Abstract
Structures containing 8-hydroxyquinoline scaffold are useful for anticancer drug development. The title ester (5-chloroquinolin-8-yl)-2-fluorobenzoate was prepared by the reaction of 2-fluorobenzoyl chloride with 5-chloro-8-hydroxyquinoline. The structure of the title compound was assigned by diverse spectroscopic techniques. Moreover, a crystallographic study was undertaken and its supramolecular characteristics were analyzed. Thus, the central ester fragment C8/O1/C10(O2)/C11 is almost planar with a root mean square (r.m.s.) deviation of 0.0612 Å and it makes dihedral angles of 76.35(6)° and 12.89(11)°, with quinoline and phenyl rings respectively. The structure shows C–H...X (X = halogen) non-classical hydrogen bonds. It also has a halogen…halogen distance less than the sum of the van der Waals radii (3.2171(15) Å). As a result of interactions with halogen atoms, chains of centrosymmetric dimer that form edge-fused R22(18) rings run parallel to the plane (100).
Highlights
The N-heterocycles such as quinolines are important starting pharmacophores for preparing therapeutic agents with a wide spectrum of biological activities, such as antimalarial [1], antiviral [2], antibacterial [3], anti-inflammatory [4], and mainly antitumor [5,6,7] activities
Molbank 2017, 2017, M934 the residue was purified by column chromatography on silica gel using dichloromethane as eluent, Molbank
The residue was purified by column chromatography on silica gel using dichloromethane as eluent, affording a white solid
Summary
The N-heterocycles such as quinolines are important starting pharmacophores for preparing therapeutic agents with a wide spectrum of biological activities, such as antimalarial [1], antiviral [2], antibacterial [3], anti-inflammatory [4], and mainly antitumor [5,6,7] activities. NMR and mass spectrum), formation of the new ester 3 was confirmed. The residue was purified by column chromatography on silica gel using dichloromethane as eluent, affording a white solid. NMR and mass spectrum), new ester 3 was confirmed. 1H-NMR spectrum of the quinoline-derivative 3 recorded at 25 °C in CDCl3 shows nine different was purified by column chromatography on silica gel using dichloromethane as eluent, affording a aromatic protons in the range of 7.22–8.95 ppm and the absence of the phenolic proton signal, which white solid. After analysis by analytical and spectroscopic techniques The mass spectrum, is and 3 is and a known apparently commercial no details about consistent with structure spectroscopic characterization NMR, mass and was performed in work, see Material and Methods section.
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