102878-18-2

Usage

Uses

Used in Pharmaceutical Industry:
2,4-DICHLORO-6-METHYLQUINOLINE is used as a chemical intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Agricultural Industry:
2,4-DICHLORO-6-METHYLQUINOLINE is used as a pesticide for its insecticidal properties, helping to control and manage pest populations in agricultural settings.
Used in Medicinal Research:
2,4-DICHLORO-6-METHYLQUINOLINE is used as a subject of study in medicinal research for its potential therapeutic properties, with the aim of discovering new treatments for certain diseases and disorders.

InChI:InChI=1/C10H7Cl2N/c1-6-2-3-9-7(4-6)8(11)5-10(12)13-9/h2-5H,1H3

Upstream product

• 1677-44-7 4-hydroxy-6-methylquinolin-2(1H)-one 
• 141-82-2 malonic acid 
• 106-49-0 p-toluidine 
• 215589-37-0 2-ethynyl-4-methylaniline 
• 503-38-8 trichloromethyl chloroformate 
• 151772-23-5 2,4-Dichloro-6-methyl-quinoline-3-carbaldehyde 
• 1677-44-7 6-methylquinoline-2,4-diol 
• 784183-53-5 2,2,2-trifluoro-N-(2-iodo-4-methylphenyl)acetamide 
• 180624-14-0 4-methyl-2-[2-(trimethylsilyl)ethynyl]aniline 
• 29289-13-2 2-iodo-4-methylaniline 

Downstream Products

• 1228173-78-1 2-[(2-benzoyl-4-chlorophenyl)amino]-4-chloro-6-methylquinoline 
• 1268471-54-0 2,9-dimethyl-7-phenyl-6-(N-(4-methylphenyl)amino)dibenzo[b,h][1,6]naphthyridine 
• 1268471-55-1 6-methyl-2,4-bis(N-(4-methylphenyl)amino)quinoline 
• 18618-02-5 8-chloro-5-methyl-2-phenylquinoline 
• 1094428-49-5 C₁₆H₁₂ClN 
• 73402-92-3 2,4-diphenyl-6-methylquinoline 
• 1424371-16-3 dimethyl 4-(4-(2-chloro-6-methylquinolin-4-yloxy)phenyl)-2,6-dimethyl-1,4-dihydro pyridine-3,5-dicarboxylate 
• 1424371-06-1 diethyl 4-(4-(2-chloro-6-methylquinolin-4-yloxy)phenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 1386328-59-1 ethyl 4-(3-(2-chloro-6-methylquinolin-4-yloxy)phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 141848-59-1 (S)-2-{4-[(2,4-Dichloro-quinolin-6-ylmethyl)-prop-2-ynyl-amino]-2-fluoro-benzoylamino}-pentanedioic acid di-tert-butyl ester 

Relevant academic research and scientific papers

New Quinoline-2-one/thiazolium bromide Derivatives; Synthesis, Characterization and Mechanism of Formation

We report on the formation of new quinoline-2-one derived by thiazolium bromides from the reaction of 3-thiosemicarbazides derived by 2-quinolones with 2-bromoacetophenones. The structure of products was elucidated by mass, IR and NMR spectra together with elemental analysis. The mechanism of products formation was discussed.

Arylidenes of Quinolin-2-one scaffold as Erlotinib analogues with activities against leukemia through inhibition of EGFR TK/ STAT-3 pathways

A new series of 6-substiuted-4-(2-(4-substituted-benzylidene)hydrazinyl)quinolin-2(1H)-one derivatives have been designed and synthesized. The structure of the synthesized compounds was proved by 1H NMR, 13C NMR, 2D NMR, mass and elemental analyses. The target compounds were evaluated for their in vitro cytotoxic activity against 60 cancer cell lines according to NCI protocol. Consequently, the most active compounds were further examined against the most sensitive leukemia RPMI-8226 and on healthy cell lines. 6-Chloro-derivative was the most active one; with IC50 = 15.72 ± 1.21 and 46.05 ± 2.36 μM against RPMI-8226 and normal cell lines, respectively. Also, it showed a remarkable inhibitory activity compared to gefitinib on the EGFR TK mutant, wild and on H-RAS in addition to STAT-3 with IC50 = 695.49 ± 21.8, 263.15 ± 15.13, 10.61 ± 0.27 and 1.753 ± 0.81 nM, respectively. Cell cycle analysis of RPMI-8226 cells treated with the 6-chloro-derivative showed cell cycle arrest at G2/M phase (supported by Caspases-3,8, BAX and Bcl-2 studies) with a significant pro-apoptotic activity as indicated by annexin V-FITC staining. Moreover, the docking studies ROCS analysis and Tanimoto scores supported the results. The study illustrated the effect of several factors on compounds activity.

