28668-58-8

Usage

Uses

Used in Pharmaceutical Industry:
2-CHLORO-1-(3,4-DIHYDRO-2H-QUINOLIN-1-YL)-ETHANONE is used as a key intermediate in the synthesis of pharmaceuticals for its ability to be incorporated into the molecular structures of various drugs. The presence of the chloro group and the quinoline ring allows for the creation of a wide range of chemical products with potential therapeutic effects.
Used in Agrochemical Industry:
In the agrochemical sector, 2-CHLORO-1-(3,4-DIHYDRO-2H-QUINOLIN-1-YL)-ETHANONE is utilized as a building block in the development of agrochemicals, such as pesticides and herbicides. Its chemical properties make it suitable for the production of compounds that can effectively control, repel, or kill pests and unwanted plant species.
Used in Medicinal Chemistry Research:
2-CHLORO-1-(3,4-DIHYDRO-2H-QUINOLIN-1-YL)-ETHANONE is employed as a research compound in medicinal chemistry for exploring its biological activity. 2-CHLORO-1-(3,4-DIHYDRO-2H-QUINOLIN-1-YL)-ETHANONE's structure offers opportunities for the design and development of new pharmaceutical agents with potential applications in treating various diseases and conditions.

InChI:InChI=1/C11H12ClNO/c12-8-11(14)13-7-3-5-9-4-1-2-6-10(9)13/h1-2,4,6H,3,5,7-8H2

Upstream product

• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 480-73-9 1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline 

Relevant academic research and scientific papers

Novel selective ido1 inhibitors with isoxazolo[5,4-d]pyrimidin-4(5h)-one scaffold

Indoleamine 2,3-dioxygenase 1 (IDO1) is a promising target in immunomodulation of several pathological conditions, especially cancers. Here we present the synthesis of a series of IDO1 inhibitors with the novel isoxazolo[5,4-d]pyrimidin-4(5H)-one scaffold. A focused library was prepared using a 6-or 7-step synthetic procedure to allow a systematic investigation of the structure-activity relationships of the described scaffold. Chemistry-driven modifications lead us to the discovery of our best-in-class inhibitors possessing p-trifluoromethyl (23), p-cyclohexyl (32), or p-methoxycarbonyl (20, 39) substituted aniline moieties with IC50 values in the low micromolar range. In addition to hIDO1, compounds were tested for their inhibition of indoleamine 2,3-dioxygenase 2 and tryptophan dioxygenase, and found to be selective for hIDO1. Our results thus demon-strate a successful study on IDO1-selective isoxazolo[5,4-d]pyrimidin-4(5H)-one inhibitors, defining promising chemical probes with a novel scaffold for further development of potent small-molecule immunomodulators.

Novel gpr120 agonists with improved pharmacokinetic profiles for the treatment of type 2 diabetes

GPR120 is a promising target for the treatment of type 2 diabetes (T2DM), which is activated by free fatty acids (FFAs) and stimulates the release of glucagon-like peptide-1(GLP-1). GLP-1, as an incretin, can enhance glucose-dependent secretion of insulin from pancreatic beta cells and reduce blood glucose. In this study, a series of novel GPR120 agonists were designed and synthe-sized to improve the stability and hydrophilicity of the phenylpropanoic acid GPR120 agonist TUG-891. Compound 11b showed excellent GPR120 agonistic activity and pharmacokinetic properties, and could reduce the blood glucose of normal mice in a dose-dependent manner. In addition, no hypoglycemic side effects were observed even at a dose of 100 mg/kg. Moreover, 11b showed good anti-hyperglycemic effects in diet-induced obese (DIO) mice. Molecular simulation illustrated that compound 11b could enter the active site of GPR120 and interact with ARG99. Taken together, the results indicate that compound 11b might be a promising drug candidate for the treatment of T2DM.

METHOD FOR CONTROLLING HEMATOPHAGOUS OR SAP-FEEDING ARTHROPODS

Modulation of inward potassium ion conductance with structurally diverse small-molecules in the arthropod salivary gland induces arthropod salivary gland failure that results in a reduction or elimination in the ability of the arthropod to feed. Administering Kir channel inhibitors reduces food intake, increases feeding time, reduces salivary gland secretion, induces mortality, and reduces transmission of vector-borne pathogens. Kir channel inhibitors induce these adverse effects in ticks, mosquitoes, horn flies, and aphids.

