<abstract xml:lang="en" xmlns="http://www.w3.org/1999/xhtml">Novel primaquine conjugates with non-steroidal anti-inlammatory drugs (PQ-NSAIDs, <bold>4a-h</bold>) were prepared, fully chemically characterized and screened for radical scavenging and antioxidant activities. The synthetic procedure leading to twin drugs <bold>4a-h</bold> involved two steps: <italic>i</italic>) preparation of NSAID benzotriazolides <bold>3a-h</bold> from the corresponding NSAID (ibuprofen, ketoprofen, fenoprofen, ketoprofen hydroxy and methylene analogues, diclofenac or indomethacin) and benzotriazole carboxylic acid chloride (BtCOCl, <bold>1</bold>), <italic>ii</italic>) reaction of intermediates <bold>3a-h</bold> with PQ. The prepared PQ-NSAIDs exerted moderate activities in the DPPH free radical test and β-carotene-linoleic acid assay. Moreover, ketoprofen derivatives <bold>4d</bold> and <bold>4b</bold> demonstrated a notable Fe2+ chelating ability as well. On the other hand, negligible antiproliferative and antituberculotic effects of conjugates <bold>4a-h</bold> were observed.</abstract>

Novel primaquine conjugates with non-steroidal anti-inlammatory drugs (PQ-NSAIDs, 4a-h) were prepared, fully chemically characterized and screened for radical scavenging and antioxidant activities. The synthetic procedure leading to twin drugs 4a-h involved two steps: i) preparation of NSAID benzotriazolides 3a-h from the corresponding NSAID (ibuprofen, ketoprofen, fenoprofen, ketoprofen hydroxy and methylene analogues, diclofenac or indomethacin) and benzotriazole carboxylic acid chloride (BtCOCl, 1), ii) reaction of intermediates 3a-h with PQ. The prepared PQ-NSAIDs exerted moderate activities in the DPPH free radical test and β-carotene-linoleic acid assay. Moreover, ketoprofen derivatives 4d and 4b demonstrated a notable Fe2+ chelating ability as well. On the other hand, negligible antiproliferative and antituberculotic effects of conjugates 4a-h were observed.

Primaquine-NSAID twin drugs: Synthesis, radical scavenging, antioxidant and Fe2+ chelating activity

Faculty of Pharmacy and Biochemistry, University of Zagreb, Zagreb, Croatia

Institut für Pharmazeutische Wissenschaften, Bereich Pharmakognosie Graz, Austria

Acta Pharmaceutica

Primaquine-NSAID twin drugs: Synthesis, radical scavenging, antioxidant and Fe chelating activity

Novel primaquine conjugates with non-steroidal anti-inlammatory drugs (PQ-NSAIDs, 4a-h) were prepared, fully chemically characterized and screened for radical...

Primaquine-NSAID twin drugs: Synthesis, radical scavenging, antioxidant and Fe²⁺ chelating activity

Publié en ligne: 06 déc. 2010

Pages: 325 - 337

DOI: https://doi.org/10.2478/v10007-010-0024-9

Mots clés
primakin, NSAID, dvojni lijek, konjugat, hvatanje slobodnih radikala, antioksidativno djelovanje, sposobnost keliranja

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