Identification and molecular modeling of new quinolin-2-one thiosemicarbazide scaffold with antimicrobial urease inhibitory activity

Abstract: A new series of 6-substituted quinolin-2-one thiosemicarbazides 6a–j has been synthesized. The structure of the target compounds was proved by different spectroscopic and elemental analyses. All the designed final compounds were evaluated for their in vitro activity against the urease-producing R. mucilaginosa and Proteus mirabilis bacteria as fungal and bacterial pathogens, respectively. Moreover, all compounds were in vitro tested as potential urease inhibitors using the cup-plate diffusion method. Compounds 6a and 6b were the most active with (IC50 = 0.58 ± 0.15 and 0.43 ± 0.09?μM), respectively, in comparison with lead compound I (IC50 = 1.13 ± 0.00?μM). Also, the designed compounds were docked into urease proteins (ID: 3LA4 and ID: 4UBP) using Open Eye software to understand correctly about ligand–receptor interactions. The docking results revealed that the designed compounds can interact with the active site of the enzyme through multiple strong hydrogen bonds. Moreover, rapid overlay of chemical structures’ analysis was described to understand the 3D QSAR of synthesized compounds as urease inhibitors. The results emphasize the importance of polar thiosemicarbazide directly linked to 6-substituted quinolone moieties as promising antimicrobial urease inhibitors. Graphic abstract: [Figure not available: see fulltext.]

Synthesis, crystal structure, cytotoxic and apoptotic activity of 2,4-dichloro-6-methylquinoline on human oral carcinoma cell line

The present report describes the synthesis, IR spectra, 3-dimensional structure of the compound 2,4-dichloro-6-methylquinoline and evaluation of its anti-cancer activity using propidium iodide (PI) staining and annexin binding assay techniques. This derivative of quinoline was synthesized from the mixture of p-toluidine and malonic acid and synthesis has been achieved in a one-pot reaction from an aryl amine, malonic acid and phosphorous oxychloride. Crystallographic data reveals that the crystals belong to triclinic crystal system with space group P-1 with the unit cell dimensions of a = 7.14(1) A, b = 11.53(1) A, c = 11.97(1) A and α = 90.18° (10), β = 106.31° (10), γ = 91.07° (10). The in vitro anti-cancer assay indicated that compound has cytotoxic and apoptotic activity on human oral squamous carcinoma (KB) cell line, thus it could be developed as a potent anti-cancer agent. Synthesis, Crystal Structure, Cytotoxic and Apoptotic Activity of 2,4-Dichloro-6-methylquinoline on Human Oral Carcinoma Cell Line R. K. Somvanshia, R. Subashinib, V. Dhanasekaranb, G. Arulprakashb, S. N. Dasc, S. Deya [Figure not available: see fulltext.]

Synthesis, characterization, pharmacological, molecular modeling and antimicrobial activity evaluation of novel isomer quinoline derivatives

The structural and spectroscopic characteristics of the synthesized structurally novel compound 4-chloro-6-methylquinoline-2(1H)-one (4C6MQ) and its isomer 4-chloro-8-methylquinoline-2(1H)-one (4C8MQ) have been examined by means of experimental and computational quantum chemical methods like density functional theory (DFT). The crystal structure of the 4C6MQ compound has been brought to light by single-crystal x-ray diffraction (SCXRD) method which consists of two independent molecules (A and B) in the asymmetric unit with similar conformations. Both the isomer compounds are characterized spectroscopically by FTIR, FT-Raman, UV-Vis, and NMR spectrum and compared with DFT results. The geometries of the isomer compounds have been optimized by using DFT/B3LYP method with the 6-311G++(d,p) basis sets. From the optimized geometry of the compounds, geometric parameters (bond lengths, bond angles, and torsion angles); vibrational analysis; chemical shifts; and electronic absorption of the isomer compounds have been computed and compared with the experimental result. The detailed assignments of vibrational wave numbers have been prepared based on potential energy distribution (PED) which was carried out in the VEDA4 program. In addition, natural bonding orbital analysis, frontier molecular orbital, and molecular electrostatic potential have been explained theoretically. The in silico (absorption, distribution, metabolism, excretion and toxicity) studies were analyzed to identify the potential drug likeliness of the isomer compounds. The implications of the inhibitory activity of isomer compounds against DNA gyrase and lanosterol 14 α-demethylase enzyme by molecular docking are discussed. Further, the isomer compounds were screened for their antibacterial and antifungal activities.

Analysis of Cl...Cl and C-H...Cl intermolecular interactions involving chlorine in substituted 2-chloroquinoline derivatives

Six crystal structures of substituted 2-chloroquinoline derivatives have been analysed to evaluate the role of Cl atom as a self recognizing unit resulting in the formation of Cl...Cl and C-H...Cl interactions to generate supramolecular assembly in the solid state. The features of Type I and Type II geometries associated with Cl...Cl interactions have been analysed to show directional preferences leading to differences in the packing motifs in these crystal structures. C-H...Cl interactions are generated exclusively in structures depicting Type II Cl...Cl interaction have been observed in these structures. Indian Academy of Sciences.

