title: Design, synthesis and the biological evaluation of new 1,3-thiazolidine-4-ones based on the 4-amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one scaffold.
abstract: New thiazolidine-4-one derivatives based on the 4-aminophenazone (4-amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one) scaffold have been synthesized as potential anti-inflammatory drugs. The pyrazoline derivatives are known especially for their antipyretic, analgesic and anti-inflammatory effects, but recently there were synthesized new compounds with important antioxidant, antiproliferative, anticancer and antidiabetic activities. The beneficial effects of these compounds are explained by nonselective inhibition of cyclooxygenase izoenzymes, but also by their potential scavenging ability for reactive oxygen and nitrogen species. The structure of the new compounds was proved using spectroscopic methods (FR-IR, 1H-NMR, 13C-NMR, MS). The in vitro antioxidant potential of the synthesized compounds was evaluated according to the ferric reducing antioxidant power, phosphomolydenum reducing antioxidant power, DPPH and ABTS radical scavenging assays. The chemical modulation of 4-aminophenazone (6) through linkage to thiazolidine-propanoic acid derivatives 5a-l led to improved antioxidant potential, all derivatives 7a-l being more active than phenazone. The most active compounds are the derivatives 7e, and 7k, which showed the higher antioxidant effect depending on the antioxidant assay considered.
authors.affiliation: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Medicine and Pharmacy "Grigore T. Popa", 16 University Street, Iasi 700115, Romania. mariasutu@yahoo.com.
authors.forename: Maria
authors.initials: M
authors.lastname: Apotrosoaei
authors.affiliation: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Medicine and Pharmacy "Grigore T. Popa", 16 University Street, Iasi 700115, Romania. ioanageangalau@yahoo.com.
authors.forename: Ioana Mirela
authors.initials: IM
authors.lastname: Vasincu
authors.affiliation: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Medicine and Pharmacy "Grigore T. Popa", 16 University Street, Iasi 700115, Romania. mwolszleger@yahoo.com.
authors.forename: Maria
authors.initials: M
authors.lastname: Dragan
authors.affiliation: Institute of Organic and Analytical Chemistry, University of Orléans, Orléans 45076, Cedex 2, France. frederic.buron@univ-orleans.fr.
authors.forename: Frédéric
authors.initials: F
authors.lastname: Buron
authors.affiliation: Institute of Organic and Analytical Chemistry, University of Orléans, Orléans 45076, Cedex 2, France. sylvain.routier@univ-orleans.fr.
authors.forename: Sylvain
authors.initials: S
authors.lastname: Routier
authors.affiliation: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Medicine and Pharmacy "Grigore T. Popa", 16 University Street, Iasi 700115, Romania. lprofire@mail.umfiasi.ro.
authors.forename: Lenuta
authors.initials: L
authors.lastname: Profire
mesh_terms: D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015195:Drug Design; D004353:Drug Evaluation, Preclinical; D009682:Magnetic Resonance Spectroscopy; D011720:Pyrazoles / Q000737:chemistry*; D053778:Thiazolidines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000975:Antioxidants; D011720:Pyrazoles; D053778:Thiazolidines