Synthesis, Antiproliferative, and Antioxidant Evaluation of 2-Pentylquinazolin-4(3H)-one(thione) Derivatives with DFT Study

Abstract

The current study was chiefly designed to examine the antiproliferative and antioxidant activities of some novel quinazolinone(thione) derivatives 6–14. The present work focused on two main points; firstly, comparing between quinazolinone and quinazolinthione derivatives. Whereas, antiproliferative (against two cell lines namely, HepG2 and MCF-7) and antioxidant (by two methods; ABTS and DPPH) activities of the investigated compounds, the best quinazolinthione derivatives were 6 and 14, which exhibited excellent potencies comparable to quinazolinone derivatives 5 and 9, respectively. Secondly, we compared the activity of four series of Schiff bases which included the quinazolinone moiety (11a–d). In addition, the antiproliferative and antioxidant activities of the compounds with various aryl aldehyde hydrazone derivatives (11a–d) analogs were studied. The compounds exhibited potency that increased with increasing electron donating group in p-position (OH > OMe > Cl) due to extended conjugated systems. Noteworthy, most of antiproliferative and antioxidant activities results for the tested compounds are consistent with the DFT calculations.

Design, Synthesis, Antibacterial Activity, Antiviral Activity, and Mechanism of Myricetin Derivatives Containing a Quinazolinone Moiety

“…Intermediate c was obtained by reacting substituted anthranilic acid with formamide at 135 °C for 3−6 h. Intermediates b and c were reacted in N,N-dimethylformamide with NaH at 90 °C for 4−6 h to obtain the target compounds. The structures of L1−L20 were characterized by 1 H nuclear magnetic resonance (NMR), 13 C NMR, 19 F NMR, and high-resolution mass spectrometry (HRMS), and the detailed data was included in the Supporting Information.…”

“…The melting point was determined under an X-4B microscope melting point apparatus (Shanghai Yi Dian Physical Optics Instrument Co., Ltd., China). The 1 H, 13 C, and 19 F NMR spectra of the target compounds were obtained on a JEOL-ECX500 MHz (JEOL, Tokyo, Japan). High-resolution mass spectra (HRMS) were procured with a Thermo Scientific Q Exactive (Thermo, Missouri).…”

“…Extraction and purification of TMV; synthetic procedures of target compounds; and characterization data and spectra, including 1 H, 13 C, 19…”

“…Quinazolinone is an important class of nitrogen-containing heterocyclic compounds, whose skeleton is composed of benzene and pyrimidine, and widely exists in a variety of natural alkaloids, such as luotonin F and febrifugine (Figure ). , A number of studies have shown that quinazolinone derivatives have anticancer, antioxidant, antibacterial, antitumor, and other pharmacological activities. In recent years, quinazolinones have gradually attracted the attention of scholars in the creation of new pesticides.…”

Synthesis and Characterization of Some New Quinoxalin-2(1H)one and 2-Methyl-3H-quinazolin-4-one Derivatives Targeting the Onset and Progression of CRC with SAR, Molecular Docking, and ADMET Analyses

“…Quinoxaline and quinazoline and their derivatives are considered as important synthetic targets in anticancer drug discovery [ 19 , 20 , 21 , 22 , 23 , 24 ]. Quinazoline derivatives have been reported to exhibit cytotoxic activity against different cancer types via various mechanisms, including the inhibition of; epidermal growth factor receptor (EGFR) [ 25 ], or kinesin spindle protein (KSP) [ 26 ], interfering with: Wnt signaling pathway [ 27 ] and phosphatidylinositol-3-kinase (PI3K) [ 28 ], in addition to the downregulation of the antiapoptotic proteins Bcl2 and BclxL [ 29 ].…”