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

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 syn...

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Bibliographic Details
Published in:Pakistan journal of pharmaceutical sciences 2022-09, Vol.35 (5), p.1391-1398
Main Authors: Kesuma, Dini, Yuniarta, Tegar Achsendo, Putra, Galih Satrio, Sumari, Sumari, Sulistyowaty, Melanny Ika, Anwari, Farida
Format: Article
Language:English
Subjects:
Antimitotic agents
Antineoplastic agents
Chemical properties
Health aspects
Ligases
Pharmaceutical research
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Summary: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 [IC.sub.50] 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. Keywords: Anticancer, benzoxazinone, elucidation, molecular docking, MTT assay.
ISSN:1011-601X
DOI:10.36721/PJPS.2022.35.5.REG.1391-1398.1