SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF 1-(2-METHOXYPHENYL)-(3-(2-PHTHALAMIDO)-PROPYL) PIPERAZINE AND 1-(2-METHOXYPHENYL)-(3-(2-PHTHALAMIDO)-BUTYL) PIPERAZINE
EMMANUEL EIMIOMODEBHEKI ODION*, CYRIL ODIANOSE USIFOH
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Benin, Nigeria.
Afr. J Pharm Res Dev; Volume 13(1): 045-053 (2021)
ABSTRACT
Compounds with piperazine moiety are known to have activity against microbes. The aims of this study were to synthesize, characterize and screen 1-(2-methoxyphenyl)-(3-(2-phthalamido)-propyl) piperazine and 1-(2-methoxyphenyl)-(3-(2-phthalamido)-butyl) piperazine for antibacterial activity. 1-(2-Methoxyphenyl)-(3-(2-phthalamido)-propyl) piperazine was synthesized by refluxing 1-(2-methoxyphenyl) piperazine and anhydrous potassium carbonate in ethane nitrile with N-(3-bromopropyl) phthalimide, while 1-(2-methoxyphenyl)-(3-(2-phthalamido)-butyl) piperazine was obtained by condensing N-(bromobutyl) phthalimide and 1-(2-methoxypheyl) piperazine using acetonitrile as the solvent in anhydrous potassium carbonate in ethane nitrile the for 48 h. Purity of the synthesized compounds was ascertained by determining their melting points, characterization was done using proton nuclear magnetic resonance, carbon-13 nuclear magnetic resonance, Fourier transform infra-red spectroscopy and mass spectrometry. The synthesized compounds were tested for it antibacterial activity using standard method. 1-(2-methoxyphenyl)-(3-(2-phthalamido)-propyl) piperazine was obtained as a yellow crystal, (melting point of 100-102 oC, percentage yield 95 %) by refluxing 1-(2-methoxyphenyl) piperazine and N-(3-bromopropyl) phthalimide. 1-(2-Methoxyphenyl)-(3-(2-phthalamido)-butyl) piperazine was synthesized as yellow solid (melting point of 68-70 oC, percentage yield 90 %) by condensing N-(3-bromobutyl) phthalimide and 1-(2-methoxyphenyl) piperazine. In vivo antibacterial activity showed that 1-(2-methoxyphenyl)-(3-(2-phthalamido)-propyl) piperazine and 1-(2-methoxyphenyl)-(3-(2-phthalamido)-butyl) piperazine have no antibacterial activity. 1-(2-methoxyphenyl)-(3-(2-phthalamido)-propyl) piperazine and 1-(2-methoxyphenyl)-(3-(2-phthalamido)-butyl) piperazine were synthesized, characterized and showed no activity against Escherichia coli, Staphylococci aureus, Pseudomonas aeruginosa, Bacillus subtilis and Klebsiella pneumoniae.
Email of correspondence: emmanuel.odion@uniben.edu
KEYWORDS: Phthalamidoalkyl piperazine; Antibacterial; Condensation.