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
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
  • [1] Synthesis of novel 3-and 5-substituted indole-2-carboxamides
    Bratton, LD
    Roth, BD
    Trivedi, BK
    Unangst, PC
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2000, 37 (05) : 1103 - 1108
  • [2] Synthesis and antitumour evaluation of indole-2-carboxamides against paediatric brain cancer cells
    Alsayed, Shahinda S. R.
    Suri, Amreena
    Bailey, Anders W.
    Lane, Samuel
    Werry, Eryn L.
    Huang, Chiang-Ching
    Yu, Li-Fang
    Kassiou, Michael
    Sredni, Simone Treiger
    Gunosewoyo, Hendra
    RSC MEDICINAL CHEMISTRY, 2021, 12 (11): : 1910 - 1925
  • [3] Synthesis and Antitumour Evaluation of Tricyclic Indole-2-Carboxamides against Paediatric Brain Cancer Cells
    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, 2024, 19 (19)
  • [4] FREE RADICALS OF N-SUBSTITUTED DIHYDROPHENAZINES
    PUSHKARE.ZV
    NOSKOVA, IN
    GRYAZEV, VF
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1970, (10): : 1428 - &
  • [5] Synergistic Interactions of Indole-2-Carboxamides and β-Lactam Antibiotics against Mycobacterium abscessus
    Raynaud, Clement
    Daher, Wassim
    Roquet-Baneres, Francoise
    Johansen, Matt D.
    Stec, Jozef
    Onajole, Oluseye K.
    Ordway, Diane
    Kozikowski, Alan P.
    Kremer, Laurent
    ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2020, 64 (05)
  • [6] CONVENIENT SYNTHESIS OF N-SUBSTITUTED N-CHLOROMETHYL CARBOXAMIDES
    GRONOWITZ, S
    LIDERT, Z
    SYNTHESIS-STUTTGART, 1979, (10): : 810 - 811
  • [7] Investigation of cation radicals of N-substituted phenothiazines
    Tomilin, OB
    Konovalova, EP
    Yuzhalkin, VN
    Ryabkina, LV
    Sanaeva, EP
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1996, (03): : 420 - 426
  • [8] Scavenging of reactive oxygen species by N-substituted indole-2 and 3-carboxamides
    Aboul-Enein, HY
    Kruk, I
    Lichszteld, K
    Michalska, T
    Kladna, A
    Marczynski, S
    Ölgen, S
    LUMINESCENCE, 2004, 19 (01) : 1 - 7
  • [9] Indole-2-Carboxamides Are Active against Mycobacterium abscessus in a Mouse Model of Acute Infection
    Pandya, Amit N.
    Prathipati, Pavan K.
    Hegde, Pooja
    Li, Wei
    Graham, Kyle F.
    Mandal, Subhra
    Drescher, Kristen M.
    Destache, Christopher J.
    Ordway, Diane
    Jackson, Mary
    North, E. Jeffrey
    ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2019, 63 (03)
  • [10] Design, synthesis and evaluation of indole-2-carboxamides with pan anti-mycobacterial activity
    Franz, Nicholas D.
    Belardinelli, Juan Manuel
    Kaminski, Michael A.
    Dunn, Louis C.
    de Moura, Vinicius Calado Nogueira
    Blaha, Michael A.
    Truong, Dan D.
    Li, Wei
    Jackson, Mary
    North, E. Jeffrey
    BIOORGANIC & MEDICINAL CHEMISTRY, 2017, 25 (14) : 3746 - 3755