title: 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.
abstract: 2-[(2,4-Diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene)hydrazono]-4-phenyl-2,3-dihydrothiazoles (3a-3k) have been synthesized by the cyclization of 2-[(2,4-diaryl-3-azabicyclo[3.3.1]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.
authors.affiliation: Department of Image Science and Engineering, Pukyong National University, Busan 608 737, Republic of Korea.
authors.forename: Rajamanickam
authors.initials: R
authors.lastname: Ramachandran
authors.forename: Paramasivam
authors.initials: P
authors.lastname: Parthiban
authors.forename: Mannangatty
authors.initials: M
authors.lastname: Rani
authors.forename: Sampathkumar
authors.initials: S
authors.lastname: Jayanthi
authors.forename: Senthamaraikannan
authors.initials: S
authors.lastname: Kabilan
authors.forename: Yeon Tae
authors.initials: YT
authors.lastname: Jeong
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001231:Aspergillus flavus / Q000187:drug effects; D053961:Azabicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001412:Bacillus subtilis / Q000187:drug effects; D003455:Cryptococcus neoformans / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D012233:Rhizopus / Q000187:drug effects; D013237:Stereoisomerism
chemical_list: D000890:Anti-Infective Agents; D053961:Azabicyclo Compounds