title: Synthesis, spectral analysis and in vitro microbiological evaluation of 3-(3-alkyl-2,6-diarylpiperin-4-ylidene)-2-thioxoimidazolidin-4-ones as a new class of antibacterial and antifungal agents.
abstract: In the present work, a new series of bis hybrid heterocycle comprising both piperidine and thiohydantoin nuclei together namely 3-(3-alkyl-2,6-diarylpiperin-4-ylidene)-2-thioxoimidazolidin-4-ones 46-60 was synthesized by the treatment of the respective thiosemicarbazones 31-45 with chloroethyl acetate and anhydrous sodium acetate in refluxing ethanol for 4h and were characterized by melting point, elemental analysis, MS, FT-IR, one-dimensional NMR ((1)H, D(2)O exchanged (1)H and (13)C), two dimensional HOMOCOSY and NOESY spectroscopic data. In addition, the title compounds were screened for their antimicrobial activities against a spectrum of clinically isolated microbial organisms. Compounds 47-50, 52-55 and 57-60 with fluoro, chloro, methoxy or methyl functions at the para position of phenyl rings attached to C-2 and C-6 carbons of piperidine moiety along with and without methyl substituent at position C-3 of the piperidine ring exerted potent biological activities against Staphylococcus aureus, beta-Hemolytic streptococcus, Vibrio cholerae, Escherichia coli, Pseudomonas aeruginosa, Aspergillus flavus, Candida albicans, Candida 6 and Candida 51 at a minimum inhibitory concentration.
authors.affiliation: Synthetic Organic Chemistry Laboratory, Department of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamil Nadu, India.
authors.forename: J
authors.initials: J
authors.lastname: Thanusu
authors.forename: V
authors.initials: V
authors.lastname: Kanagarajan
authors.forename: M
authors.initials: M
authors.lastname: Gopalakrishnan
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D048289:Imidazolidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D010880:Piperidines / Q000737:chemistry; D013867:Thiohydantoins / Q000737:chemistry
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D048289:Imidazolidines; D010880:Piperidines; D013867:Thiohydantoins; C032727:piperidine