title: Synthesis, crystal and antibacterial studies of diversely functionalized tetrahydropyridin-4-ol.
abstract: In an effort to expand the spectrum of antibacterial activity associated with piperidin-4-one derivatives, we have synthesized two series of 3-carboxyethyl-2,6-diphenyl-4-hydroxy-Delta(3)-tetrahydropyridine derivatives bearing diversified heterocyclic and aromatic systems at the nitrogen atom through acetyl (6-18) and 2-propanoyl (9-31) linkers. Unlike acetyl derivatives, NMR spectral pattern of the propanoyl counterparts revealed the existence of pair of rotational isomers (syn and anti) in solution at room temperature due to the hindered rotation about N-CO bond. X-ray crystal studies of 9 and 24 clearly pointed out that all the compounds existed in only one form particularly, in stable syn form in solid state. Each of the compounds was screened for their in vitro antibacterial activity against nine human pathogenic gram-positive strains including multiple drug resistant organisms and seven problematic gram-negative strains. Among the various heterocycles examined here, imidazole substituted derivatives 12 and 25 exhibited antibacterial activity approaching that of Linezolid and Trovafloxacin drugs particularly against multiple resistant Enterococcus faecium-VanA phenotype strains.
authors.affiliation: Division of Image Science and Information Engineering, Pukyong National University, Busan 608-739, Republic of Korea.
authors.forename: Gopalakrishnan
authors.initials: G
authors.lastname: Aridoss
authors.forename: Shanmugasundaram
authors.initials: S
authors.lastname: Amirthaganesan
authors.forename: Yeon Tae
authors.initials: YT
authors.lastname: Jeong
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects*; D001424:Bacterial Infections / Q000188:drug therapy; D018360:Crystallography, X-Ray; D006801:Humans; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000900:Anti-Bacterial Agents; D011725:Pyridines