175202-29-6

Usage

Uses

Used in Medicinal Chemistry:
2-[1-METHYL-3-(TRIFLUOROMETHYL)PYRAZOL-5-YL]-THIOPHENE-5-CARBOXYLIC ACID is used as a building block for the development of new pharmaceuticals, leveraging its unique properties to improve the efficacy and selectivity of drug candidates.
Used in Drug Synthesis:
In the pharmaceutical industry, 2-[1-METHYL-3-(TRIFLUOROMETHYL)PYRAZOL-5-YL]-THIOPHENE-5-CARBOXYLIC ACID serves as an intermediate in the synthesis of various organic molecules, potentially leading to the creation of novel drugs with enhanced therapeutic profiles.
Further research and investigations are necessary to explore the full potential of 2-[1-METHYL-3-(TRIFLUOROMETHYL)PYRAZOL-5-YL]-THIOPHENE-5-CARBOXYLIC ACID in different applications, including but not limited to medicinal chemistry and drug development.

InChI:InChI=1/C10H7F3N2O2S/c1-15-5(4-8(14-15)10(11,12)13)6-2-3-7(18-6)9(16)17/h2-4H,1H3,(H,16,17)

Upstream product

• 679396-71-5 ethyl 5-(4,4,4-trifluoro-3-oxobutanoyl)thiophene-2-carboxylate 
• 33148-82-2 5-acetyl-thiophene-2-carboxylic acid ethyl ester 
• 326-91-0 1,1,1-trifluoro-4-(2-thienyl)butane-2,4-dione 
• 88-15-3 2-Acetylthiophene 
• 683274-56-8 1-methyl-5-(2-thienyl)-3-trifluoromethyl-1H-pyrazole 
• 223500-08-1 ethyl 5-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)thiophene-2-carboxylate 

Downstream Products

• 900865-51-2 5-(2-methyl-5-trifluoromethyl-2H-pyrazol-3-yl)-thiophene-2-carboxylic acid (4-nitro-phenyl)-amide 

Relevant academic research and scientific papers

Identification of 5-(1-Methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)thiophene-2-Carboxamides as Novel and Selective Monoamine Oxidase B Inhibitors Used to Improve Memory and Cognition

Initial work in Drosophila and mice demonstrated that the transcription factor cyclic adenosine monophosphate (cAMP) response element binding protein (CREB) is a master control gene for memory formation. The relationship between CREB and memory has also been found to be true in other species, including aplysia and rats. It is thus well-established that CREB activation plays a central role in memory enhancement and that CREB is activated during memory formation. On the basis of these findings, a phenotypic high-throughput screening campaign utilizing a CRE-luciferase (CRE-Luci) SK-N-MC cell line was performed to identify compounds that enhance transcriptional activation of the CRE promoter with a suboptimal dose of forskolin. A number of small-molecule hits of unknown mechanisms of action were identified in the screening campaign, including HT-0411. Follow-up studies suggested that the CREB activation by HT-0411 is attributed to its specific and selective inhibition of monoamine oxidase B (MAO-B). Further, HT-0411 was shown to improve 24 h memory in rodents in a contextual fear conditioning model. This report describes the lead optimization of a series of 5-(1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl) thiophene-2-carboxamides that were identified as novel, potent, and selective inhibitors of MAO-B. Extensive SAR studies and in vivo behavioral evaluations of this and other related analogue series identified a number of potential clinical development candidates; ultimately, compound 8f was identified as a candidate molecule with high selectivity toward MAO-B (29-56 nM) over MAO-A (19% inhibition at a screening concentration of 50 μM), an excellent profile against a panel of other enzymes and receptors, good pharmacokinetic properties in rodents and dogs, and efficacy in multiple rodent memory models.

Novel potent and selective calcium-release-activated calcium (CRAC) channel inhibitors. Part 1: Synthesis and inhibitory activity of 5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)-2-thiophenecarboxamides

We synthesized and evaluated a series of 5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)-2-thiophenecarboxamides to identify potent inhibitors of calcium-release-activated calcium (CRAC) channels with greater selectivity than voltage-operated calcium (VOC) channels. These efforts resulted in identification of compounds 22 and 24. The former exhibits highly potent and selective CRAC channel inhibitory activity, and the latter inhibited phytohemagglutinin-induced interleukin-2 production by Jurkat T lymphocytes and concanavalin A-induced hepatitis in mice.