Novel quinolinone-pyrazoline hybrids: synthesis and evaluation of antioxidant and lipoxygenase inhibitory activity

被引：22
作者：
Kostopoulou, Ioanna [1 ]
Diassakou, Antonia [1 ]
Kavetsou, Eleni [1 ]
Kritsi, Eftichia [2 ]
Zoumpoulakis, Panagiotis [2 ]
Pontiki, Eleni [3 ]
Hadjipavlou-Litina, Dimitra [3 ]
Detsi, Anastasia [1 ]
机构：
[1] Natl Tech Univ Athens, Lab Organ Chem, Sch Chem Engn, Zografou Campus, Athens 15780, Greece
[2] Natl Hellen Res Fdn, Inst Chem Biol, 48 Vas Constantinou Ave, Athens 11635, Greece
[3] Aristotle Univ Thessaloniki, Fac Hlth Sci, Sch Pharm, Lab Pharmaceut Chem, Thessaloniki 54124, Greece
来源：
MOLECULAR DIVERSITY | 2021年 / 25卷 / 02期
关键词：
Quinolinones; Chalcones; Pyrazolines; Lipoxygenase; LOX inhibition; Antioxidant activity; BIOLOGICAL EVALUATION; 5-LIPOXYGENASE INHIBITOR; DERIVATIVES; CHALCONES; INFLAMMATION; ANTICANCER; DESIGN; CANCER; 2-PYRAZOLINES; PROGRESSION;
D O I：
10.1007/s11030-020-10045-x
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
The present project deals with the investigation of structure-activity relationship of several quinolinone-chalcone and quinolinone-pyrazoline hybrids, in an effort to discover promising antioxidant and anti-inflammatory agents. In order to accomplish this goal, four bioactive hybrid quinolinone-chalcone compounds (8a-8d) were synthesized via an aldol condensation reaction, which were then chemically modified, forming fifteen new pyrazoline analogues (9a-9o). All the synthesized analogues were in vitro evaluated in terms of their antioxidant and soybean lipoxygenase (LOX) inhibitory activity. Among all the pyrazoline derivatives, compounds 9b and 9m were found to possess the best combined activity, whereas 9b analogue exhibited the most potent LOX inhibitory activity, with IC50 value 10 mu M. The in silico docking results revealed that the synthetic pyrazoline analogue 9b showed high AutoDock Vina score (- 10.3 kcal/mol), while all the tested derivatives presented allosteric interactions with the enzyme.
引用
收藏
页码：723 / 740
页数：18
相关论文
共 79 条
  • [1] Design and synthesis of new 4-pyrazolin-3-yl-1,2,3-triazoles and 1,2,3-triazol-4-yl-pyrazolin-1-ylthiazoles as potential antimicrobial agents
    Abdel-Wahab, Bakr F.
    Abdel-Latif, Ehab
    Mohamed, Hanan A.
    Awad, Ghada E. A.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 52 : 263 - 268
  • [2] Afanasev I. B., 2005, OXIDATION ANTIOXIDAN
  • [3] Almadi M.M., 2019, Eur. J. Chem, V10, P30, DOI [DOI 10.5155/eurjchem.10.1.30-36.1791, 10.5155/eurjchem.10.30-36.1791, DOI 10.5155/EURJCHEM.10.30-36.1791]
  • [4] Crude peroxidase from onion solid waste as a tool for organic synthesis. Part III: synthesis of tetracyclic heterocycles (coumestans and benzofuroquinolinones)
    Angeleska, Simona
    Kefalas, Panagiotis
    Detsi, Anastasia
    [J]. TETRAHEDRON LETTERS, 2013, 54 (19) : 2325 - 2328
  • [5] Azad MB, 2009, ANTIOXID REDOX SIGN, V11, P777, DOI 10.1089/ARS.2008.2270
  • [6] Synthesis and characterization of new 3,5-dinaphthyl substituted 2-pyrazolines and study of their antimicrobial activity
    Azarifar, D
    Shaebanzadeh, M
    [J]. MOLECULES, 2002, 7 (12) : 885 - 895
  • [7] Synthesis, biological evaluation, and docking studies of 3-(substituted)-aryl-5-(9-methyl-3-carbazole)-1H-2-pyrazolines as potent anti-inflammatory and antioxidant agents
    Bandgar, Babasaheb P.
    Adsul, Laxman K.
    Chavan, Hemant V.
    Jalde, Shivkumar S.
    Shringare, Sadanand N.
    Shaikh, Rafique
    Meshram, Rohan J.
    Gacche, Rajesh N.
    Masand, Vijay
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (18) : 5839 - 5844
  • [8] Synthesis and biological evaluation of β-chloro vinyl chalcones as inhibitors of TNF-α and IL-6 with antimicrobial activity
    Bandgar, Babasaheb P.
    Patil, Sachin A.
    Korbad, Balaji L.
    Nile, Shivraj H.
    Khobragade, Chandrahase N.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (06) : 2629 - 2633
  • [9] Synthesis and biological evaluation of simple methoxylated chalcones as anticancer, anti-inflammatory and antioxidant agents
    Bandgar, Babasaheb P.
    Gawande, Shrikant S.
    Bodade, Ragini G.
    Totre, Jalinder V.
    Khobragade, Chandrahas N.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (03) : 1364 - 1370
  • [10] Multifunctional compounds: Smart molecules for multifactorial diseases
    Bansal, Yogita
    Silakari, Om
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 76 : 31 - 42
12345678