66587-69-7

Usage

InChI:InChI=1/C8H10OS/c1-5-4-8(6(2)9)10-7(5)3/h4H,1-3H3

Upstream product

• 632-16-6 2,3-dimethylthiophene 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 7646-78-8 tin(IV) chloride 
• 5895-88-5 3-methyl-thiophene-2-carbaldehyde semicarbazone 
• 5834-16-2 3-methyl-2-thiophenecarboxaldehdye 

Downstream Products

• 399043-52-8 N-[3-(3-bromo-benzoyl)-4,5-dimethyl-thiophen-2-yl]-acetamide 
• 399043-53-9 N-[4,5-dimethyl-3-(3-methyl-benzoyl)-thiophen-2-yl]-acetamide 
• 399043-50-6 N-[3-(3-fluoro-benzoyl)-4,5-dimethyl-thiophen-2-yl]-acetamide 
• 399043-51-7 N-[3-(3-chloro-benzoyl)-4,5-dimethyl-thiophen-2-yl]-acetamide 
• 399043-19-7 (4,5-dimethyl-2-methylcarbamoyl-thiophen-3-yl)(phenyl)methanone 
• 132861-87-1 PD 81723 

Relevant academic research and scientific papers

2-amino-3-aroyl-4,5 alkylthiophenes: agonist allosteric enhancers at human A1 adenosine receptors

The present invention relates to a compound of formula (I): wherein: R3 is selected from the group consisting of 1-napthyl, 2-napthyl and cycloalkylphenyl; and R4 and R5 taken together form a ring having from 5 to 10 carbon atoms. Additionally, the invention provides a therapeutic method for preventing or treating a pathological condition or symptom in a mammal subject, such as a human, wherein increased angiogenesis is desired, comprising administering to a mammal in need of such therapy an effective amount of the aforementioned thiophene selective adenosine A1 allosteric enhancer.

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.