluoroacetamide 
• 538326-97-5 N-[3-(naphthalene-2-carbonyl)-4,5-diphenylthiophen-2-yl]-2,2,2-trifluoroacetamide 
• 538326-95-3 N-[3-(4-chlorobenzoyl)-4,5-diphenylthiophen-2-yl]-2,2,2-trifluoroacetamide 
• 538326-94-2 N-[3-(3-chlorobenzoyl)-4,5-diphenylthiophen-2-yl]-2,2,2-trifluoroacetamide 

Relevant academic research and scientific papers

2-Amino-3-benzoylthiophene allosteric enhancers of A1, adenosine agonist binding: New 3, 4-, and 5-modifications

2-Amino-3-aroylthiophenes are agonist allosteric enhancers (AE) at the A1, adenosine receptor (A1AR). Here we report the syntheses of three kinds of novel 2-aminothiophenes and assays of their AE activity at the human A1AR (hA1AR), namely, (1) 2-amino-4,5-diphenylthiophene-3-carboxylates, 3a-h, (2) 2-amino-3-benzoyl-4,5-diphenylthiophenes, 7a-p, and (3) 2-amino-5-bromo-3-benzoyl-4-phenylthiophenes, 10a-h. An in vitro assay employing the A1AR agonist [125I]ABA and membranes from CHO-K1 cells stably expressing the hA1AR measured an index of AE activity, the ability of a candidate AE to stabilize the agonist-A1AR-G protein ternary complex, scored as the percentage of ternary complex remaining after 10 min of dissociation initiated by CPX and GTPγS. The AE activity score of 2-amino-4,5-dimethyl-3-(3-trifluoromethylbenzoyl)thiophene (PD 81,723), which was 19%, served as a standard for comparison. Two 3-carboxythiophene 3-trifluoromethylbenzyl esters, 3d (49%) and 3f (63%), had substantial AE activity. The 3-(1-naphthoyl) substituent of 7e (52%) also supported AE activity. Compounds in series 3 tended to be more potent, 10a and 10c having scores of 91 and 80%, respectively. The activity of 2-amino-5-bromo-3-ethoxycarbonyl-4-(3-nitrophenyl)thiophene, 10h (26%), is an exception to the rule that a 3-ethoxycarbonyl substituent cannot support AE activity.