J. Iran. Chem. Soc., Vol. 6, No. 2 June 2009, pp.325~333.

Current location: JICS Archive > Vol. 6 > No. 2 > Articles : 12

Synthesis and Antibacterial Activity of N-[2-(2-naphthyl)ethyl]piperazinyl Quinolones

A. Shafieea,b,*, S. Emamic, S. Ghodsid, S. Najjaria, M. Sorkhia,  N. Samadie, M.A. Faramarzie and A. Foroumadia,b

aDepartment of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran 14174, Iran
Drug Design & Development Research Center, Tehran University of Medical Sciences, Tehran 14174, Iran
Department of Medicinal Chemistry and Pharmaceutical Sciences Research Center, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran
Department of Chemistry, Faculty of Sciences, Islamic Azad University, Karaj-Branch, Karaj, Iran
Department of Pharmaceutical Biotechnology, Tehran University of Medical Sciences, Tehran 14174, Iran

A series of N-[2-(2-naphthyl)ethyl]piperazinyl quinolones containing a carbonyl related functional groups (oxo- or oxyimino-) on the ethyl spacer was synthesized and evaluated for antibacterial activity. The synthesis of N-[2-(2-naphthyl)ethyl]piperazinyl quinolones was achieved through the versatile and efficient synthetic route that involved reaction of piperazinyl quinolones with appropriate α-bromoketone or α-bromooxime derivatives. The structures of new compounds were confirmed by elemental analysis, IR and NMR spectra. Antibacterial data indicated that some of the new N-[2-(2-naphthyl)ethyl]piperazinyl quinolones showed good antibacterial activity and modification of the position 8 and N-1 substituent on quinolone ring, and ethyl spacer functionality produced significant changes in activity against Gram-positive and Gram-negative bacteria.

Keywords: Fluoroquinolones, Piperazinyl quinolones, Antibacterial activity, Structure-activity relationships

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