title: Synthesis, structure, and bioevaluation of 2,5-bis(arylmethenyl)cyclopentanones.
abstract: Curcumin is an excellent lead compound with a variety of bioactivity. Recent articles reported that curcumin's instability and low bioavailability in vivo are mainly due to its easily decomposable beta-diketone moiety. With the aim of bioactive curcumin analogs with better pharmacokinetic property, we present here 11 bis(arylmethenyl)cyclopentanones similar to curcumin and without beta-diketone moiety by reacting relevant arylaldehydes and cyclopentanones. The analogs were structurally determined by 1HNMR and MS spectra, and the crystal structure of 6 was analyzed by X-ray diffraction. Their antibacterial activities in vitro against seven Gram-positive and Gram-negative bacteria were tested, and their inhibition of TNF-alpha and IL-6 secretion in LPS-induced mouse macrophages was investigated using enzyme-linked immunosorbent assay. It was observed that several derivatives displayed higher activity when compared with curcumin, and most of the analogs exhibited activities against the ampicillin-resistant Gram-negative Enterobacter cloacae.
authors.affiliation: School of Pharmacy, Wenzhou Medical College, Wenzhou, China.
authors.forename: Guang
authors.initials: G
authors.lastname: Liang
authors.forename: Shu-Lin
authors.initials: SL
authors.lastname: Yang
authors.forename: Li-Li
authors.initials: LL
authors.lastname: Shao
authors.forename: Cheng-Guang
authors.initials: CG
authors.lastname: Zhao
authors.forename: Jian
authors.initials: J
authors.lastname: Xiao
authors.forename: Yan-Xia
authors.initials: YX
authors.lastname: Lv
authors.forename: Ju
authors.initials: J
authors.lastname: Yang
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhao
authors.forename: Xiao-Kun
authors.initials: XK
authors.lastname: Li
mesh_terms: D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D002460:Cell Line; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000494:pharmacology*; D004797:Enzyme-Linked Immunosorbent Assay; D008264:Macrophages / Q000187:drug effects; D051379:Mice; D008958:Models, Molecular; D015394:Molecular Structure
chemical_list: D000900:Anti-Bacterial Agents; D000894:Anti-Inflammatory Agents, Non-Steroidal; D003517:Cyclopentanes