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Synthesis, stereochemistry and in vitro antimicrobial evaluation of novel 2-[(2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene)hydrazono]-4-phenyl-2,3-dihydrothiazoles
Authors:Ramachandran Rajamanickam  Parthiban Paramasivam  Rani Mannangatty  Jayanthi Sampathkumar  Kabilan Senthamaraikannan  Jeong Yeon Tae
Institution:Department of Image Science and Engineering, Pukyong National University, Busan 608 737, Republic of Korea.
Abstract:2-(2,4-Diaryl-3-azabicyclo3.3.1]nonan-9-ylidene)hydrazono]-4-phenyl-2,3-dihydrothiazoles (3a-3k) have been synthesized by the cyclization of 2-(2,4-diaryl-3-azabicyclo3.3.1]nonan-9-one thiosemicarbazones with phenacyl bromide and characterized by analytical (melting point and elemental analysis) and spectral (IR, (1)H NMR, (13)C NMR, D(2)O exchange, NOESY and mass) techniques. The novel Hantzsch products (3a-3k) were screened for their in vitro antibacterial and antifungal activities against some selected microorganisms. Structure activity relationship (SAR) for the reported compounds was studied by comparing their MIC values with standard drugs (Streptomycin and Amphotericin B). The results show that 3e against Escherichia coli and Cryptococcus neoformans3i against Bacillus Subtilis, 3b against Aspergillus flavus, and 3k against Rhizopus sp. were found to show significant growth inhibition.
Keywords:Hantzsch thiazoles  Azabicyclo[3  3  1]nonan-9-ones  Antibacterial activity  Antifungal activity  Stereochemistry
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