607-66-9Relevant articles and documents
A facile synthesis of novel 9-methyl[1,2,3]selenadiazoles[4,5-b]quinoline and 9-methyl[1,2,3]thiadiazole[4,5-b]quinoline as a new class of antimicrobial agents
Bhojya Naik, Halehatty S.,Ramesha, Machenahalli S.,Swetha, Boovanahalli V.,Roopa, Thopenahalli R.
, p. 533 - 541 (2006)
2-chloro-4-methyl quinoline 2 on condensation with semicarbazide hydrochloride gave its semicarbazone. This on reaction with SeO2 and SOCl2 yielded a new class of novel selenadiazoles 4 and thiadiazoles 5, respectively. The structure of all the compounds were elucidated on the basis of elemental analysis, IR, 1H NMR, and the mass spectral data. Some derivatives of 9-methyl[1,2,3]selenadiazole[4,5-b] quinoline and 9-methyl[1,2,3]thiadiazole [4,5-b]quinoline have been screened for antimicrobial activities. Copyright Taylor & Francis Group, LLC.
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)
Karnik, Kshipra S.,Sarkate, Aniket P.,Tiwari, Shailee V.,Azad, Rajaram,Burra, Prasad V.L.S.,Wakte, Pravin S.
, (2021/02/05)
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.
Metal-Free C-H [5 + 1] Carbonylation of 2-Alkenyl/Pyrrolylanilines Using Dioxazolones as Carbonylating Reagents
Nan, Jiang,Chen, Pu,Gong, Xue,Hu, Yan,Ma, Qiong,Wang, Bo,Ma, Yangmin
supporting information, p. 3761 - 3766 (2021/05/10)
A novel metal-free C-H [5 + 1] carbonylative annulation of 2-alkenyl/pyrrolylanilines with dioxazolones has been established for the assembly of the privileged quinolinones and pyrrolyl-fused quinoxalinones. Entirely differing from the existing reports, the dioxazolones herein behave with an innovative chemistry and first emerge as carbonylating reagents to participate in annulation reactions. Moreover, this process features exceedingly simple operation (only solvent) and tolerates both vinyl and aryl substrates. Comprehensive mechanistic studies indicate that the formed isocyanate intermediate plays a crucial role in enabling the carbonylation annulation.