21168-42-3

Usage

Uses

Used in Pharmaceutical Industry:
4-CHLORO-7-TRIFLUOROMETHYLQUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER is used as a key building block for the synthesis of various pharmaceutical products, particularly for the development of new drugs. It plays a crucial role in the creation of medications aimed at treating bacterial and viral infections, offering a valuable contribution to the advancement of medical treatments.
Used in Agrochemical Industry:
In the field of agrochemicals, 4-CHLORO-7-TRIFLUOROMETHYLQUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER is utilized as a key intermediate in the production of crop protection products. Its application in this industry is essential for developing effective solutions to protect crops from pests and diseases, thereby ensuring agricultural productivity and food security.
The specific uses and properties of 4-CHLORO-7-TRIFLUOROMETHYLQUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER may vary depending on the intended application and industry, highlighting its versatility and importance in both pharmaceutical and agrochemical sectors.

InChI:InChI=1/C13H9ClF3NO2/c1-2-20-12(19)9-6-18-10-5-7(13(15,16)17)3-4-8(10)11(9)14/h3-6H,2H2,1H3

Upstream product

• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 98-16-8 3-trifluoromethylaniline 
• 391-02-6 ethyl 4-oxo-7-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylate 
• 370-35-4 diethyl 2-({[3-(trifluoromethyl)phenyl]amino}methylidene)propanedioate 
• 391-02-6 4-hydroxy-7-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester 

Downstream Products

• 206257-96-7 4-[Benzyl-(4-methoxy-benzenesulfonyl)-amino]-7-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester 
• 127446-96-2 SR 26241 
• 944770-58-5 4-morpholin-1-yl-7-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester 
• 1373767-14-6 ethyl 2-(3-chlorophenyl)-4-oxo-7-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylate 
• 1373767-13-5 ethyl 4-oxo-2-(3-(trifluoromethoxy)phenyl)-7-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylate 
• 1373767-12-4 ethyl 2-(3-methoxyphenyl)-4-oxo-7-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylate 

Relevant academic research and scientific papers

Defined concatenated α6α1β3γ2 GABAA receptor constructs reveal dual action of pyrazoloquinolinone allosteric modulators

Pyrazoloquinolinones (PQs) have been extensively studied as modulators of GABAA receptors with different subunit composition, exerting modulatory effects by binding at α+/β- interfaces of GABAA receptors. PQs with a substituent in position R7 have been reported to preferentially modulate α6- subunit containing GABAA receptors which are mostly expressed in the cerebellum but were also found in the olfactory bulb, in the cochlear nucleus, in the hippocampus and in the trigeminal sensory pathway. They are considered potentially interesting in the context of sensori-motor gating deficits, depressive-like behavior, migraine and orofacial pain. Here we explored the option to modify the lead ligands’ R7 position. In the compound series we observed two different patterns of allosteric modulation in recombinantly expressed α6β3γ2 receptors, namely monophasic and biphasic positive modulation. In the latter case the additional phase occurred in the nanomolar range, while all compounds displayed robust modulation in the micromolar range. Nanomolar, near silent binding has been reported to occur at benzodiazepine binding sites, but was not investigated at the diazepam insensitive α6+/γ2- interface. To clarify the mechanism underlying the biphasic effect we tested one of the compounds in concatenated receptors. In these constructs the subunits are covalently linked, allowing to form either the α6+/γ2- interface, or the α6+/β3- interface, to study the resulting modulation. With this approach we were able to ascribe the nanomolar modulation to the α6+/γ2- interface. While not all compounds display the nanomolar phase, the strong modulation at the α6+/β3 interface proved to be tolerant for all tested R7 groups. This provides the future option to introduce e.g. isotope labelled or fluorescent moieties or substituents that enhance solubility and bioavailability.

Design and Synthesis of Novel Deuterated Ligands Functionally Selective for the γ-Aminobutyric Acid Type A Receptor (GABAAR) α6 Subtype with Improved Metabolic Stability and Enhanced Bioavailability

Recent reports indicate that α6β2/3γ2 GABAAR selective ligands may be important for the treatment of trigeminal activation-related pain and neuropsychiatric disorders with sensori-motor gating deficits. Based on 3 functionally α6β2/3γ2 GABAAR selective pyrazoloquinolinones, 42 novel analogs were synthesized, and their in vitro metabolic stability and cytotoxicity as well as their in vivo pharmacokinetics, basic behavioral pharmacology, and effects on locomotion were investigated. Incorporation of deuterium into the methoxy substituents of the ligands increased their duration of action via improved metabolic stability and bioavailability, while their selectivity for the GABAAR α6 subtype was retained. 8b was identified as the lead compound with a substantially improved pharmacokinetic profile. The ligands allosterically modulated diazepam insensitive α6β2/3γ2 GABAARs and were functionally silent at diazepam sensitive α1β2/3γ2 GABAARs, thus no sedation was detected. In addition, these analogs were not cytotoxic, which render them interesting candidates for treatment of CNS disorders mediated by GABAAR α6β2/3γ2 subtypes.

