title: Synthesis and biological evaluation of 5-benzylidenerhodanine-3-acetic acid derivatives as AChE and 15-LOX inhibitors.
abstract: A series of 5-benzylidenerhodanine-3-acetamides bearing morpholino-, 4-arylpiperazinyl-, or 4-benzylpiperidinyl- moieties were synthesized and their inhibitory activities against acetylcholinesterase (AChE) were evaluated. Alteration of amide part and substitution on the benzylidene moiety resulted in change of anti-AChE activity. The most active compound was the 1-benzylpiperidinyl derivative containing 4-(dimethylamino)benzylidene scaffold. Notably, the intermediate compounds, namely 5-arylidene-rhodanine-3-acetic acids (3), showed mild inhibitory activity against 15-lipoxygenase (15-LOX), while the final compound 4 showed no activity against 15-LOX.
authors.affiliation: Tehran University of Medical Sciences, International Campus (TUMS-IC) , Tehran , Iran .
authors.forename: Negah
authors.initials: N
authors.lastname: Shafii
authors.forename: Mehdi
authors.initials: M
authors.lastname: Khoobi
authors.forename: Mohsen
authors.initials: M
authors.lastname: Amini
authors.forename: Amirhossein
authors.initials: A
authors.lastname: Sakhteman
authors.forename: Hamid
authors.initials: H
authors.lastname: Nadri
authors.forename: Alireza
authors.initials: A
authors.lastname: Moradi
authors.forename: Saeed
authors.initials: S
authors.lastname: Emami
authors.forename: Ebrahim
authors.initials: E
authors.lastname: Saeedian Moghadam
authors.forename: Alireza
authors.initials: A
authors.lastname: Foroumadi
authors.forename: Abbas
authors.initials: A
authors.lastname: Shafiee
mesh_terms: D000085:Acetates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000110:Acetylcholinesterase / Q000378:metabolism*; D001093:Arachidonate 15-Lipoxygenase / Q000378:metabolism*; D002800:Cholinesterase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D016859:Lipoxygenase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D062105:Molecular Docking Simulation; D015394:Molecular Structure; D012236:Rhodanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D000085:Acetates; D002800:Cholinesterase Inhibitors; D016859:Lipoxygenase Inhibitors; D012236:Rhodanine; D001093:Arachidonate 15-Lipoxygenase; D000110:Acetylcholinesterase
keywords: 15-lipoxygenase; 2-Thioxothiazolidin-4-one; acetylcholinesterase; docking study; inhibitors; rhodanines