2-Amino-4-(nitroalkyl)-4H-chromene-3-carbonitriles as  New Cytotoxic Agents

Zonouzi, Afsaneh; Mirzazadeh, Roghieh; Safavi, Maliheh; Ardestani, Sussan K; Emami, Saeed; Foroumadi, Alireza

doi:10.22037/ijpr.2013.1396

2-Amino-4-(nitroalkyl)-4H-chromene-3-carbonitriles as New Cytotoxic Agents

Document Type : Research article

Authors

¹ School of Chemistry, University College of Science, University of Tehran, P.O. Box 14155-6455, Tehran, Iran

² Institute of Biochemistry and Biophysics, Department of Biochemistry, University of Tehran, Tehran, Iran

³ Department of Medicinal Chemistry and Pharmaceutical Sciences Research Center, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran.

⁴ 1- Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran. 2- Drug Design and Development Research Center, Tehran University of Medical Sciences, Tehran, Iran.

10.22037/ijpr.2013.1396

Abstract

A series of 2-amino-4-(nitroalkyl)-4H-chromene-3-carbonitriles were synthesized by an efficient multicomponent reaction in aqueous media using DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) as a catalyst at room temperature. Mild condition, environment friendly procedure and excellent yields are the main advantages of this procedure. The cytotoxic activity of target compounds were evaluated against three cancer cell lines MDA-MB-231, MCF-7 and T47D in comparison with etoposide as reference drug. Generally, all compounds showed good cell growth inhibitory activity with IC50 values less than 30 μg/mL. Their activities were comparable or more potent than standard drug etoposide. The 6-bromo- derivatives 7e and 7f showed promising cytotoxic activity with IC50 values in the range of 3.46–18.76 μg/mL, being more potent than etoposide against all tested cell lines.

Keywords: 4H-chromenes; Benzopyran; DBU; One-pot synthesis; Cytotoxic activity

Keywords