Design, synthesis, and anti-proliferative evaluation of new quinazolin-4(3H)-ones as potential VEGFR-2 inhibitors

  • Bioorg Med Chem. 2021 Jan 1:29:115872. doi: 10.1016/j.bmc.2020.115872.
Khaled El-Adl  1 Abdel-Ghany A El-Helby  2 Rezk R Ayyad  2 Hazem A Mahdy  2 Mohamed M Khalifa  2 Hamdy A Elnagar  2 Ahmed B M Mehany  3 Ahmed M Metwaly  4 Mostafa A Elhendawy  5 Mohamed M Radwan  6 Mahmoud A ElSohly  7 Ibrahim H Eissa  8
Affiliations
  • 1. Pharmaceutical Medicinal Chemistry & Drug Design Department, Faculty of Pharmacy (Boys), Al-Azhar University, Cairo 11884, Egypt; Pharmaceutical Chemistry Department, Faculty of Pharmacy, Heliopolis University for Sustainable Development, Cairo, Egypt. Electronic address: [email protected].
  • 2. Pharmaceutical Medicinal Chemistry & Drug Design Department, Faculty of Pharmacy (Boys), Al-Azhar University, Cairo 11884, Egypt.
  • 3. Zoology Department, Faculty of Science, Al-Azhar University, Cairo 11884, Egypt.
  • 4. Pharmacognosy Department, Faculty of Pharmacy (Boys), Al-Azhar University, Cairo 11884, Egypt.
  • 5. Department of Agriculture Chemistry, Faculty of Agriculture, Damietta University, Damietta, Egypt; National Center for Natural Products Research, University of Mississippi, MS 38677, USA.
  • 6. National Center for Natural Products Research, University of Mississippi, MS 38677, USA; Department of Pharmacognosy, Faculty of Pharmacy, Alexandria University, Alexandria, Egypt.
  • 7. National Center for Natural Products Research, University of Mississippi, MS 38677, USA; Department of Pharmaceutics and Drug Delivery, University of Mississippi, University, MS 38677, USA.
  • 8. Pharmaceutical Medicinal Chemistry & Drug Design Department, Faculty of Pharmacy (Boys), Al-Azhar University, Cairo 11884, Egypt. Electronic address: [email protected].
Abstract

Inhibiting VEGFR-2 has been set up as a therapeutic strategy for treatment of Cancer. Thus, nineteen new quinazoline-4(3H)-one derivatives were designed and synthesized. Preliminary cytotoxicity studies of the synthesized compounds were evaluated against three human Cancer cell lines (HepG-2, MCF-7 and HCT-116) using MTT assay method. Doxorubicin and sorafenib were used as positive controls. Five compounds were found to have promising cytotoxic activities against all cell lines. Compound 16f, containing a 2-chloro-5-nitrophenyl group, has emerged as the most active member. It was approximately 4.39-, 5.73- and 1.96-fold more active than doxorubicin and 3.88-, 5.59- and 1.84-fold more active than sorafenib against HepG2, HCT-116 and MCF-7 cells, respectively. The most active cytotoxic agents were further evaluated in vitro for their VEGFR-2 inhibitory activities. The results of in vitro VEGFR-2 inhibition were consistent with that of the cytotoxicity data. Molecular docking of these compounds into the kinase domain, moreover, supported the results.

Keywords
Anticancer; Molecular docking; Quinazolin-4(3H)-one; VEGFR-2.