Synthesis of Coumarins Coupled with Benzamides as Potent Antimicrobial Agents
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Pharmaceutical Chemistry Journal, Vol. 54, No. 6, September, 2020 (Russian Original Vol. 54, No. 6, June, 2020)
SYNTHESIS OF COUMARINS COUPLED WITH BENZAMIDES AS POTENT ANTIMICROBIAL AGENTS Muthipeedika Nibin Joy,1,2,* Vasiliy A. Bakulev,3 Yadav D. Bodke,2,4 and Sandeep Telkar5 Original article submitted March 3, 2020. A series of new coumarin derivatives coupled with benzamides have been synthesized and screened for their antimicrobial properties. Some compounds displayed promising antibacterial activity (MIC ranging within 5 – 150 mg/mL) and moderate antifungal activity as compared to the respective standards. Compounds 6p, 6l and 6m displayed promising antibacterial activity comparable with the standard drug ciprofloxacin, and compound 6m exhibited better antifungal activity in comparison to other synthesized compounds. In silico docking studies of the active compounds were carried out against the gyrase enzyme, and it was concluded that compound 6p exhibited significant hydrogen bonding and hydrophobic interactions which could be the plausible reason for its superior activity as compared to the other synthesized compounds. Keywords: coumarin; benzamide; antibacterial; antifungal.
green plants either in free or combined state and display a large spectrum of biological potencies [4]. Natural coumarins and their derivatives are of great interest due to their extensive pharmacological activities and this has intrigued medicinal chemists for their synthesis in the laboratory and for screening them as therapeutic agents. Coumarins are widely reported to be active as antibacterial [5], antiinflammatory [6] and antiviral agents [7]. Various therapeutic applications of coumarin derivatives include photo- and chemotherapy, anti-tumor therapy and anti-HIV therapy [8]. The coumarin moiety is present in the chemical structure of various pharmaceutical drugs like warfarin, acenocoumarol, carbochromen, etc., and in antibiotics such as novobiocin, clorobiocin and coumermycin A1 [9, 10]. In view of these remarkable biological properties, the investigation of novel natural and synthetic coumarin molecules has attracted chemists for decades in the field of drug discovery and medicinal chemistry. In the design and development of new drugs, the roles of amides and thioamides as linkers are well documented in literature [11]. Coumarins attached to amides, for instance, the O-acetamide substituted 4-hydroxy and 7-hydroxy coumarins, are reported to possess anti-acetylcholinesterase activity that is considered to be a promising approach for the treatment of Alzheimer’s disease [12, 13]. Moreover, coumarin-3-carboxamide derivatives are reported to possess significant antibacterial and anticancer activity [14, 15]. Novobiocin and clorobiocin are the two commer-
1. INTRODUCTION Microbial infections are a major growing concern in contemporary medicine, yet only a few antimicrobial agents are used in clinical practice. Organisms like bacteria, fungi and viruses are identified to cause severe health hazards in humans throughout the world
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