title: Synthesis and biological evaluation of new 1,3-thiazolidine-4-one derivatives of 2-(4-isobutylphenyl)propionic acid.
abstract: New thiazolidine-4-one derivatives of 2-(4-isobutylphenyl)propionic acid (ibuprofen) have been synthesized as potential anti-inflammatory drugs. The structure of the new compounds was proved using spectral methods (FR-IR, 1H-NMR, 13C-NMR, MS). The in vitro antioxidant potential of the synthesized compounds was evaluated according to the total antioxidant activity, the DPPH and ABTS radical scavenging assays. Reactive oxygen species (ROS) and free radicals are considered to be involved in many pathological events like diabetes mellitus, neurodegenerative diseases, cancer, infections and more recently, in inflammation. It is known that overproduction of free radicals may initiate and amplify the inflammatory process via upregulation of genes involved in the production of proinflammatory cytokines and adhesion molecules. The chemical modulation of acyl hydrazones of ibuprofen 3a-l through cyclization to the corresponding thiazolidine-4-ones 4a-n led to increased antioxidant potential, as all thiazolidine-4-ones were more active than their parent acyl hydrazones and also ibuprofen. The most active compounds are the thiazolidine-4-ones 4e, m, which showed the highest DPPH radical scavenging ability, their activity being comparable with vitamin E.
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. 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. teutz_panzariu@yahoo.com.
authors.forename: Andreea-Teodora
authors.initials: AT
authors.lastname: Panzariu
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 / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D011422:Propionates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D000975:Antioxidants; D011422:Propionates