Design, Synthesis of Novel 1,2,3‐Triazole Pendent Quinazolinones and Their Cytotoxicity against MCF‐7 Cell Line
Nagaraju Myakala,
Kotaiah Kandula,
Nagamani Rayala
et al.
Abstract:A library of 6‐(((1‐(substitutedphenyl)‐1H‐1,2,3‐triazol‐4‐yl)methyl)amino)‐3‐methylquinazolin‐4(3H)‐one analogues synthesized from Isatin precursor through a series of nitration, reduction, hydrolysis, cyclization and click reaction. The structures of compounds were characterized by spectral data including IR, 1H NMR, 13C NMR and Mass. The novel quinazolinone – 1,2,3‐triazoles were screened for their cytotoxicity against the human breast adenocarcinoma cell lines MCF‐7 by MTT assay. 4‐Isopropyl and 2‐bromo su… Show more
A new series of isatin‐Schiff base linked 1,2,3‐triazole hybrids has been synthesized using CuAAC approach from (E)‐3‐(phenylimino)‐1‐(prop‐2‐yn‐1‐yl)indolin‐2‐one derivatives in high yield (73‐91 %). These synthesized derivatives were characterized using FT‐IR, 1H NMR, 13C NMR, 2D‐NMR and HRMS spectral techniques. The in vitro antimicrobial activity assay proposed that most of the tested hybrids exhibited promising activity. Compound 5j displayed good significant antibacterial efficacy against P. aeruginosa and B. subtilis with MIC value of 0.0062 µmol/mL. While, 5j showed better antifungal potency against A. niger with MIC value of 0.0123 µmol/mL. The docking studies of most promising compounds were also performed with the well‐known antibacterial and antifungal targets i.e. 1KZ1, 5TZ1. Molecular modelling investigations demonstrated that hybrids 5h and 5l exhibited good interactions with 1KZN and 5TZ1, with binding energies of ‐9.6 and ‐11.0 kcal/mol, respectively. Further, molecular dynamics studies of the compounds showing promising binding interactions were also carried out to study the stability of complexes of these hybrids with both the targets.
A new series of isatin‐Schiff base linked 1,2,3‐triazole hybrids has been synthesized using CuAAC approach from (E)‐3‐(phenylimino)‐1‐(prop‐2‐yn‐1‐yl)indolin‐2‐one derivatives in high yield (73‐91 %). These synthesized derivatives were characterized using FT‐IR, 1H NMR, 13C NMR, 2D‐NMR and HRMS spectral techniques. The in vitro antimicrobial activity assay proposed that most of the tested hybrids exhibited promising activity. Compound 5j displayed good significant antibacterial efficacy against P. aeruginosa and B. subtilis with MIC value of 0.0062 µmol/mL. While, 5j showed better antifungal potency against A. niger with MIC value of 0.0123 µmol/mL. The docking studies of most promising compounds were also performed with the well‐known antibacterial and antifungal targets i.e. 1KZ1, 5TZ1. Molecular modelling investigations demonstrated that hybrids 5h and 5l exhibited good interactions with 1KZN and 5TZ1, with binding energies of ‐9.6 and ‐11.0 kcal/mol, respectively. Further, molecular dynamics studies of the compounds showing promising binding interactions were also carried out to study the stability of complexes of these hybrids with both the targets.
Quinazolinone derivatives have garnered attention for their diverse biological activities, including anticancer properties. This review combines findings from 2018 to 2024, focusing on the impact of quinazolinones on cancer cells, tubulin formation, and EGFR/PI3 K pathways. By unraveling the intricacies of structure‐activity relationships, this review endeavors to provide guidance for researchers in identifying promising avenues for the development of cancer treatments. Although in vitro studies underscore significant potential, it is imperative that future research prioritizes pre‐clinical investigations to seamlessly traverse the transitional phase towards clinical applications, thereby propelling the advancement of quinazolinone‐based cancer therapy.
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