Quinazoline-based VEGFR-2 inhibitors as potential anti-angiogenic agents: A contemporary perspective of SAR and molecular docking studies

[Cell@Al2O3(HEPiPY)]DCA: A Cellulose Supported Ionic Liquid Catalyst for Synthesis of 11 b,12‐dihydro‐6H,13Hbenzo[5,6][1,3]oxazino[3,4‐a]quinazoline‐6,13‐dione along with in silico assessments

“…Besides the experimental achievements of this work, the electronic structure features and the biological activities of obtained derivatives were evaluated along with in silico assessments. It is important to mention that the quinazoline derivatives have been supposed to work against the vascular endothelial growth factor receptor-2 (VEGFR-2) target by the results of earlier works, [29][30][31] in which assessing such features for the current derivatives could provide insights into their possible biological applications. VEGFR-2 is an important enzyme in the living systems with hazardous effects in an overexpression state; hence, considerable efforts have been focused on the exploration of novel ligand inhibitors against the VEGFR-2 overactivity up to now.…”

Design, Synthesis, and Biological Evaluation of Novel Quinazoline Derivatives Possessing a Trifluoromethyl Moiety as Potential Antitumor Agents

“…Column chromatography was performed with silica gel 60 (200-300 mesh). 1 H, 13 C, and 19 F NMR spectra were recorded on Bruker AVANCE NEO 600 spectrometer in appropriate deuterated reagents. 1 H and 13 C NMR chemical shifts are reported relative to CDCl 3 (7.26, 77.06 ppm), DMSO-d 6 (2.50 ppm, 39.53 ppm), and CD 3 OD (3.31, 49.03 ppm).…”

“…1 H, 13 C, and 19 F NMR spectra were recorded on Bruker AVANCE NEO 600 spectrometer in appropriate deuterated reagents. 1 H and 13 C NMR chemical shifts are reported relative to CDCl 3 (7.26, 77.06 ppm), DMSO-d 6 (2.50 ppm, 39.53 ppm), and CD 3 OD (3.31, 49.03 ppm). Multiplicity is given as follows: s = singlet, d = doublet, dd = doublet of doublets, t = triplet, q = quartet, and m = multiplet.…”

“…[9] This has made privileged scaffold-based drug discovery a popular strategy in the lead optimization stages of the anti-cancer drug discovery process. [10] The quinazoline [11,12] is a privileged scaffold that has been found in various biologically active natural products and is known to possess many medicinal properties, [13,14] such as antitumor, [15,16] antiviral, [17] antibacterial, [18] and anti-inflammatory [19] properties. In particular, in the field of anti-cancer drug research, the most renowned first and second-generation EGFR inhibitors such as Gefitinib, Erlotinib, and Vandetanib (Figure 1) have been developed and employed with quinazoline as the core skeleton.…”

“…structure of the target compounds, the synthesis route was divided into two parts: the synthesis of the key intermediates 7 a~7 c (Scheme 1), and the coupling reaction of these intermediates with appropriate anilines (Scheme 2~4). All of the synthesized 4-trifluoromethyl quinazoline target compounds and related intermediates were characterized by a combination of 1 H-NMR, 13 C NMR, and 19 F NMR spectra.…”