187386-90-9Relevant articles and documents
Green and Efficient Synthesis of 4-Heteryl-Quinolines and Their Antibacterial Evaluations
Bhupathi, Raja S.,Bandi, Madhu,Ch, Venkata Ramana Reddy,Rama Devi,Dubey
, p. 1236 - 1241 (2017)
A green and efficient synthesis of 4-heteryl-quinolines (9a, 9b, 9c, 9d), (10a, 10b, 10c, 10d) and (11a, 11b, 11c, 11d) has been described using PEG-600 as a green solvent. Initially, 4-chloro-2-methylquinolines (5a, 5b, 5c, 5d) on reaction with aromatic heterocyclic thiols (6), (7), and (8) using PEG-600 at 100°C for 30–40 min resulted in (9), (10), and (11) in good yields. Alternatively, (9), (10), and (11) could also be prepared in dimethylformamide using K2CO3 as base and tetrabutylammonium bromide as phase transfer catalyst at 100°C for 1–2 h. All the compounds were synthesized and characterized by IR, NMR, mass spectroscopy, and 13C NMR analysis. All synthesized compounds were screened for their antibacterial activity against clinical strains that include Gram-positive (Bacillus subtilis MTCC 121, staphylococcus aureus MLS-16 MTCC 2940, Micrococcus lutes MTCC 2470, and Staphylococcus aureus MTCC 96) and Gram-negative bacteria (Candida albicans MTCC 3017, Klebsiella planticola MTCC 530, Escherichia coli MTCC 739, and Pseudomonas aeruginosa MTCC 2453). The results revealed that compounds (9a, 9d, 10a, 10c, 11b, and 11d) exhibited significant antibacterial activity almost equal to the standard drug, that is, Ciprofloxacin.
Discovery, synthesis, and optimization of antimalarial 4(1 H)-quinolone-3-diarylethers
Nilsen, Aaron,Miley, Galen P.,Forquer, Isaac P.,Mather, Michael W.,Katneni, Kasiram,Li, Yuexin,Pou, Sovitj,Pershing, April M.,Stickles, Allison M.,Ryan, Eileen,Kelly, Jane Xu,Doggett, J. Stone,White, Karen L.,Hinrichs, David J.,Winter, Rolf W.,Charman, Susan A.,Zakharov, Lev N.,Bathurst, Ian,Burrows, Jeremy N.,Vaidya, Akhil B.,Riscoe, Michael K.
, p. 3818 - 3834 (2014/05/20)
The historical antimalarial compound endochin served as a structural lead for optimization. Endochin-like quinolones (ELQ) were prepared by a novel chemical route and assessed for in vitro activity against multidrug resistant strains of Plasmodium falciparum and against malaria infections in mice. Here we describe the pathway to discovery of a potent class of orally active antimalarial 4(1H)-quinolone-3-diarylethers. The initial prototype, ELQ-233, exhibited low nanomolar IC50 values against all tested strains including clinical isolates harboring resistance to atovaquone. ELQ-271 represented the next critical step in the iterative optimization process, as it was stable to metabolism and highly effective in vivo. Continued analoging revealed that the substitution pattern on the benzenoid ring of the quinolone core significantly influenced reactivity with the host enzyme. This finding led to the rational design of highly selective ELQs with outstanding oral efficacy against murine malaria that is superior to established antimalarials chloroquine and atovaquone.
4-Substituted Thioquinolines and Thiazoloquinolines: Potent, Selective, and Tween-80 invitro Dependent Families of Antitubercular Agents with Moderate invivo Activity
Escribano, Jaime,Rivero-Hernandez, Cristina,Rivera, Hilda,Barros, David,Castro-Pichel, Julia,Perez-Herran, Esther,Mendoza-Losana, Alfonso,Angulo-Barturen, Inigo,Ferrer-Bazaga, Santiago,Jimenez-Navarro, Elena,Ballell, Lluis
experimental part, p. 2252 - 2263 (2012/04/23)
Two new families of closely related selective, non-cytotoxic, and potent antitubercular agents were discovered: thioquinolines and thiazoloquinolines. The compounds were found to possess potent antitubercular properties invitro, an activity that is dependent on experimental conditions of MIC determination (resazurin test and the presence or absence of Tween-80). To clarify the therapeutic potential of these compound families, a medicinal chemistry effort was undertaken to generate a lead-like structure that would enable murine efficacy studies and help elucidate the invivo implications of the invitro observations. Although the final compounds showed only limited levels of systemic exposure in mice, modest levels of efficacy invivo at nontoxic doses were observed. Two new families: In this work we identified two new classes of potent antitubercular agents. Synthesis and analysis of the pharmacological properties of several analogues led to the discovery of potent and selective derivatives invitro, with moderate invivo activity.
