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.
Highlights
Cancer still remains a threat to huamn health, figuring among the leading causes of death worldwide [1,2]
The Schiff bases 4a–r were prepared from reactions between 3 (1 mmol) and the appropriate benzaldehyde or heteroaromatic aldehyde (1 mmol) in ethanol (10 mL)
The system was kept under stirring at room temperature and the progress of the reactions was monitored by thin-layer chromatography (TLC) using hexane/ethyl acetate (1:1) mixture as eluent
Summary
Cancer still remains a threat to huamn health, figuring among the leading causes of death worldwide [1,2]. Many efforts have been made to develop new strategies for finding effective ways of treating this disease, which include an increase in the understanding of the biological process involved in cancer survival and the search for more selective and potent chemotherapeutic agents [4]. In this context, several heterocyclic systems with five-membered rings fused to a benzene nucleus play an important role on designing of new drugs, since they display an interesting and diversified pharmacological profile. In 2011, our research group has published the first review article highlighting the main aspects of the chemistry and biological properties of 1,3-benzoxathiol-2-ones [5]
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