BENZOQUINONE MONO OXIMES DERIVATIVES WITH ANTICANCER ACTIVITYAbstract
Objective: The aim of this study was to evaluate the anticancer activity of a series of six structurally related [1, 4]-Benzoquinone monooximes and to investigate structure-activity relationships (SAR) of these compounds. Materials and Method: The mono-oximes obtained by oximination of para-benzoquinones 1-4 had their structures confirmed by ¹H NMR, 13C NMR. The cytotoxic study was assessed by the MTT assay on three tumor cell lines: HL60 (promyelocytic leukemia), NCI-H292 (lung cancer), and MCF-7 (breast adenocarcinoma). Results: Six oximes were synthetized 2 – methyl-[1,4]-benzoquinone oxime tosylate (I), 5-isopropyl-2-mehyl-[1,4]-benzoquinone oxime tosylate (II), 5-isopropyl-5-mehyl-[1,4]-benzoquinone oxime tosylate (III), 5-isopropyl-2-mehyl-[1,4]-benzoquinone oxime (IV), 2,5-dimethyl-[1,4]-benzoquinone oxime tosylate (V), 2-methyl-[1,4]-benzoquinone oxime tosylate (VI). Compounds II to V showed significant activity against all cell lines; while compound I and VI presented low or no activity. Conclusion: These experimental data lead to the conclusion that oximes (II –V) may be used as potential starting structures for the design of novel anticancer agents.
C. M. Feitosa *, S. d. S. Silva, G. G. C. Militão, D. P. d. Sousa, K. Rashed and L. K. F. Lima
Post-graduate Programs in Chemistry and Pharmaceutical Sciences, Federal University of Piaui, Ininga, Teresina, Piauí, Brazil.
24 August 2020
23 September 2020
22 November 2020
31 December 2020