Synthesis of Quinazoline‐1,3,4‐Oxadiazole Linked 1,2,3‐Triazole Hybrids as Potent EGFR Targeting Antilung Cancer Agents: In Vitro, In Silico, and DFT Studies DOI

Sampath peddapelli,

Mahadev Bandgar,

Ravikumar Kapavarapu

и другие.

ChemistrySelect, Год журнала: 2025, Номер 10(16)

Опубликована: Апрель 1, 2025

Abstract This research focuses on the design and synthesis of novel quinazoline‐1,3,4‐oxadiazole linked 1,2,3‐triazoles. Subsequently, it investigates their in vitro inhibitory effects EGFR kinases anticancer efficacy against lung cancer cell lines A‐549 H1299. Compared to primary compound, erlotinib, most tested compounds demonstrated superior efficacy. The 2‐(((1‐(3,5‐difluorophenyl)‐1 H ‐1,2,3‐triazol‐4‐yl)methyl)sulfonyl)‐5‐(quinazoline‐5‐yl)‐1,3,4‐oxadiazole, 2‐(((1‐(3,5‐dichlorophenyl)‐1 ‐1,2,3‐triazol‐4‐yl)methyl)sulfonyl)‐5‐(quinazolin‐5‐yl)‐1,3,4‐oxadiazole, 2‐(((1‐(4‐fluorophenyl)‐1 ‐1,2,3‐triazol‐4‐yl)methyl)sulfonyl)‐5‐(quinazoline‐5‐yl)‐1,3,4‐oxadiazole showed strong activity both with IC 50 values ranging from 2.62 ± 0.65 4.21 0.24 µM. exhibited notable kinase 0.34 0.03, 0.36 0.04, 0.43 0.02 µM, respectively. In Silico docking experiments were conducted assess molecular interactions more potent drugs human epidermal growth factor receptor, (PDB: 4HJO) proteins, which included a co‐crystallized ligand (erlotinib). results indicated that six active significantly higher binding energies compared standard medications. SWISS/ADME was used estimate pharmacokinetic profile compounds. Geometric optimization also determine structural characteristics compound ‐1,2,3‐triazol‐4‐yl)methyl)sulfonyl)‐5‐(quinazolin‐5‐yl)‐1,3,4‐oxadiazole. electrostatic potential (MEP) HOMO‐LUMO energy gap determined.

Язык: Английский

Synthesis of Quinazoline‐1,3,4‐Oxadiazole Linked 1,2,3‐Triazole Hybrids as Potent EGFR Targeting Antilung Cancer Agents: In Vitro, In Silico, and DFT Studies DOI

Sampath peddapelli,

Mahadev Bandgar,

Ravikumar Kapavarapu

и другие.

ChemistrySelect, Год журнала: 2025, Номер 10(16)

Опубликована: Апрель 1, 2025

Abstract This research focuses on the design and synthesis of novel quinazoline‐1,3,4‐oxadiazole linked 1,2,3‐triazoles. Subsequently, it investigates their in vitro inhibitory effects EGFR kinases anticancer efficacy against lung cancer cell lines A‐549 H1299. Compared to primary compound, erlotinib, most tested compounds demonstrated superior efficacy. The 2‐(((1‐(3,5‐difluorophenyl)‐1 H ‐1,2,3‐triazol‐4‐yl)methyl)sulfonyl)‐5‐(quinazoline‐5‐yl)‐1,3,4‐oxadiazole, 2‐(((1‐(3,5‐dichlorophenyl)‐1 ‐1,2,3‐triazol‐4‐yl)methyl)sulfonyl)‐5‐(quinazolin‐5‐yl)‐1,3,4‐oxadiazole, 2‐(((1‐(4‐fluorophenyl)‐1 ‐1,2,3‐triazol‐4‐yl)methyl)sulfonyl)‐5‐(quinazoline‐5‐yl)‐1,3,4‐oxadiazole showed strong activity both with IC 50 values ranging from 2.62 ± 0.65 4.21 0.24 µM. exhibited notable kinase 0.34 0.03, 0.36 0.04, 0.43 0.02 µM, respectively. In Silico docking experiments were conducted assess molecular interactions more potent drugs human epidermal growth factor receptor, (PDB: 4HJO) proteins, which included a co‐crystallized ligand (erlotinib). results indicated that six active significantly higher binding energies compared standard medications. SWISS/ADME was used estimate pharmacokinetic profile compounds. Geometric optimization also determine structural characteristics compound ‐1,2,3‐triazol‐4‐yl)methyl)sulfonyl)‐5‐(quinazolin‐5‐yl)‐1,3,4‐oxadiazole. electrostatic potential (MEP) HOMO‐LUMO energy gap determined.

Язык: Английский

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