Synthesis and biological evaluation of fluoro-substituted spiro-isoxazolines as potential anti-viral and anti-cancer agents

Prasanta Das; Sarah Boone; Dipanwita Mitra; Lindsay Turner; Ritesh Tandon; Drazen Raucher; Ashton T. Hamme

doi:10.1039/D0RA06148D

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Synthesis and biological evaluation of fluoro-substituted spiro-isoxazolines as potential anti-viral and anti-cancer agents†

Prasanta Das,

*^a Sarah Boone,^b Dipanwita Mitra,

^b Lindsay Turner,^c Ritesh Tandon,

^b Drazen Raucher^c and Ashton T. Hamme, II

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry and Biochemistry, Jackson State University, Jackson, Mississippi 39217, USA
E-mail: prasanta.das@jsums.edu
Tel: +1-601-203-5149

^b Department of Microbiology and Immunology, University of Mississippi Medical Center, Jackson, Mississippi 39216, USA

^c Department of Cellular and Molecular Biology, University of Mississippi Medical Center, Jackson, Mississippi 39216, USA

Abstract

Electrophilic fluorine-mediated dearomative spirocyclization has been developed to synthesize a range of fluoro-substituted spiro-isoxazoline ethers and lactones. The in vitro biological assays of synthesized compounds were probed for anti-viral activity against human cytomegalovirus (HCMV) and cytotoxicity against glioblastomas (GBM6) and triple negative breast cancer (MDA MB 231). Interestingly, compounds 4d and 4n showed significant activity against HCMV (IC₅₀ ∼ 10 μM), while 4l and 5f revealed the highest cytotoxicity with IC₅₀ = 36 to 80 μM. The synthetic efficacy and biological relevance offer an opportunity to further drug-discovery development of fluoro-spiro-isoxazolines as novel anti-viral and anti-cancer agents.

This article is part of the themed collection: Drug design and discovery

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DOI: https://doi.org/10.1039/D0RA06148D
Article type: Paper
Submitted: 14 Jul 2020
Accepted: 06 Aug 2020
First published: 17 Aug 2020
This article is Open Access

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RSC Adv., 2020,10, 30223-30237

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Synthesis and biological evaluation of fluoro-substituted spiro-isoxazolines as potential anti-viral and anti-cancer agents

P. Das, S. Boone, D. Mitra, L. Turner, R. Tandon, D. Raucher and A. T. Hamme, RSC Adv., 2020, 10, 30223 DOI: 10.1039/D0RA06148D

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Synthesis and biological evaluation of fluoro-substituted spiro-isoxazolines as potential anti-viral and anti-cancer agents†

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Synthesis and biological evaluation of fluoro-substituted spiro-isoxazolines as potential anti-viral and anti-cancer agents

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