Synthesis, Genotoxicity and UV-protective Activity of New Benzofuroxans Substituted by Aromatic Amines

Elena      Alexandrovna Chugunova; Marina      Alexandrovna Sazykina; Elmira      Mingaleevna Gibadullina; Alexander      Romanovich Burilov; Ivan      Sergeevich Sazykin; Vladimir      Anatolevich Chistyakov; Rezeda      Eduardovna Timasheva; Dmitry      Borisovich Krivolapov; Regis      Goumont

Abstract

The synthesis of new organic compounds possessing properties, which can be used for biological or pharmaceutical purpose, is very challenging and is a current trend in heterocyclic chemistry. So benzofuroxans are of great interest from a medical and combinatory chemistry point of view, being effective biologically active compounds. They are easily available, easily tuned and functionalized allowing the creation of databases in which a chemist can find proper informations to prepare the structurally appropriate compound with the requested selective effect. In this work, heterocyclic compounds are prepared on the basis of the interaction of 4,6-dichloro-5-nitrobenzofuroxan with aromatic amines and diamines. Their ability to suppress and prevent genotoxic effects of UV-radiation in the wavelength range between 300–400 nm has been studied. It has been shown that these compounds are able to protect bacterial cells from destructive effects of the UV-radiation. Comparing the results obtained for various benzofuroxans to those obtained for the natural antioxidant α - tocopherol (vitamin E) and for the synthetic antioxidant trolox, which are references in this domain, we have shown that some benzofuroxans quantitatively exhibit a similar protective effect, and that compounds prepared from the reaction between 4,6-dichloro-5-nitrobenzofuroxan and ethylenedianiline possess potent protective potential.

Keywords: Antioxidant, Benzofuroxan, Genotoxicity, lux-biosensor, SNAr, UV-radiation, nitro-benzofuroxans, Dinitro, nitro-benzofuroxans, para-aminobenzoic acid