Design and synthesis of some novel quinoline derivatives as anticancer and radiosensitizing agents targeting VEGFR tyrosine kinase

Khanna

Journal of Heterocyclic Chem

et al. 2017

A series of some substituted diethyl 4‐(2‐chloroquinolin‐3‐yl)‐2,6‐dimethylpyridine‐3,5‐dicarboxylates has been synthesized from substituted diethyl4‐(2‐chloroquinolin‐3‐yl)‐1,4‐dihydro‐2,6‐dimethylpyridine‐3,5‐dicarboxylates (1,4‐DHPs) by treating the latter with SiO2–HNO3 which proved to be a better oxidant in terms of product yield, reaction time, and cost. Further, these compounds were screened for their antimicrobial activity. All the diethyl 4‐(2‐chloroquinolin‐3‐yl)‐2,6‐dimethylpyridine‐3,5‐dicarboxylates exhibited more potent activities than the corresponding 1,4‐DHPs. Further, docking simulation of the most active and least active compounds 3e and 2e into Escherichia coli topoisomerase II DNA Gyrase B was also performed.

Section: Introductionmentioning

confidence: 99%

Synthesis of Some 4‐Quinolinyl Pyridines and their Antimicrobial and Docking Studies

Khanna

Journal of Heterocyclic Chem

et al. 2017

“…Pyrazoles and their derivatives exhibit antimicrobial (1-3), anticancer (4), antiinflammatory (5) radioprotective (6), anticonvulsant (7) and antimalarial (8) activities. In the light of these facts, and as a continuation of our efforts towards synthesizing biologically active heterocyclic compounds (9)(10)(11)(12)(13)(14)(15)(16)(17)(18), we aimed to prepare new derivatives of pyrazoles. The compounds were designed with the aim of exploring their antimicrobial activity and to study their structure-activity relationship.…”

mentioning

confidence: 99%

Novel Ethyl 1,5-Disubstituted-1H-Pyrazole-3-Carboxylates as a New Class of Antimicrobial Agents

et al. 2014

Self Cite

A series of pyrazole derivatives 9-22 were designed and synthesized. All the newly synthesized compounds were assayed for their antimicrobial activity against the Grampositive bacteria Staphyllococcus aureus and Bacillius subtilis and the Gram-negative bacteria Escherichia coli, Pseudomonas aeruginosa, in addition to the fungi organisms, Candida albicans, C. parapsilosis and C. tropicalis. Ethyl 5-(2,5-dimethylthiophen- 3-yl)-1-phenyl-1H-pyrazole-3-carboxylate (21) (MICE.coli = 0.038 μmol mL-1, MICP. aerug. = 0.067 μmol mL-1) is nearly as active as ampicillin (MIC = 0.033 and 0.067 μmol mL-1), respectively. Ethyl 5-(4-bromo-2-chlorophenyl)- 1-phenyl-1H-pyrazole-3-carboxylate (16) (MIC = 0.015 μmol mL-1) is more active than fluconazole (0.020 μmol mL-1) as a reference drug against C. parapsilosis.

“…[4] When aryl sulfonyl moieties with electron-donating groups are used as N-protecting groups, a Michael/aldol/aromatization cascade proceeds predominantly to give polysubstituted quinolines. However, when sulfonyl moieties with electron-withdrawing groups, such as the triflic group, are employed as N-protecting group, chiral 1,4-dihydroquinolines are produced through a highly enantioselective Michael/aldol cascade reaction.The "privileged" status of quinolines and related chiral hydroquinolines in organic synthesis [5] and biological applications [6] demands more efficient strategies for their preparation. Although classic annulation reactions [7] and new, improved versions [8] have been developed, in general they require multiple steps and/or highly functionalized substrates.…”

mentioning

confidence: 99%

An Organocatalytic Cascade Approach toward Polysubstituted Quinolines and Chiral 1,4‐Dihydroquinolines–Unanticipated Effect of N‐Protecting Groups

Zhang

Song

et al. 2012

Angew Chem Int Ed

A matter of protection: The outcome of a divergent organocatalytic aza-Michael/aldol cascade process toward quinolines and 1,4-dihydroquinolines depends on the choice of the N-protecting group (see scheme; TEA = triethylamine, TMS = trimethylsilyl). Use of an electron-donating sulfonyl group results in an unanticipated aza-Michael/aldol/aromatization cascade to give polysubstituted quinolines (right). In contrast, chiral 1,4-dihydroquinolines are obtained with an electron-withdrawing sulfonyl group (left).