59108-43-9

Usage

Uses

Used in Pharmaceutical Industry:
8-BROMO-2-(TRIFLUOROMETHYL)QUINOLIN-4-OL is used as a pharmaceutical compound for its potential biological activities. As a quinoline derivative, it has been studied for its antimicrobial, anticancer, and anti-inflammatory properties, making it a promising candidate for the development of new drugs.
Used in Organic Synthesis:
8-BROMO-2-(TRIFLUOROMETHYL)QUINOLIN-4-OL is used as a building block in the synthesis of other organic compounds. Its unique structure, with the bromine and trifluoromethyl groups, may provide new pathways for the creation of novel molecules with specific properties.
Used in Medicinal Chemistry Research and Development:
Due to its distinctive chemical structure, 8-BROMO-2-(TRIFLUOROMETHYL)QUINOLIN-4-OL is used as a subject of research and development in the field of medicinal chemistry. Further studies may reveal additional applications and enhance understanding of its potential therapeutic effects.

InChI:InChI=1/C10H5BrF3NO/c11-6-3-1-2-5-7(16)4-8(10(12,13)14)15-9(5)6/h1-4H,(H,15,16)

Upstream product

• 372-31-6 ethyl 4,4,4-trifluoroacetoacetate 
• 615-36-1 2-bromoaniline 

Downstream Products

• 587885-93-6 4,8-dibromo-2-(trifluoromethyl)quinoline 

Relevant academic research and scientific papers

QUINOLINE DERIVATIVES AS SMO INHIBITORS

Disclosed are quinoline derivatives as hedgehog pathway inhibitors, especially as SMO inhibitors. Compounds of the present invention can be used in treating diseases relating to hedgehog pathway including cancer.

The synthesis and biological evaluation of quinolyl-piperazinyl piperidines as potent serotonin 5-HT1A antagonists

As part of an effort to identify 5-HT1A antagonists that did not possess typical arylalkylamine or keto/amido-alkyl aryl piperazine scaffolds, prototype compound 10a was identified from earlier work in a combined 5-HT 1A antagonist/SSRI program. This quinolyl-piperazinyl piperidine analogue displayed potent, selective 5-HT1A antagonism but suffered from poor oxidative metabolic stability, resulting in low exposure following oral administration. SAR studies, driven primarily by in vitro liver microsomal stability assessment, identified compound 10b, which displayed improved oral bioavailability and lower intrinsic clearance. Further changes to the scaffold (e.g., 10r) resulted in a loss in potency. Compound 10b displayed cognitive enhancing effects in a number of animal models of learning and memory, enhanced the antidepressant-like effects of the SSRI fluoxetine, and reversed the sexual dysfunction induced by chronic fluoxetine treatment.

Selective and efficient structural elaboration of 2-(trifluoromethyl)quinolinones

The acid-catalyzed cyclization-condensation between anilines and ethyl 4,4,4-trifluoroacetoacetate affords 1,4-dihydro-2-trifluoromethyl-4H-4-quinolinones (1), which can easily be converted into 4-bromo-2-(trifluoromethyl)quinolines. These undergo halogen/metal exchange, generating 2-trifluoromethyl-4-quinolyllithiums, when treated with butyllithium, and hydrogen/metal exchange, generating 4-bromo-2-trifluoromethyl-3-quinolyllithiums, when treated with lithium diisopropylamide. Trapping of the latter intermediates provides 3-functionalized products that may be further elaborated by electrophilic substitution of the bromine atom. A few unexpected findings resulted from these investigations, the most noteworthy being an unprecedented buttressing effect and a counterintuitive halogen reactivity. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).