title: Synthesis and Pharmacochemistry of New Pleiotropic Pyrrolyl Derivatives.
abstract: Within the framework of our attempts to synthesize pleiotropic anti-inflammatory agents, we have synthesized some chalcones and their corresponding 3,4-pyrrolyl derivatives. Chalcones constitute a class of compounds with high biological impact. They are known for a number of biological activities, including anti-inflammatory and free radical scavenging activities. They inhibit several enzymes implicated in the inflammatory process, such as lipoxygenase, cyclooxygenase (COX) and lysozymes. The synthesized pyrroles have been studied for: (1) their in vitro inhibition of lipoxygenase; (2) their in vitro inhibition of COX; (3) their in vitro inhibition of lipid peroxidation; (4) their interaction with the stable, N-centered, free radical, 2,2-diphenyl-1-picrylhydrazyl (DPPH); (5) their inhibition on interleukin-6 (IL-6); (6) their anti-proteolytic activity; and (7) their in vivo anti-inflammatory activity using carrageenan-induced rat paw edema. Their physicochemical properties were determined to explain the biological results. Lipophilicity was experimentally determined. 2i and 2v were found to be promising multifunctional molecules with high antiproteolytic and anti-inflammatory activities in combination with anti-interleukin-6 activity.
authors.affiliation: Department of Pharmaceutical Chemistry, School of Pharmacy, Faculty of Health Sciences, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece. konsmark@hotmail.com.
authors.forename: Markella
authors.initials: M
authors.lastname: Konstantinidou
authors.affiliation: Department of Pharmaceutical Chemistry, School of Pharmacy, Faculty of Health Sciences, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece. germanialisa@gmail.com.
authors.forename: Alice
authors.initials: A
authors.lastname: Gkermani
authors.affiliation: Department of Pharmaceutical Chemistry, School of Pharmacy, Faculty of Health Sciences, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece. hadjipav@pharm.auth.gr.
authors.forename: Dimitra
authors.initials: D
authors.lastname: Hadjipavlou-Litina
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use*; D000975:Antioxidants / Q000378:metabolism; D001713:Biphenyl Compounds / Q000737:chemistry; D002351:Carrageenan / Q000633:toxicity; D047188:Chalcones / Q000737:chemistry; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy*; D015227:Lipid Peroxidation / Q000187:drug effects; D008084:Lipoxygenase / Q000378:metabolism; D010851:Picrates / Q000737:chemistry; D011451:Prostaglandin-Endoperoxide Synthases / Q000378:metabolism; D011758:Pyrroles / Q000737:chemistry*; D051381:Rats
chemical_list: D000893:Anti-Inflammatory Agents; D000975:Antioxidants; D001713:Biphenyl Compounds; D047188:Chalcones; D010851:Picrates; D011758:Pyrroles; D002351:Carrageenan; C004931:1,1-diphenyl-2-picrylhydrazyl; D008084:Lipoxygenase; D011451:Prostaglandin-Endoperoxide Synthases
keywords: anti-cyclooxygenase; anti-inflammatories; anti-lipoxygenase; antioxidant; chalcones; pleiotropic; pyrroles