METHOD FOR PRODUCING TRICYCLIC HETEROCYCLIC COMPOUND

It is an object of the present invention to provide a method for producing a high-purity tricyclic heterocyclic compound represented by formula (I), which is useful as a production intermediate for a pharmaceutical agent, wherein the method is an efficient production method with short steps and with a high yield, which does not use, as raw materials, expensive bromopyruvate and highly harmful copper chromite, and does not need silica gel column chromatography that generates, as by-products, large quantities of waste. The present invention relates to production of Compound (I) by the following method.

One-pot synthesis of indolo[2,3-c]quinolin-6-ones by sequential photocyclizations of 3-(2-azidophenyl)-N-phenylacrylamides

A one-pot synthesis of indolo[2,3-c]quinolin-6(7H)-ones was achieved by sequential photocyclizations of 3-(2-azidophenyl)-N-phenylacrylamides in moderate to high yields. The reactions proceeded via photochemical cyclization of aryl azides to form N-phenylindol-2-carbamides and subsequent 6π-electrocyclic reaction and oxidative aromatization to afford the corresponding indolo[2,3-c]quinolin-6(7H)-ones. Georg Thieme Verlag Stuttgart · New York.

Discovery of novel N -phenylphenoxyacetamide derivatives as EthR inhibitors and ethionamide boosters by combining high-throughput screening and synthesis

In this paper, we describe the screening of a 14640-compound library using a novel whole mycobacteria phenotypic assay to discover inhibitors of EthR, a transcriptional repressor implicated in the innate resistance of Mycobacterium tuberculosis to the second-line antituberculosis drug ethionamide. From this screening a new chemical family of EthR inhibitors bearing an N-phenylphenoxyacetamide motif was identified. The X-ray structure of the most potent compound crystallized with EthR inspired the synthesis of a 960-member focused library. These compounds were tested in vitro using a rapid thermal shift assay on EthR to accelerate the optimization. The best compounds were synthesized on a larger scale and confirmed as potent ethionamide boosters on M. tuberculosis-infected macrophages. Finally, the cocrystallization of the best optimized analogue with EthR revealed an unexpected reorientation of the ligand in the binding pocket.

COMPOUNDS FOR MODULATING TRPV3 FUNCTION

The present application relates to compounds and methods for treating pain and other conditions related to TRP V3.

COMPOUNDS FOR MODULATING TRPV3 FUNCTION

The present application relates to compounds and methods for treating pain and other conditions related to TRPV3.

Indoline and piperazine containing derivatives as a novel class of mixed D2/D4 receptor antagonists. Part 1: Identification and structure-activity relationships

Optimization of the lead compound 2-[-4-(4-chloro-benzyl)-piperazin-1-yl]-1-(2,3-dihydro-indol-1-yl)-ethanone 1 by systematic structure-activity relation (SAR) studies lead to two potent compounds 2-[-4-(4-chloro-benzyl)-piperazin-1-yl]-1-(2-methy-2,3-dihydro-indol-1-yl)- ethanone 2n and 2-[-4-(4-chloro-benzyl)-piperazin-1-yl]-1-(2-methy-2,3-dihydro-indol-1-yl)- ethanone 7b. Their related synthesis was also reported.

Cycloadditions, 9: Intramolecular Diels-Alder Reaction of Allenecarboxanilides; Incorporation of the Amide Nitrogen Atom in Benzo- and Dibenzo-condensated Five-, Six-, and Seven-membered Rings

The allenecarboxanilides 6a-f, the amide nitrogen atom of which is part of a benzo-condensated five-, six-, or seven-membered ring, are synthesized via phosphorus ylides.Thermolysis of 6 in refluxing xylene induces the intramolecular Diels-Alder reaction only in those cases, where the heterocycle is six- or seven-membered.The allenecarboxamide 6b with the six-membered ring bearing only one benzene nucleus in addition furnishes the quinoline derivatives 9 and 10 as main products, while in the case of the allenecarboxamides 6a,c possessing a five-membered heterocycle no reaction takes place whatever.It is tried to explain this different thermolytic behaviour by taking into consideration the spatial arrangement of the two reacting ?-systems (allene and arene) determined by the structure.