Synthesis and Antioxidant Activity of Novel Quinazolinones Functionalized with Urea/Thiourea/Thiazole Derivatives as 5-Lipoxygenase Inhibitors

被引:28
|
作者
Prashanth, Maralekere K. [1 ]
Revanasiddappa, Hosakere D. [1 ]
机构
[1] Univ Mysore, Dept Chem, Manasagangothri Mysore 570006, Karnataka, India
关键词
Quinazolinone; Thiazole; Thiourea; Antioxidant; 5-LOX; MEDIATED TOTAL-SYNTHESIS; CARBAZOMYCIN-B; ANTIINFLAMMATORY AGENTS; ORGANIC-SYNTHESIS; COMPLEXES; ANTIBACTERIAL; ANALOGS; ACID;
D O I
10.2174/1570180811666131230235157
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
In the present study, a series of novel quinazolinones functionalized with urea/ thiourea/ thiazole derivatives was synthesized and evaluated for their antioxidant and 5-lipoxygenase (5-LOX) inhibition activities. The newly synthesized compounds were characterized using H-1 NMR, C-13 NMR, IR, Mass spectra and elemental analysis. The antioxidant activities of the title compounds were evaluated using DPPH, superoxide, hydroxyl and nitric oxide radical scavenging assay in vitro. It is revealed from the antioxidant screening results that the compounds 3e, 5f and 6c manifested profound antioxidant potential. The synthesized compounds were screened for their 5-LOX inhibitory activity. Overall, 3e, 5f and 6c showed promising antioxidant and 5f showed 5-LOX inhibitory activity and may be used as the lead compounds in the future study.
引用
收藏
页码:712 / 720
页数:9
相关论文
共 50 条
  • [31] Suppression of 5-Lipoxygenase Activity by Anionic Cholesterol Derivatives
    Aleksandrov, D. A.
    Sud'ina, G. F.
    BIOCHEMISTRY MOSCOW-SUPPLEMENT SERIES B-BIOMEDICAL CHEMISTRY, 2007, 1 (02) : 168 - 171
  • [32] Synthesis and Antioxidant Activity of Novel Thiazole and Thiazolidinone Derivatives with Phenolic Fragments
    Koshelev, Vladimir N.
    Primerova, Olga V.
    Vorobyev, Stepan V.
    Stupnikova, Anna S.
    Ivanova, Ludmila V.
    APPLIED SCIENCES-BASEL, 2023, 13 (24):
  • [33] In silico and in vitro antioxidant activity profiles of urea and thiourea derivatives of 5-hydroxytryptophan
    Sudhamani, Hasti
    Prasad, Gandavaram Syam
    Venkataramaiah, Chintha
    Raju, Chamarthi Naga
    Rajendra, Wudayagiri
    JOURNAL OF RECEPTORS AND SIGNAL TRANSDUCTION, 2019, 39 (04) : 373 - 381
  • [34] Synthesis and Biological Evaluation of N-aryl-4-aryl-1,3-Thiazole-2-Amine Derivatives as Direct 5-Lipoxygenase Inhibitors
    Suh, Jeehee
    Yum, Eul Kgun
    Cheon, Hyae Gyeong
    Cho, Young Sik
    CHEMICAL BIOLOGY & DRUG DESIGN, 2012, 80 (01) : 90 - 99
  • [35] OXAZOLE, THIAZOLE, AND IMIDAZOLE DERIVATIVES OF 2,6-DI-TERT-BUTYLPHENOL AS DUAL 5-LIPOXYGENASE AND CYCLOOXYGENASE INHIBITORS
    UNANGST, PC
    CONNOR, DT
    CETENKO, WA
    SORENSON, RJ
    SIRCAR, JC
    WRIGHT, CD
    SCHRIER, DJ
    DYER, RD
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (08) : 1729 - 1734
  • [36] OXAZOLE, THIAZOLE, AND IMIDAZOLE DERIVATIVES OF 2,6-DI-TERT-BUTYLPHENOL AS DUAL 5-LIPOXYGENASE AND CYCLOOXYGENASE INHIBITORS
    UNANGST, PC
    CONNOR, DT
    CETENKO, WA
    SORENSON, RJ
    SIRCAR, JC
    WRIGHT, CD
    SCHRIER, DJ
    DYER, RD
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 206 : 37 - MEDI
  • [37] Synthesis and Structure-Activity Relationship Studies of Novel Dual Inhibitors of Soluble Epoxide Hydrolase and 5-Lipoxygenase
    Meirer, Karin
    Roedl, Carmen B.
    Wisniewska, Joanna M.
    George, Sven
    Haefner, Ann-Kathrin
    Buscato, Estel-la
    Klingler, Franca-Maria
    Hahn, Steffen
    Berressem, Dirk
    Wittmann, Sandra K.
    Steinhilber, Dieter
    Hofmann, Bettina
    Proschak, Ewgenij
    JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (04) : 1777 - 1781
  • [38] Synthesis and biological activity of novel thiourea derivatives as carbonic anhydrase inhibitors
    Korkmaz, Neslihan
    Obaidi, Oday A.
    Senturk, Murat
    Astley, Demet
    Ekinci, Deniz
    Supuran, Claudiu T.
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2015, 30 (01) : 75 - 80
  • [39] 5-HYDROXYANTHRANILIC ACID-DERIVATIVES AS POTENT 5-LIPOXYGENASE INHIBITORS
    OHKUMA, H
    TOMITA, K
    HOSHINO, Y
    SUZUKI, K
    HASEGAWA, M
    SAWADA, Y
    KONISHI, M
    HOOK, DJ
    OKI, T
    JOURNAL OF ANTIBIOTICS, 1993, 46 (05): : 705 - 711
  • [40] Novel and potent inhibitors of 5-lipoxygenase product synthesis based on the structure of pirinixic acid
    Werz, Oliver
    Greiner, Christine
    Koeberle, Andreas
    Hoernig, Christina
    George, Sven
    Popescu, Laura
    Syha, Ivollne
    Schubert-Zsilavecz, Manfred
    Steinhilber, Dieter
    JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (17) : 5449 - 5453