132861-87-1

Usage

Uses

Used in Pharmaceutical Industry:
(2-AMINO-4,5-DIMETHYL-3-THIENYL)-[3-(TRIFLUOROMETHYL)PHENYL]METHANONE is used as an allosteric potentiator for enhancing the functional effects of adenosine and adenosine analogs. This application is particularly relevant in the development of new therapeutic strategies for various medical conditions, as adenosine plays a crucial role in regulating cellular processes and signaling pathways.
Used in Chemical Research:
Due to its unique molecular structure, (2-AMINO-4,5-DIMETHYL-3-THIENYL)-[3-(TRIFLUOROMETHYL)PHENYL]METHANONE may also be used as a starting material or intermediate in the synthesis of other complex organic compounds. Its potential applications in chemical research could include the development of new drugs, materials, or catalysts.

Biological Activity

Allosteric potentiator at the adenosine A 1 receptor; acts via agonist-dependent and -independent mechanisms. Enhances agonist affinity for, and increased t 1/2 of dissociation from, the receptor. Also inhibits basal and forskolin-stimulated adenylyl cyclase (AC) activity in A 1 receptors expressed in CHO cells, possibly via direct potentiation of constitutive receptor activity or by direct inhibition of AC. Active in vivo .

InChI:InChI=1/C14H12F3NOS/c1-7-8(2)20-13(18)11(7)12(19)9-4-3-5-10(6-9)14(15,16)17/h3-6H,18H2,1-2H3

Upstream product

• 5834-16-2 3-methyl-2-thiophenecarboxaldehdye 
• 66587-69-7 (4,5-dimethyl-2-thienyl)(methyl)methanone 
• 1190954-51-8 C₁₄H₁₂F₃NO 
• 27328-86-5 3-trifluoromethylbenzoylacetonitrile 
• 78-93-3 butanone 
• 515860-74-9 1-(4,5-dimethyl-2-thiophen-2-yl)-ethanone oxime 
• 51948-20-0 N-(4,5-dimethyl-thiophen-2-yl)acetamide 
• 2251-65-2 3-(Trifluoromethyl)benzoyl chloride 
• 632-16-6 2,3-dimethylthiophene 

Relevant academic research and scientific papers

Reaction pathways to 2-aminothiophenes and thiophene-3-carbonitriles

Over the past two decades 2-amino-3-benzoylthiophenes have been found to act as allosteric enhancers of the adenosine A1 receptor (A 1AR). As such, compounds of this type have potential applications in the therapy of a variety of dis

2-Amino-3-aroyl-4,5-alkylthiophenes: Agonist allosteric enhancers at human a1 adenosine receptors

2-Amino-3-benzoylthiophenes are allosteric enhancers (AE) of agonist activity at the A1 adenosine receptor. The present report describes syntheses and assays of the AE activity at the human A1AR (hA1AR) of a panel of compounds consisting of nine 2-amino-3-aroylthiophenes (3a-i), eight 2-amino-3-benzoyl-4,5-dimethylthiophenes (12a-h), three 3-aroyl-2-carboxy-4,5-dimethylthiophenes (15a-c), 10 2-amino-3-benzoyl-5,6-dihydro-4H-cyclopenta[b]thiophenes (17a-j), 14 2-amino-3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophenes (18a-n), and 15 2-amino-3-benzoyl-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophenes (19a-o). An in vitro assay employing the A1AR agonist [125I]ABA and membranes from CHO-K1 cells stably expressing the hA1AR measured, as an index of AE activity, the ability of a candidate AE to stabilize the agonist-A1AR-G protein ternary complex. Compounds 3a-i had little or no AE activity, and compounds 12a-h had only modest activity, evidence that AE activity depended absolutely on the presence of at least a methyl group at C-4 and C-5. Compounds 17a-c lacked AE activity, suggesting the 2-amino group is essential. Polymethylene bridges linked thiophene C-4 and C-5 of compounds 17a-j, 18a-n, and 19a-o. AE activity increased with the size of the -(CH2)n- bridge, n = 3 1AR contains an allosteric binding site able to accommodate 3-aroyl substituents that are bulky and/or hydrophobic but not necessarily planar. A second region in the allosteric binding site interacts constructively with alkyl substituents at thiophene C-4 and/or C-5.

THIOPHENES USEFUL FOR MODULATING THE ADENOSINE RECEPTOR

The present invention relates to compounds of formulas (IA), (IB), and (IC): STR1 the preparation thereof, pharmaceutical formulations thereof, and their use in medicine as allosteric adenosine receptor modulators for uses including protection against hypoxia and ischemia induced injury and treatment of adenosine-sensitive cardiac arrhythmias.