5855-56-1

Usage

InChI:InChI=1/C15H10ClN/c16-15-10-13(11-6-2-1-3-7-11)12-8-4-5-9-14(12)17-15/h1-10H

Upstream product

• 5855-57-2 4-phenyl-quinolin-2-ol 
• 5855-57-2 4-phenyl-2-quinolinone 
• 85-99-4 2-acetamidobenzophenone 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 62-53-3 aniline 
• 5652-09-5 2-chloro-4-iodoquinoline 
• 98-80-6 phenylboronic acid 
• 64097-92-3 2-(1-phenylvinyl)aniline 
• 536-74-3 phenylacetylene 
• 605-03-8 4-phenylquinoline 
• 5659-34-7 4-phenylquinoline 1-oxide 
• 100-58-3 phenylmagnesium bromide 
• 551-93-9 2-aminoacetophenone 
• 52744-71-5 1-(2-aminophenyl)-1-phenylethan-1-ol 

Downstream Products

• 72320-59-3 2-(4-ethyl-1-piperazinyl)-4-phenylquinoline 
• 97634-00-9 2-(bromomethyl)-4-phenylquinoline 
• 97634-01-0 4-phenyl-2-<(N,N-diethylamino)methyl>quinoline 
• 97634-03-2 4-(ω-chloropropyl)-1-(4-phenyl-2-quinolyl)piperazine 
• 97634-05-4 2-<3<4<2-(4-phenylquinolyl)>-1-piperazinyl>propyl>-1,2,4-triazolo<4,3-a>pyridine-3<2H>-one 
• 76093-53-3 2-(4-Allyl-piperazin-1-yl)-4-phenyl-quinoline 
• 76093-57-7 2-(4-Benzyl-piperazin-1-yl)-4-phenyl-quinoline 
• 76093-55-5 2-(4-butyl-piperazin-1-yl)-4-phenyl-quinoline 
• 348133-60-8 9-{4-[4-(4-phenyl-quinolin-2-yl)-piperazin-1-yl]-butyl}-9H-fluorene-9-carboxylic Acid-(2,2,2-trifluoro-ethyl)-amide 
• 1269612-34-1 2-butyl-N₄,N₆-bis(4-phenylquinolin-2-yl)pyrimidine-4,6-diamine 
• 1269612-32-9 N₄-(4-phenylquinolin-2-yl)-2-propylpyrimidine-4,6-diamine 
• 1269612-33-0 N₄,N₆-bis(4-phenylquinolin-2-yl)-2-propylpyrimidine-4,6-diamine 
• 1269612-35-2 N₂,N₄-bis(4-phenylquinolin-2-yl)-6-isopropyl-1,3,5-triazine-2,4-diamine 
• 1087269-19-9 4-(4-phenylquinolin-2-yl)phenol 

Relevant academic research and scientific papers

PEG-400 as a carbon synthon: Highly selective synthesis of quinolines and methylquinolines under metal-free conditions

A metal-free, peroxide-free, and efficient procedure for the highly selective synthesis of quinolines and methylquinolines was reported. The main feature of this method was that the same substrate can produce quinolines and methylquinolines, respectively, under different reaction conditions. PEG-400 was used as both a reactant and solvent in this reaction. The utility of the designed procedure was also demonstrated by the derivatization of the products to bioactive compounds. This journal is

Computational and Synthetic approach with Biological Evaluation of Substituted Quinoline derivatives as small molecule L858R/T790M/C797S triple mutant EGFR inhibitors targeting resistance in Non-Small Cell Lung Cancer (NSCLC)

New substituted quinoline derivatives were designed and synthesized via a five-step modified Suzuki coupling reaction. A comparative molecular docking study was carried out on two different types of EGFR enzymes which include wild-type (PDB: 4I23) and T790M mutated (PDB: 2JIV) respectively. Compounds were also validated upon T790M/C797S mutated (PDB ID: 5D41) EGFR enzyme at the allosteric binding site. All docking studies confirmed high potency and flexibility towards wild type as well as a mutated enzyme. Anticancer activity of the synthesized derivatives was examined against HCC827, H1975 (L858R/T790M/C797S and L858R/T790M), A549, and HT-29 cell lines by standard MTT assay. Most of the quinoline derivatives revealed a significant cytotoxic effect. The IC50 values of 4-(4-methylquinolin-2-yl)phenyl 4-(chloromethyl)benzoate (5j) were found to be 0.0042 μM, 0.02 μM, 1.91 μM, 3.82 μM and 3.67 μM while IC50 values of osimertinib were 0.0040 μM, 0.02 μM, ND, 0.99 μM and 1.22 μM, respectively. Compound 5j has shown excellent inhibitory activities against EGFR kinases triple mutant with IC 50 value 1.91 μM. It was observed that, compared to H1975, A549 and A431 cell lines, synthesized compounds significantly inhibited proliferation of the HCC827 cell line. These data suggested that synthesized compounds showed promising selective anticancer activity against tumor cells harboring EGFR Del E746-A750. The potency of compound 5j was compared through molecular dynamic simulations and an insilico ADMET study. QSAR models were generated and the best model was correctly compared with respect to predicted and observed activity of compounds. The built model will assist to design, refine and construct novel substituted quinoline derivatives as potent EGFR inhibitors in near future.

