A facile potassium 18-crown ether catalysed synthesis of 2,6-dicyanoaniline and 3-amino-9,10-dihydrophenanthrene-2,4 dicarbonitrile and their in vitro intercalation study on calf thymus DNA

Abstract

An efficient two-component domino reaction strategy has been developed for the synthesis of 2,6-dicyanoaniline and 3-amino-9,10-dihydrophenanthrene-2,4-dicarbonitrile derivatives in moderate to good yield by the reaction between malononitrile and β-chloro-α,β-unsaturated aldehydes catalyzed by potassium hydroxide-18-crown-6 in methanol. In-vitro intercalation studies of 3-amino-9,10-dihydrophenanthrene-2,4-dicarbonitriles with Calf-Thymus DNA have been carried out which reveal that the moiety interacts with an affinity greater than that of ethidium bromide (EtBr).

Graphical Abstract

Keywords:

• ADA molecule
• DNA intercalation
• potassium-18-crown 6

Acknowledgments

The authors gratefully acknowledge the Department of Chemistry, the University of Calcutta for Crystallographic and NMR studies. The author also thanks Maulana Azad College, Kolkata for use of the departmental facilities.