title: Substituted furans as potent lipoxygenase inhibitors: Synthesis, in vitro and molecular docking studies.
abstract: A number of 2-methyl-4-(2-oxo-2-phenyl-ethyl)-5-phenyl-furan-3-carboxylic acid alkyl ester derivatives (3a-j) were synthesized and evaluated for their in vitro inhibitory activity on soybean lipoxygenase enzyme. Among the screened compounds, 5-(4-bromo-phenyl)-4-[2-(4-bromo-phenyl)-2-oxo-ethyl]-2-methyl-furan-3-carboxylic acid methyl ester (3g) has been found to exhibit potent inhibitory activity with IC5012.8μM using nordihydroguaiaretic acid (NDGA) as standard. Molecular modeling was employed for better understanding of the binding between compounds and soybean lipoxygenase enzyme. The predicted binding energy values correlated well with the observed in vitro data.
authors.affiliation: Laboratory of Catalysis and Chemical Biology, Department of Organic and Medicinal Chemistry, CSIR - Indian Institute of Chemical Biology, 4, Raja S.C. Mullick Road, Kolkata 700 032, India.
authors.forename: Jayaraman
authors.initials: J
authors.lastname: Vinayagam
authors.affiliation: Laboratory of Catalysis and Chemical Biology, Department of Organic and Medicinal Chemistry, CSIR - Indian Institute of Chemical Biology, 4, Raja S.C. Mullick Road, Kolkata 700 032, India.
authors.forename: Rahul L
authors.initials: RL
authors.lastname: Gajbhiye
authors.affiliation: Laboratory of Catalysis and Chemical Biology, Department of Organic and Medicinal Chemistry, CSIR - Indian Institute of Chemical Biology, 4, Raja S.C. Mullick Road, Kolkata 700 032, India.
authors.forename: Likhit
authors.initials: L
authors.lastname: Mandal
authors.affiliation: School of Environmental Studies, Jadavpur University, Kolkata 700 032, India.
authors.forename: Meyyappan
authors.initials: M
authors.lastname: Arumugam
authors.affiliation: Laboratory of Catalysis and Chemical Biology, Department of Organic and Medicinal Chemistry, CSIR - Indian Institute of Chemical Biology, 4, Raja S.C. Mullick Road, Kolkata 700 032, India.
authors.forename: Anushree
authors.initials: A
authors.lastname: Achari
authors.affiliation: Laboratory of Catalysis and Chemical Biology, Department of Organic and Medicinal Chemistry, CSIR - Indian Institute of Chemical Biology, 4, Raja S.C. Mullick Road, Kolkata 700 032, India. Electronic address: jaisankar@iicb.res.in.
authors.forename: Parasuraman
authors.initials: P
authors.lastname: Jaisankar
mesh_terms: D005663:Furans / Q000737:chemistry* / Q000494:pharmacology*; D008084:Lipoxygenase / Q000737:chemistry / Q000378:metabolism*; D016859:Lipoxygenase Inhibitors / Q000737:chemistry* / Q000494:pharmacology*; D062105:Molecular Docking Simulation; D013025:Glycine max / Q000187:drug effects / Q000201:enzymology*
chemical_list: D005663:Furans; D016859:Lipoxygenase Inhibitors; C029060:2-methylfuran; D008084:Lipoxygenase
keywords: Anti-inflammatory; Binding energy; Furan-3-carboxylic acid ester; Molecular docking; Soybean lipoxygenase