Synthesis and cytotoxic evaluation of novel quinozalinone derivatives with substituted benzimidazole in position 3

Abstract

Quinazolinone and benzimidazole are both fused heterocyclic compounds which have shown valuable biological properties including cytotoxic, antibacterial, and antifungal activities. In this study, a series of novel quinazolinone derivatives substituted with benzimidazole were synthesized in two parts. In the first part 2 - phenyl - 1 H - benzimidazol - 6 - amine ( 4 ) was synthesized from the reaction of 4-nitro-o-phenylenediamine and benzoic acid. In the second part, new 3-(2-phenyl-1 H benzoimidazol-5-yl)- 3H-quinazolin-4-one derivatives ( 8a-8f ) were also prepared. Finally compound 4 was reacted with the different benzoxazinone derivatives ( 8a-8f ) to give the target compounds. The structures of the synthesized compounds were confirmed by IR and 1 HNMR. Cytotoxic activities of the final compounds were assessed at 100, 200, 300, 400, and 500 μM against MCF-7 and HeLa cell lines using the MTT colorimetric assay. Almost all compounds exhibited good cytotoxic activity against both cell lines. Compound 9d demonstrated the highest cytotoxic activity against MCF7 and Hela cell lines with IC 50 70 μM and 50 μM, respectively.

Synthesis and cytotoxic evaluation of some quinazolinone- 5-(4-chlorophenyl) 1, 3, 4-oxadiazole conjugates

“…reported the synthesis and cytotoxic evaluation of quinazolinone- benzimidazole hybrid derivatives against MCF-7 and HeLa cell lines. Cytotoxicity results revealed that compounds with phenyl and nitrophenyl substitutes on C2 of the quinazolinone ring had the lowest cytotoxic activity against both cell lines and compounds with aliphatic substituents in this position had the highest potency (30). Other hybrids of quinazolinone-triazole were recently reported by Jafari et al .…”

Synthesis and characterization of silica‐coated Fe3O4 nanoparticle@silylpropyl triethylammonium polyoxometalate as an organic–inorganic hybrid heterogeneous catalyst for the one‐pot synthesis of tetrahydrobenzimidazo[2,1‐b]quinazolin‐1(2H)‐ones

“…[32] Very recently, tetrahydrobenzimidazo [2,1-b]quinazolines have been reported to show antioxidant and anticancer activity. [33] In the past three decades, multicomponent reactions (MCRs) have been widely used for the synthesis of organic compounds. [34] In this procedure, the product is simply formed in a single step from starting materials without separation and purification of intermediates from reaction media.…”

“…[ 30 ] Besides, a number of reports exist about fused benzimidazoquinazolines. [ 31–33 ] Benzimidazo[1,2‐c]quinazolines have been used as antimicrobial [ 31 ] and antiviral agents as well as interferon inducers. [ 32 ] Very recently, tetrahydrobenzimidazo[2,1‐ b ]quinazolines have been reported to show antioxidant and anticancer activity.…”

“…[ 32 ] Very recently, tetrahydrobenzimidazo[2,1‐ b ]quinazolines have been reported to show antioxidant and anticancer activity. [ 33 ]…”

Antitumor, cytotoxic, and antioxidant evaluation of six heterocyclic compounds containing different heterocycle moieties

“…Cancer is moving to be a significant health problem in the world . According to a World Health Organization (WHO) report, cancer is the second leading cause of death globally and is responsible for an estimated 9.6 million deaths in 2018 .…”