title: Synthesis and biological evaluation of novel 6-hydroxy-benzo[d][1,3]oxathiol-2-one Schiff bases as potential anticancer agents.
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 4a-r 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.
authors: 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. elizachazin@gmail.com.
authors: Eliza de Lucas
authors: Ede L
authors: Chazin
authors: 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. paolasanches@id.uff.br.
authors: Paola de Souza
authors: Pde S
authors: Sanches
authors: 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. ericblmail@gmail.com.
authors: Eric Brazil
authors: EB
authors: Lindgren
authors: 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. walcimar@gmail.com.
authors: Walcimar Trindade
authors: WT
authors: Vellasco Júnior
authors: Instituto de Ciências Biológicas, Universidade Federal do Pará, Av. Augusto Corrêa 01, Guamá, Belém 66075-110, PA, Brazil. lainecelestino@hotmail.com.
authors: Laine Celestino
authors: LC
authors: Pinto
authors: Instituto de Ciências Biológicas, Universidade Federal do Pará, Av. Augusto Corrêa 01, Guamá, Belém 66075-110, PA, Brazil. rommel@ufpa.br.
authors: Rommel Mario Rodríguez
authors: RM
authors: Burbano
authors: Departamento de Química, Instituto de Ciências Exatas, Universidade Federal Fluminense, Rua Desembargador Ellis Hemydio Figueira 783, Aterrado, Volta Redonda 27213-415, RJ, Brazil. jullianeyoneda@yahoo.com.br.
authors: Julliane Diniz
authors: JD
authors: Yoneda
authors: 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. kzl@vm.uff.br.
authors: Kátia Zaccur
authors: KZ
authors: Leal
authors: Fundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos-Farmanguinhos, Rua Sizenando Nabuco 100, Manguinhos, Rio de Janeiro 21041-250, RJ, Brazil. claudiabrandao@far.fiocruz.br.
authors: Claudia Regina Brandão
authors: CR
authors: Gomes
authors: Fundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos-Farmanguinhos, Rua Sizenando Nabuco 100, Manguinhos, Rio de Janeiro 21041-250, RJ, Brazil. j.wardell@abdn.ac.uk.
authors: James Lewis
authors: JL
authors: Wardell
authors: CHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland. solangewardell@yahoo.co.uk.
authors: Solange Maria Silva Veloso
authors: SM
authors: Wardell
authors: Instituto de Ciências Biológicas, Universidade Federal do Pará, Av. Augusto Corrêa 01, Guamá, Belém 66075-110, PA, Brazil. rcm.montenegro@gmail.com.
authors: Raquel Carvalho
authors: RC
authors: Montenegro
authors: 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. gqothatyana@vm.uff.br.
authors: Thatyana Rocha Alves
authors: TR
authors: Vasconcelos
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D007783:Lactones / Q000138:chemical synthesis* / Q000494:pharmacology; D051379:Mice; D041681:NIH 3T3 Cells; D012545:Schiff Bases / Q000138:chemical synthesis / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D007783:Lactones; D012545:Schiff Bases
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