Solvent controlled synthesis of 2,3-diarylepoxy indenones and α-hydroxy diarylindanones and their evaluation as inhibitors of DNA alkylation repair

Negi, Rollania and Jena, Tapan Kumar and Jyoti, . and Tuti, Nikhil Kumar and Anindya, Roy and Khan, Faiz Ahmed (2022) Solvent controlled synthesis of 2,3-diarylepoxy indenones and α-hydroxy diarylindanones and their evaluation as inhibitors of DNA alkylation repair. Organic & Biomolecular Chemistry, 20 (29). pp. 5820-5835. ISSN 1477-0520

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Abstract

Herein, we report a novel and unexpected metal-free oxygenation of 2,3-diphenyl-1-indenones, under an oxygen atmosphere (air), to either 2,3-epoxy-2,3-diphenyl-1-indenone or 2-hydroxy-2,3-diphenyl-1-indanone, depending on the conditions. Several bioactive epoxy indenones and one-pot α-hydroxy indanones (α-acyloin) were synthesized from 2,3-diaryl dihydroindanone and 2,3-diarylindenone, respectively. A plausible reaction mechanism is also proposed, where oxygenation would take place at the α-position and further proton abstraction from the β-position leads to epoxy indenone derivatives. A one-pot cis-hydroxy indanone protocol is also achieved directly from biaryl indenone via reduction, epimerization, and oxygenation. The synthesized compounds were evaluated for inhibitory activity against the DNA repair protein AlkB. Among the screened (17 tested) compounds, one epoxide derivative was found to be a specific inhibitor of AlkB enzyme function. © 2022 The Royal Society of Chemistry.

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IITH Creators:

IITH Creators	ORCiD
Anindya, Roy	https://orcid.org/0000-0001-8561-907X
Khan, Faiz Ahmed	UNSPECIFIED

Item Type:

Article

Additional Information:

We are grateful for the financial support from the Science and Engineering Research Board (SERB) grant (EMR/2017/003484), Department of Science and Technology, India. We also acknowledge the contribution of late Mr Bonkuru Raghunath in this project.

Uncontrolled Keywords:

Bioactives; Condition; Controlled synthesis; DNA alkylations; Epoxy; Metal free; One pot; Oxygen atmosphere; Reaction mechanism; Synthesised

Subjects:

Others > Biotechnology
Chemistry

Divisions:

Department of Biotechnology
Department of Chemistry

Depositing User:

. LibTrainee 2021

Date Deposited:

17 Oct 2022 06:48

Last Modified:

17 Oct 2022 06:48