ORIGINAL RESEARCH Synthesis, biopharmaceutical characterization, and antimicrobial study of novel azo dyes of 7-hydroxy-4-methylcoumarin Pravin S. Jogi • Jyotsana Meshram • Javed Sheikh • Taibi Ben Hadda Received: 25 September 2012 / Accepted: 12 December 2012 Ó Springer Science+Business Media New York 2012 Abstract Herein, we report the synthesis and biophar- maceutical characterization of coumarin based azo com- pounds. The novel coumarin based azo compounds were obtained by the coupling of bis-coumarin (2Z,2 0 Z)-2, 2 0 -[ethane-1,2-diylbis(azan-1-yl-1-ylidene)]bis(4-methylch- roman-7-ol) with diazotized aromatic amines. The com- pounds were fully characterized using spectroscopic analytical method and tested for their antibacterial and antifungal activity. A correlation of structure and activities relationship of these compounds with respect to molecular modeling, Lipinski rule of five, drug-likeness, toxicity profiles, and other physico-chemical properties of drugs are described and verified experimentally. Keywords Bis-coumarins  Azo compounds  Antibacterial/antifungal activity  POM (Petra/Osiris/Molinspiration) analyses Introduction Coumarin derivatives have long been recognized to pos- sess multiple biological activities (Hamdi et al., 2008; Kontogiorgis and Hadjipavlou-Litina, 2005; Lee et al., 2006; Matos et al., 2009), especially antioxidant and anti- inflammatory activities; and the coumarin unit can be found in many natural and synthetic drug molecules. Moreover, as an important class of organic heterocyclic dyes, coumarin derivatives exhibit unique photochemical and photo physical properties, which render them useful in a variety of application such as optical brightness, laser dyes, non-linear optical chromophores, solar energy col- lectors, fluorescent labels and probes in biology and med- icine, as well as two-photon absorption (TPA) materials (Fu et al., 2008; Kim et al., 2007, 2008; Li et al., 2007; Melavanki et al., 2008). More importantly, coumarin dyes have also been used as blue, green, and red dopants in organic light-emitting diodes (OLEDs). In well-known family of coumarin derivatives, bimeric coumarins (also called bis-coumarins) occupy an interesting position. These compounds occur naturally in a large number of plants and microorganisms (Murray et al., 1982). The application of coumarin dyes to polyester fabric gave greenish-yellow to orange shades (Yazdanbakhsh et al., 2007). Here, we reported the synthesis of new coumarin deriv- atives containing two coumarin moieties linked together by an ethylenediamine (EDA) molecule. It is achieved when 7-hydroxy-4-methylcoumarin condensed with EDA. Some new azo dyes were also synthesized by coupling Electronic supplementary material The online version of this article (doi:10.1007/s00044-012-0421-3) contains supplementary material, which is available to authorized users. P. S. Jogi Janata Mahavidyalaya, Chandrapur 442401, India e-mail: jogipravin@yahoo.com J. Meshram Department of Chemistry, RTM Nagpur University, Nagpur 440033, India e-mail: drjsmeshram@rediffmail.com J. Sheikh (&) Department of Chemistry, Dhote Bandhu Science College, Gondia 441614, India e-mail: sheikhchemie@gmail.com; javedchemie@gmail.com T. Ben Hadda Laboratoire Chimie Mate´riaux, FSO, Universite´ Mohammed I, 60000 Oujda, Morocco e-mail: tbenhadda@yahoo.fr 123 Med Chem Res DOI 10.1007/s00044-012-0421-3 MEDICINAL CHEMISTRY RESEARCH