207306-50-1

Usage

Uses

Used in Pharmaceutical Industry:
6,7-DIHYDRO-3-[(2-HYDROXYETHYL)THIO]-6,6-DIMETHYL-1-(2-THIAZOLYL)-BENZO[C]THIOPHEN-4(5H)-ONE is used as a selective GABAA α5 receptor inverse agonist for enhancing cognition. Its ability to selectively target the α5β3γ2 subunit-containing GABAA receptors makes it a promising candidate for the development of novel therapeutics aimed at improving cognitive functions.
Used in Research Applications:
In the field of scientific research, 6,7-DIHYDRO-3-[(2-HYDROXYETHYL)THIO]-6,6-DIMETHYL-1-(2-THIAZOLYL)-BENZO[C]THIOPHEN-4(5H)-ONE serves as a valuable tool for studying the role of GABAA receptors in cognitive processes and pain modulation. Its selective action on specific GABAA receptor subtypes allows researchers to gain insights into the underlying mechanisms of various neurological conditions and develop targeted treatments.
Used in Drug Development:
6,7-DIHYDRO-3-[(2-HYDROXYETHYL)THIO]-6,6-DIMETHYL-1-(2-THIAZOLYL)-BENZO[C]THIOPHEN-4(5H)-ONE holds potential for the development of new drugs targeting cognitive disorders and pain management. Its unique molecular structure and selective receptor interaction make it an attractive starting point for the design and synthesis of novel therapeutic agents.

Biological Activity

GABA A receptor inverse agonist selective for the α 5 -subtype (K i values are 1.6, 16, 20 and 20 nM for α 5, α 2, α 1 and α 3 subtypes respectively). Brain penetrant; enhances cognitive performance in rats in the delayed matching-to-place morris water maze test following i.p. administration.

Upstream product

• 207306-56-7 6,6-Dimethyl-3-methylthio-1-(thiazol-2-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one 
• 207307-82-2 6,6-dimethyl-3-methylthio-4-oxo-4,5,6,7-tetrahydro-2-benzothiophene-1-carbothioamide 
• 60-24-2 2-hydroxyethanethiol 
• 410090-78-7 6,6-dimethyl-3-methanesulphonyl-1-(thiazol-2-yl)-6,7-dihydro-2-benzothiophen-4(5H)-one 

Relevant academic research and scientific papers

6,7-Dihydro-2-benzothiophen-4(5H)-ones: A novel class of GABA-A α5 receptor inverse agonists

Nonselective inverse agonists at the benzodiazepine binding site on the GABA-A chloride ion channel enhance cognitive performance in animals but cannot be used in the treatment of cognitive disorders because of anxiogenic and convulsant side effects. We have identified a novel series of GABA-A α5 receptor ligands during our search for α5 receptor inverse agonists as potential cognition enhancers. In particular, 6,6-dimethyl-3-(2-hydroxyethyl)thio-1-(thiazol-2-yl)-6, 7-dihydro-2-benzothiophen-4(5H)-one (26) has been identified as a functionally selective GABA-A α5 inverse agonist.

Identification of a novel, selective GABAa α5 receptor inverse agonist which enhances cognition

In pursuit of a GABAA α5-subtype-selective inverse agonist to enhance cognition, a series of 6,7-dihydro-2-benzothiophen-4(5H)-ones has been identified as a novel class of GABAA receptor ligands. These thiophenes have higher binding affinity for the GABAA α5 receptor subtype compared to the GABAA α1, α2, and α3 subtypes, and several analogues exhibit high GABAA α5 receptor inverse agonism. 6,6-Dimethyl-3-(2-hydroxyethyl)thio-1-(thiazol-2-yl)-6,7-dihydro-2- benzothiophen-4(5H)-one (43) has been identified as a full inverse agonist at the GABAA α5 receptor and is functionally selective over the other major GABAA receptor subtypes. 43 readily penetrates into the CNS to give selective occupancy of GABAA α5 receptors. In addition, 43 enhances cognitive performance in rats in the delayed 'matching-to-place' Morris water maze test - a hippocampal-dependent memory task - without the convulsant or proconvulsant activity associated with nonselective, GABAA receptor inverse agonists.

Thienycyclohexanone derivatives as ligands of the GABAA α5 receptor subtype

A pharamceutical composition comprises a compound of formula (I) or a pharmaceutically acceptable salt thereof, wherein A is C1-6alkyl, C2-6alkenyl, C2-6-alkynyl, C3-6-cycloalkyl, arylC1-6alkyl, aryl, S(O)pR1.