LIGANDS SELECTIVE TO ALPHA 6 SUBUNIT-CONTAINING GABAA RECEPTORS ANS THEIR METHODS OF USE

Provided herein are novel pyrazoloquinolinone compounds and method of using such compounds to treat disorders such as neuropsychiatric disorders with sensorimotor gating deficits, such as schizophrenia, tic disorders, attention deficit hyperactivity disorder, obsessive compulsive disorder, panic disorder, Huntington's disease and nocturnal enuresis;depression; temporomandibular myofascial pain; disorders of trigeminal nerve, such as trigeminal neuralgia and trigeminal neuropathy; migraine; and tinnitus.

Synthesis and screening of triazolopyrimidine scaffold as multi-functional agents for Alzheimer's disease therapies

In present study a series of triazolopyrimidine-quinoline and cyanopyridine-quinoline hybrids were designed, synthesized and evaluated as acetylcholinesterase inhibitors (AChEIs). Molecular docking and scoring was utilized for the design of inhibitors. The molecules were synthesized via an easily accessible, convergent synthetic route. Three triazolopyrimidine based compounds showed nanomolar activity towards acetylcholinesterase. Among them, Ethyl 6-fluoro-4-(4-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)piperazin-1-yl)quinoline-3-carboxylate (10d), strongly inhibited AChE with IC50 value of 42 nM. Furthermore compound 10d was identified as most promising compound with 12 fold selectivity against butyrylcholinesterase (BuChE). This compound displayed a composed multitargeted profile with promising inhibition of self-induced and AChE - induced Aβ aggregation and antioxidant activity.

Lead optimization of 3-carboxyl-4(1 H)-quinolones to deliver orally bioavailable antimalarials

Malaria is a protozoal parasitic disease that is widespread in tropical and subtropical regions of Africa, Asia, and the Americas and causes more than 800,000 deaths per year. The continuing emergence of multidrug-resistant Plasmodium falciparum drives the ongoing need for the development of new and effective antimalarial drugs. Our previous work has explored the preliminary structural optimization of 4(1H)-quinolone ester derivatives, a new series of antimalarials related to the endochins. Herein, we report the lead optimization of 4(1H)-quinolones with a focus on improving both antimalarial potency and bioavailability. These studies led to the development of orally efficacious antimalarials including quinolone analogue 20g, a promising candidate for further optimization.

QUINOLINE DERIVATIVES AS CASPASE-3 INHIBITOR, PREPARATION PROCESS FOR THE SAME AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

Provided is a quinoline derivative represented by the following Formula (1) for use in treating a caspase- mediated disease by inhibition of caspase-3 activity. Further provided are a method for preparing the quinoline derivative or a pharmaceutically acceptable salt thereof and a pharmaceutical composition containing the same.

ANTAGONISTS OF THE TRPV1 RECEPTOR AND USES THEREOF

The present application is directed to compounds that are TRPV1 antagonists and have formula (I) wherein variables Ar1, L1, R1, R2, R3, R4, R5, Y1, Y2, and Y3, are as defined in the description, which are useful for treating disorders caused by or exacerbated by vanilloid receptor activity.

Chromanylurea compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor and uses thereof

Compounds that are antagonists of the VR1 receptor, having formula (I) [image] or a pharmaceutically acceptable salt, prodrug, or salt of a prodrug thereof, wherein A1, A2, A3, A4, R7, R8, R9, X, Y, Z, L, n, and m, are as defined herein, and are useful in disorders prevented or ameliorated by inhibiting the VR1 receptor.

Quinolines as extremely potent and selective PDE5 inhibitors as potential agents for treatment of erectile dysfunction

In a continuing effort to discover novel chemotypes as potent and selective PDE5 inhibitors for the treatment of male erectile dysfunction (ED), we have found that 4-benzylaminoquinoline derivatives are very potent and selective PDE5 inhibitors. Some compounds in this series had PDE5 IC 50's as low as 50 pM. While an electron withdrawing group at the C6-position of the quinoline substantially improved PDE5 potency, an ethyl group at the C8-position not only improved the PDE5 potency but also the isozyme selectivity. Substitutents at the C3-position can incorporate a variety of different groups. The synthesis and primary structure-activity relationship of this new series of potent PDE5 inhibitors are described.

Synthesis and SAR of bicyclic heteroaryl hydroxamic acid MMP and TACE inhibitors

Potent and selective bicyclic heteroaryl hydroxamic acid MMP and TACE inhibitors were synthesized by a novel convergent route. Selectivity and efficacy versus MMPs and TACE could be controlled by appropriate substitution on the scaffolds and by variation of the P1′ group. Select compounds were found to be effective in in vivo models of arthritis.