In-silico, synthesis, structure elucidation and anticancer activity study of 2-(3,4-dichlorophenyl)-4H-benzo[d][1,3]oxazin-4-one

Kesuma, Dini and Yuniarta, Tegar Achsendo and Putra, Galih Satrio and Sumari, Sumari and Sulistyowaty, Melanny Ika and Anwari, Farida (2022) In-silico, synthesis, structure elucidation and anticancer activity study of 2-(3,4-dichlorophenyl)-4H-benzo[d][1,3]oxazin-4-one. Pakistan Journal of Pharmaceutical Sciences, 35 (5). pp. 1391-1398.

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The research aims to synthesize 2-(3,4-dichlorophenyl)-4H-benzo[d][1,3]oxazin-4-one and evaluate its anticancer activity against MCF-7. This compound was selected based on in-silico study conducted against several dihalophenylbenzoxazinone analogues using molecular docking towards Methionyl-tRNA synthetase. Synthesis of target compound was carried out using anthranilic acid and 3,4-dichlorobenzoyl chloride. The resulting compound was characterized using various spectroscopic analysis: 1D and 2D NMR, infrared and MS. In-silico studies was performed by MVD. Several designed compounds were docked into the active site on Methionyl-tRNA Synthetase (1PG2). Anticancer activity was evaluated by MTT Assay against MCF-7. 2-(3,4-dichlorophenyl)-4H-benzo[d][1,3]oxazin-4-one has been successfully synthesized with decent amount of yield 88 %. Its spectroscopic analysis 1D and 2D NMR, MS, FTIR has proven the chemical structure of compound. In-silico studies toward the enzyme showed docking score of - 76.04 Kcal/mol, higher than its native ligand (-93.50 Kcal/mol). Meanwhile, MTT assay result against MCF-7 showed IC50 value of 68.59ppm. Based on preliminary in-silico studies inhibited Methionyl-tRNA Synthetase, 2-(3,4- dichlorophenyl)-4H-benzo[d][1,3]oxazin-4-one was synthesized and tested in-vitro against MCF-7. Albeit the compound does not possess better docking score than native ligand, it is still argued that benzoxazine ring can be considered as a potential anticancer agent, as showed by MTT assay result which indicated moderate cytotoxicity.

Item Type: Article
Uncontrolled Keywords: Anticancer, benzoxazinone, elucidation, molecular docking, MTT assay
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Pharmacy > Department of Pharmacy
Date Deposited: 16 Sep 2022 08:24
Last Modified: 01 Sep 2023 02:41

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