Synthesis of N-substituted indole-2-carboxamides and investigation of their biochemical responses against free radicals

被引：7
|
作者：
Bozkaya, Pinar
Olgen, Sureyya [1 ]
Coban, Tulay
Nebioglu, Dogu
机构：
[1] Ankara Univ, Fac Pharm, Dept Pharmaceut Chem, TR-06100 Ankara, Turkey
[2] Ankara Univ, Fac Pharm, Dept Pharmaceut Toxicol, Ankara, Turkey
来源：
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY | 2007年 / 22卷 / 03期
关键词：
indole-2-carboxamides; reactive oxygen species; superoxide dismutase; lipid peroxidation; inhibition; synthesis;
D O I：
10.1080/14756360601114742
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 antioxidant role of novel N-substituted indole-2-carboxamides (I2CDs) was investigated for their inhibitory effects on superoxide anion (O-2(-)) and lipid peroxidation (LP). Among the synthesized 12CDs, 3, 4, 6, 8 and 9 significantly inhibited O-2(-) with an inhibition range at 70-98%. Examination of substituent effects on activity showed that both the ortho- and parapositions of the benzamide residue needs to be dichlorinated in order to get a maximum inhibitory effect on superoxide anion. In general, halogenated derivatives were found more active then the non-halogenated ones. However, none of the 12CDs had a significant inhibitory effects on the level of lipid peroxidation; only compounds 7 and 10 moderately decreased LP levels by over 50% at 10(-3) M concentrations.
引用
收藏
页码：319 / 325
页数：7
相关论文
共 50 条
  • [21] Indole-2-carboxamides as New Anti-Mycobacterial Agents: Design, Synthesis, Biological Evaluation and Molecular Modeling against mmpL3
    Bhakhar, Kaushikkumar A.
    Vaghela, Punit V.
    Varakala, Saiprasad D.
    Chudasma, Shrdhhaba J.
    Gajjar, Normi D.
    Nagar, Prinsa R.
    Sriram, Dharmarajan
    Dhameliya, Tejas M.
    CHEMISTRYSELECT, 2022, 7 (26):
  • [22] Design, synthesis, and biological evaluation of indole-2-carboxamides as SARS CoV-2 main protease inhibitors
    Gomaa, Hesham A. M.
    Shaker, Mohamed E.
    Alzarea, Sami I.
    Alsahli, Tariq G.
    Hendawy, Omnia
    Mohammed, Yasser Khamis
    Younes, M. Khaled
    Rahman, Fatema El-Zahraa S. Abdel
    Mohamed, Fatma A. M.
    Raoof, Gehan Fawzy Abdel
    Mahmoud, Mohamed A.
    Gouda, Ahmed M.
    Bakr, Adel G.
    Youssif, Bahaa G. M.
    TETRAHEDRON, 2023, 146
  • [23] Chirally n-substituted indole-2-carbaldehydes. Preparation and use in asymmetric synthesis
    Golantsov N.E.
    Karchava A.V.
    Starikova Z.A.
    Dolgushin F.M.
    Yurovskaya M.A.
    Chemistry of Heterocyclic Compounds, 2005, 41 (10) : 1290 - 1299
  • [24] Chiral N-substituted indole-2-carbaldehydes: preparation and use in asymmetric synthesis
    Golantsev, NE
    Karchava, AV
    Starikova, ZA
    Dolgushin, FM
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2005, (10): : 1540 - 1550
  • [25] Synthesis and Antitumour Evaluation of Tricyclic Indole-2-Carboxamides against Paediatric Brain Cancer Cells (Vol 19, e202400098, 2024)
    Hamilton, Alexander John
    Lane, Samuel
    Werry, Eryn L.
    Suri, Amreena
    Bailey, Anders W.
    Merce, Clementine
    Kadolsky, Ulrich
    Payne, Alan D.
    Kassiou, Michael
    Sredni, Simone Treiger
    Saxena, Alka
    Gunosewoyo, Hendra
    CHEMMEDCHEM, 2025, 20 (05)
  • [26] Synthesis of N-substituted indole derivatives as potential antimicrobial and antileishmanial agents
    Tiwari, Shweta
    Kirar, Seema
    Banerjee, Uttam Chand
    Neerupudi, Kishore Babu
    Singh, Sushma
    Wani, Aabid Abdullah
    Bharatam, Prasad, V
    Singh, Inder Pal
    BIOORGANIC CHEMISTRY, 2020, 99
  • [27] Synthesis and Evaluation of Antimicrobial Activities of Novel N-Substituted Indole Derivatives
    MahamadAlli Shaikh, Tanveer
    Debebe, Habtamu
    JOURNAL OF CHEMISTRY, 2020, 2020
  • [28] A convenient synthesis of indoloquinolinones via 3-arylation of indole-2-carboxamides and PIDA-mediated C-N bond formation
    Li, Yulin
    Zhang-Negrerie, Daisy
    Du, Yunfei
    Zhao, Kang
    TETRAHEDRON, 2015, 71 (19) : 2927 - 2935
  • [29] Novel indole-2-carboxamides are highly potent against drug-sensitive and drug-resistant strains of Mycobacterium tuberculosis
    Stec, Jozef
    Onajole, Oluseye
    Lun, Shichun
    Bishai, William
    Kozikowski, Alan
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [30] Synthesis and antioxidant properties of novel N-substituted indole-2-carboxamide and indole-3-acetamide derivatives
    Ölgen, S
    Çoban, T
    ARCHIV DER PHARMAZIE, 2002, 335 (07) : 331 - 338
12345