Selective and Efficient Synthesis of 1,5-benzodiazepin-2-one and Amino Chromenes as Biologically Versatile Scaffolds

Abstract

A convenient methodology has been disclosed for the synthesis of 1,5-benzodiazepin-2-one and amino chromene-2-one analogues. The synthesized compounds act as biologically potent compared to 4-hydroxycoumarins. The reaction was carried out using 4-hydroxy coumarin and aniline derivatives containing both electron donating and electron withdrawing groups in toluene under reflux at 120°C. A library of compounds has been synthesized using different derivatives of aniline. The product formation has been achieved at stipulated time of 6 hours. The required compounds were obtained using column chromatographic technique and were characterized by 1HNMR, 13C-NMR and mass spectrometry. The products were obtained in high yield with good anticancer activity and significant antibacterial effects. Out of the synthesised derivatives, compound-2a, 2b, 4b, 4e, 4g, 4k displayed selective and potent cytotoxic effects against different cell lines as compared to that of parent compound. Among all the compounds, 4g and 4f were found to be highly active in inhibiting bacterial growth to the significant extent. Simple reaction procedure, better product yield and high biological activity are some outstanding features of the disclosed protocol.