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Molecules 2015, 20(2), 1968-1983; doi:10.3390/molecules20021968

Synthesis and Biological Evaluation of Novel 6-Hydroxy-benzo[d][1,3]oxathiol-2-one Schiff Bases as Potential Anticancer Agents

1
Programa de Pós-Graduação em Química, Instituto de Química, Universidade Federal Fluminense, Outeiro de São João Batista s/no, Centro, Niterói 24020-141, RJ, Brazil
2
School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK
3
Fundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos-Farmanguinhos, Rua Sizenando Nabuco 100, Manguinhos, Rio de Janeiro 21041-250, RJ, Brazil
4
Instituto de Ciências Biológicas, Universidade Federal do Pará, Av. Augusto Corrêa 01, Guamá, Belém 66075-110, PA, Brazil
5
Departamento de Química, Instituto de Ciências Exatas, Universidade Federal Fluminense, Rua Desembargador Ellis Hemydio Figueira 783, Aterrado, Volta Redonda 27213-415, RJ, Brazil
6
Department of Chemistry, University of Aberdeen, Old Aberdeen AB 24 3UE, Scotland
7
CHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland
*
Author to whom correspondence should be addressed.
Academic Editor: Jean Jacques Vanden Eynde
Received: 29 September 2014 / Revised: 25 December 2014 / Accepted: 31 December 2014 / Published: 27 January 2015
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Abstract

With the aim of discovering new anticancer agents, we have designed and synthesized novel 6-hydroxy-benzo[d][1,3]oxathiol-2-one Schiff bases. The synthesis started with the selective nitration at 5-position of 6-hydroxybenzo[d][1,3]oxathiol-2-one (1) leading to the nitro derivative 2. The nitro group of 2 was reduced to give the amino intermediate 3. Schiff bases 4ar were obtained from coupling reactions between 3 and various benzaldehydes and heteroaromatic aldehydes. All the new compounds were fully identified and characterized by NMR (1H and 13C) and specifically for 4q by X-ray crystallography. The in vitro cytotoxicity of the compounds was evaluated against cancer cell lines (ACP-03, SKMEL-19 and HCT-116) by using MTT assay. Schiff bases 4b and 4o exhibited promising cytotoxicity against ACP-03 and SKMEL-19, respectively, with IC50 values lower than 5 μM. This class of compounds can be considered as a good starting point for the development of new lead molecules in the fight against cancer. View Full-Text
Keywords: 1,3-benzoxathiol-2-ones; Schiff bases; anticancer; X-ray diffraction; Lipinski’s rule of five 1,3-benzoxathiol-2-ones; Schiff bases; anticancer; X-ray diffraction; Lipinski’s rule of five
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Chazin, E.L.; Sanches, P.S.; Lindgren, E.B.; Vellasco Júnior, W.T.; Pinto, L.C.; Burbano, R.M.R.; Yoneda, J.D.; Leal, K.Z.; Gomes, C.R.B.; Wardell, J.L.; Wardell, S.M.S.V.; Montenegro, R.C.; Vasconcelos, T.R.A. Synthesis and Biological Evaluation of Novel 6-Hydroxy-benzo[d][1,3]oxathiol-2-one Schiff Bases as Potential Anticancer Agents. Molecules 2015, 20, 1968-1983.

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