Free energy perturbation guided Synthesis with Biological Evaluation of Substituted Quinoline derivatives as small molecule L858R/T790M/C797S mutant EGFR inhibitors targeting resistance in Non-Small Cell Lung Cancer (NSCLC)

Two different schemes of novel substituted quinoline derivatives were designed and synthesized via simple reaction steps and conditions. A comparative molecular docking study was carried out on two different types of EGFR enzymes which include wild-type (PDB: 4I23) and T790M mutated (PDB: 2JIV) respectively. Compounds were also validated upon T790M/C797S mutated (PDB ID: 5D41) EGFR enzyme at the allosteric binding site. Free energy perturbations were carried out to determine the absolute binding free energy of a protein–ligand complex in the form of ΔGbinding, which in turn provided 4ab and 5ad as the most potential contenders through the structural enhancement in the determined initial scaffolds. Anticancer activity of the synthesized derivatives was examined against HCC827, H1975 (L858R/T790M), A549, and HT-29 cell lines by standard MTT assay. Compound 4ad (6-chloro-2-(isoindolin-2-yl)-4-methylquinoline) has shown excellent inhibitory activities against mutant EGFR kinase with IC50 value 0.91 μM. The potency of compounds 4ab, 4ad and 5ad was compared through an insilico ADMET study.

A Facile Synthesis of 5-Phenyl-Dibenzo[b, g][1,8]Napthyridines

The Vilsmeier Haack heterocyclization of 2-aryl amino-4-phenyl quinolines quinoline yielded the hitherto unknown 5-phenyl-dibenzo[b,g][1,8]naphthyridines in quantitative yield. The synthesis of aryl amines was achieved by the action of anilines on 2-chloro-4-phenyl quinoline, which in turn was sourced through the combes reaction of benzoyl acetanilides.

Lactamization of sp2C?H Bonds with CO2: Transition-Metal-Free and Redox-Neutral

The first direct use of carbon dioxide in the lactamization of alkenyl and heteroaryl C?H bonds to synthesize important 2-quinolinones and polyheterocycles in moderate to excellent yields is reported. Carbon dioxide, a nontoxic, inexpensive, and readily available greenhouse gas, acts as an ideal carbonyl source. Importantly, this transition-metal-free and redox-neutral process is eco-friendly and desirable for the pharmaceutical industry. Moreover, these reactions feature a broad substrate scope, good functional group tolerance, facile scalability, and easy product derivatization.

Beyond a Protecting Reagent: DMAP-Catalyzed Cyclization of Boc-Anhydride with 2-Alkenylanilines

A novel rapid synthesis of quinolines from 2-alkenylanilines has been described; the reaction involves an unexpected DMAP-catalyzed cyclization of 2-alkenylanilines with di-tert-butyl dicarbonate (Boc2O, 2.0 equiv), and a series of tert-butyl quinolin-2-yl carbonate with various functional groups have been synthesized in good yields under mild conditions. Furthermore, the tert-butyl quinolin-2-yl carbonate can be easily converted into corresponding quinolinones and 2-(pseudo)haloquinolines.

INDOLOACRIDINE-CONTAINING DERIVATIVE, PREPARATION PROCESS AND USE THEREOF, AND ORGANIC LUMINESCENT DEVICE

The disclosure provides an indoloacridine-containing derivative represented by formula (I), wherein A is a group represented by formula (II), and wherein X, Y, Z and W represent a carbon atom or a nitrogen atom, and at least one of W, X, Y and Z represent a nitrogen atom; R represents a phenyl group, a biphenylyl group, a naphthyl group or a phenanthryl group. The disclosure further provides a process for preparing the compound. The disclosure further provides an organic electroluminescent device comprising the compound. This compound can be used as a phosphorescence host material, a hole-injecting material or a hole-transporting material in an organic electroluminescent device.

Synthesis of diheteroarylamine ligands by palladium-catalyzed mono- and diamination of dichloroheteroarenes with heteroarenamines

The syntheses of bidentate (see 6 and 12), bis-bidentate (7, 10, and 13) up to oligo-bidentate (see 11 and 14) diheteroarylamine-based N,N-ligands are reported (Tables 2, 4, and 5). In the course of investigations on heteroaromatic (C-N)-bond formations,

Synthesis and anticonvulsant activity of 5-phenyl-[1,2,4]-triazolo[4,3-a] quinolines

A series of novel 5-phenyl-[1,2,4]-triazolo[4,3-a]quinoline derivatives was synthesized by the cyclization of 2-chloro-4-phenyl-1,2-dihydronaphthalene with formohydrazide. The starting material 2-chloro-4-phenyl-1,2-dihydronaphthalene was synthesized from ethyl-3-oxo-3-phenylpropanoate and substituted aniline. Their anticonvulsant activities were evaluated by the maximal electroshock (MES) test and their neurotoxicity was evaluated by the rotarod neurotoxicity test (Tox). The maximal electroshock test showed that 7-hexyloxy-5-phenyl-[1,2,4]- triazolo[4,3-a]quinoline 4f was found to be the most potent compound with an ED50 value of 6.5 mg/kg and a protective index (PI = ED 50/TD50) value of 35.1, which was much higher than the PI of the reference drug phenytoin.

MEDICINAL USE OF RECEPTOR LIGANDS

Compounds of formula (I) are ligands of the melanin concentrating hormone-1 receptor (MCH-1 R), useful in the treatment of diseases responsive to modulation of melanin concentrating hormone (MCH) activity, for example feeding disorders and diseases for which obesity is a risk factor (I): wherein ring B is selected from specific substituted phenyl or benz-fused 5-membered N-containing heterocycles defined in the specification; R, is attached to a ring carbon of ring B, and represents hydrogen, F, Cl, or -OCH3; X is =CH- or =N-; L, is -CH2- or -CH2CH2- ; L2 is a bond, -CH2- or -CO-; R2 is H or C,-C3 alkyl, or -N(R2) L,- is selected from specific cyclic amino linker radicals as defined in the specification; ring A is selected from specific N- containing heterocyclic rings as defined in the specification.