A novel rearrangement of 3-arylisoxazol-5(4H)-ones: One-pot synthesis of new 2,4-dichloroquinoline-3-carbaldehydes

Vilsmeier-Haack reaction, using a specific combination of phosphorus oxychloride and dimethylformamide, on 3-arylisoxazol-5(4H)ones 1 resulted in 2,4-dichloroquinoline-3-carbaldehydes 6 as the major products along with other minor products, through a novel rearrangement. Oxidation of 6 with alkaline potassium permanganate gave 2,4-dichloroquinoline-3-carboxylic acids 7. Decarboxylation of 6 and decarboxylation of 7 using aqueous sodium hydroxide yielded 2,4-dichloroquinolines 8. All the compounds were characterised by elemental and spectral analysis.

Synthesis and characterization of substituted 4-methoxy-1H-quinolin-2-ones

An efficient method for the synthesis of various substituted 4- methoxy-1H-quinolin-2-ones from various substituted aniline with malonic acid, phosphorous oxychloride, sodium methoxide and glacial acetic acid under different conditions is described. The title compounds were synthesized from three steps; the first step involved the synthesis of substituted 2, 4-dichloro quinoline from aniline (substituted), with malonic acid and phosphorousoxychloride. In the second step, the substituted 2, 4 dichloro compounds was heated with freshly prepared methanolic sodium methoxide solution to give 2, 4-dimethoxy quinoline compounds, it was then refluxed with glacial acetic acid and hydrochloric acid to give the titled compounds in the final step. The purity of the synthesized compounds was confirmed by their C, H and N analysis and the structure was analyzed on the basics of Mass, FT-IR and 1H NMR.

An efficient click synthesis of chalcones derivatized with two 1-(2-quinolon-4-yl)-1,2,3-triazoles

Chalcones derivatized with 1-(2-quinolonyl)-1,2,3-triazoles were synthesized by reaction of 4-azido-2-quinolones with 1-phenyl-3-(4-propargyloxyphenyl)prop-2-en-1-one, or by aldol reaction of 4-{[1-(2-oxo-1,2-dihydroquinolin-4-yl)-1H-1,2,3-triazol-4-yl]methoxy}benzaldehydes with acetophenone. Whereas, chalcones bearing two 1-(2-quinolonyl)-1,2,3-triazoles were synthesized by reaction of 1,3-bis(4-propargyloxyphenyl)prop-2-en-1-one with 4-azido-2-quinolones, or by aldol condensation between 4-{4-[(4-acetylphenoxy)methyl]-1H-1,2,3-triazol-1-yl}quinolin-2(1H)-ones and 4-{[1-(2-oxo-1,2-dihydroquinolin-4-yl)-1H-1,2,3-triazol-4-yl]methoxy}benzaldehydes.

Novel Pyrazoloquinolin-2-ones: Design, synthesis, docking studies, and biological evaluation as antiproliferative EGFR-TK inhibitors

Two new series of diethyl 2-[2-(substituted-2-oxo-1,2-dihydroquinolin-4-yl)hydrazono]-succinates 6a-g and 1-(2-oxo-1,2-dihydroquinolin-4-yl)-1H-pyrazoles 7a-f have been designed and synthesized. The structures of the synthesized compounds were proved by IR, mass, NMR (2D) spectra and elemental analyses. The target compounds were evaluated for their in vitro cytotoxic activity against 60 cancer cell lines according to NCI protocol. Consequently, seven compounds were further examined against the most sensitive cell lines, leukemia CCRF-CEM, and MOLT-4. 5-Amino-1-(6-bromo-2-oxo-1,2-dihydroquinolin-4-yl)-1H-pyrazole-3,4-dicarbonitrile (7f) was the most active product, with IC50 = 1.35 uM and 2.42 uM against MOLT-4 and CCRF-CEM, respectively. Also, it showed a remarkable inhibitory activity compared to erlotinib on the EGFR TK with IC50 = 247.14 nM and 208.42 nM, respectively. Cell cycle analysis of MOLT-4 cells treated with 7f showed cell cycle arrest at G2/M phase (supported by Caspases, BAX and Bcl-2 studies) with a significant pro-apoptotic activity as indicated by annexin V-FITC staining. Moreover, the docking study indicated that both the pyrazole moiety and the quinolin-2-one ring showed good fitting into EGFR (PDB code: 1M17). In order to interpret SAR of the designed compounds, and provide a basis for further optimization, molecular docking of the synthesized compounds to known EGFR inhibitors was performed. The study illustrated the effect of several factors on the compounds’ activity.