Synthesis of new indole-2-carboxamide and 3-acetamide derivatives and evaluation their antioxidant properties

被引:18
|
作者
Olgen, Sureyya [1 ]
Bakar, Filiz [2 ]
Aydin, Semra [1 ]
Nebioglu, Dogu [1 ]
Nebioglu, Serpil [2 ]
机构
[1] Ankara Univ, Fac Pharm, Dept Pharmaceut Chem, TR-06100 Ankara, Turkey
[2] Ankara Univ, Fac Pharm, Dept Biochem, TR-06100 Ankara, Turkey
关键词
Indole-2-carboxamide and 3-acetamide; hemeoxygenase; DPPH; antioxidant; HEME OXYGENASE; N-H; INDOLE-DERIVATIVES; SUBSTITUTED INDOLE; INHIBITORS; SERIES; MONOXIDE; PROTEIN; STRESS; SYSTEM;
D O I
10.3109/14756366.2011.631183
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
In recent years, antioxidant compounds play an important role as a health-protecting factor. Antioxidants protect cells against the damaging effects of reactive oxygen species (ROS). An imbalance between antioxidants and ROS results in oxidative stress, which leads to cellular damage and it is linked to many vital diseases. It was shown that heme oxygenase (HO) provides efficient cytoprotection against oxidative stress. In this study, a series of indole-2-carboxamide and 3-acetamide derivatives was tested for in vitro effects on HO activity and 2,2-diphenyl-1-picrylhydrazyl (DPPH) inhibition. Among the synthesized compounds, N-[3-(dimethylamino)propyl]-1H-indole-2-carboxamide 3 was found as the most activator of HO and N-(2-(dimethylamino)ethyl)-2-(1H-indol-3-yl)acetamide 8 was found the most potent inhibitor for DPPH at 10(-4) M concentration.
引用
收藏
页码:58 / 64
页数:7
相关论文
共 50 条
  • [41] SYNTHESIS, ANTIMICROBIAL AND ANTIOXIDANT ACTIVITIES OF 3-SUBSTITUTEDMETHYLENEAMINO-2-BENZOYLBENZOFURANS AND INDOLE DERIVATIVES
    Anand, Saundane R.
    Vijaykumar, Katkar T.
    Kumar, Kiran N. M.
    HETEROCYCLIC LETTERS, 2013, 3 (04): : 443 - 459
  • [42] Synthesis and antioxidant properties of some indole ethylamine derivatives as melatonin analogs
    Ates-Alagoz, Z
    Buyukbingol, Z
    Buyukbingol, E
    PHARMAZIE, 2005, 60 (09): : 643 - 647
  • [43] Indolylarylsulfones as HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors: New Cyclic Substituents at Indole-2-carboxamide
    La Regina, Giuseppe
    Coluccia, Antonio
    Brancale, Andrea
    Piscitelli, Francesco
    Gatti, Valerio
    Maga, Giovanni
    Samuele, Alberta
    Pannecouque, Christophe
    Schols, Dominique
    Balzarini, Jan
    Novellino, Ettore
    Silvestri, Romano
    JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (06) : 1587 - 1598
  • [44] Design, Synthesis and Biological Evaluation of a Novel Series of Indole-3-Carboxamide Derivatives for Cancer Treatment as EGFR Inhibitors
    Zhang, Lan
    Deng, Xin-Shan
    Meng, Guang-Peng
    Zhang, Chao
    Liu, Cong-Chong
    Chen, Gu-Zhou
    Jiang, Xu-Liang
    Zhao, Qing-Chun
    Hu, Chun
    LETTERS IN DRUG DESIGN & DISCOVERY, 2018, 15 (01) : 70 - 83
  • [45] Indole derivatives as multifunctional drugs: Synthesis and evaluation of antioxidant, photoprotective and antiproliferative activity of indole hydrazones
    Demurtas, Monica
    Baldisserotto, Anna
    Lampronti, Ilaria
    Moi, Davide
    Balboni, Gianfranco
    Pacifico, Salvatore
    Vertuani, Silvia
    Manfredini, Stefano
    Onnis, Valentina
    BIOORGANIC CHEMISTRY, 2019, 85 : 568 - 576
  • [46] Synthesis and evaluation of novel N-H and N-substituted indole-2-and 3-carboxamide derivatives as antioxidants agents
    Olgen, Sureyya
    Kilic, Zuhal
    Ada, Ahmet O.
    Coban, Tulay
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2007, 22 (04) : 457 - 462
  • [47] FURO[3,2-B]INDOLE DERIVATIVES .3. STRUCTURE ACTIVITY STUDIES OF 4,6-DISUBSTITUTED N-(3-PIPERIDINOPROPYL)FURO[3,2-B]INDOLE-2-CARBOXAMIDE DERIVATIVES FOR ANALGESIC AND ANTIINFLAMMATORY ACTIVITIES
    KAWASHIMA, Y
    SATO, M
    HATADA, Y
    OKUYAMA, S
    AMANUMA, F
    NAKASHIMA, Y
    SOTA, K
    MORIGUCHI, I
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1986, 34 (08) : 3267 - 3272
  • [48] Synthesis and antioxidant properties of 2-(3-(hydroxyimino)methyl)-1H-indol-1-yl)acetamide derivatives
    Chandravadivelu Gopi
    Magharla Dasaratha Dhanaraju
    Future Journal of Pharmaceutical Sciences, 6
  • [49] STRUCTURE OF 6-CHLORO-4-METHYL-N-(3-PIPERIDINOPROPYL)FURO[3,2-B]INDOLE-2-CARBOXAMIDE
    MIZUNO, H
    KAWASHIMA, Y
    SOTA, K
    KITAMURA, K
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1988, 44 : 202 - 203
  • [50] Synthesis and antioxidant properties of 2-(3-(hydroxyimino)methyl)-1H-indol-1-yl)acetamide derivatives
    Gopi, Chandravadivelu
    Dhanaraju, Magharla Dasaratha
    FUTURE JOURNAL OF PHARMACEUTICAL SCIENCES, 2020, 6 (01)