An efficient synthesis of 3′-indolyl substituted pyrido[1,2-a]benzimidazoles as potential antimicrobial and antioxidant agents

被引:17
|
作者
Kathrotiya, Harshad G. [1 ]
Patel, Manish P. [1 ]
机构
[1] Sardar Patel Univ, Dept Chem, Vallabh Vidyanagar 388120, Gujarat, India
关键词
Indole; pyrido[1,2-a]benzimidazoles; multicomponent reaction; antimicrobial activity; FRAP assay; CONDENSED RING-SYSTEMS; DERIVATIVES BEARING; INDOLE-DERIVATIVES; ANTIVIRAL ACTIVITY; RECEPTOR;
D O I
10.1007/s12039-013-0468-9
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new class of indole-based pyrido[1,2-a]benzimidazole derivatives 4a-r have been synthesized by one-pot cyclocondensation reaction of 2-phenyl-1H-indole-3-carboxaldehyde 1a-i, malononitrile 2 and 2-cyanomethylbenzimidazole 3a-b in the presence of catalytic amount of NaOH. In vitro antimicrobial activity of the synthesized compounds were investigated against a representative panel of pathogenic strains specifically three Gram-positive bacteria (Streptococcus pneumoniae, Clostridium tetani, Bacillus subtilis), three Gram-negative bacteria (Salmonella typhi, Vibrio cholerae, Escherichia coli) and two fungi (Aspergillus fumigatus, Candida albicans) using broth microdilution MIC (minimum inhibitory concentration) method. In vitro antioxidant activity was evaluated by ferric-reducing antioxidant power (FRAP) assay method. Compounds 4c, 4e, 4l and 4q have been found to be most efficient antimicrobial members while compounds 4h and 4p possess better ferric reducing antioxidant power.
引用
收藏
页码:993 / 1001
页数:9
相关论文
共 50 条
  • [21] Synthesis and Antimicrobial, Antioxidant, ADME-T, and Molecular Docking Studies of Imidazo[1,2-a]pyridine Derivatives
    Koudad, M.
    Dadou, S.
    Abrigach, F.
    Aatiaoui, A. El
    Azzouzi, M.
    Oussaid, A.
    Benchat, N.
    Allali, M.
    Karrouchi, K.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 59 (07) : 1237 - 1247
  • [22] 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
  • [23] Synthesis and Antimicrobial, Antioxidant, ADME-T, and Molecular Docking Studies of Imidazo[1,2-a]pyridine Derivatives
    M. Koudad
    S. Dadou
    F. Abrigach
    A. El Aatiaoui
    M. Azzouzi
    A. Oussaid
    N. Benchat
    M. Allali
    K. Karrouchi
    Russian Journal of Organic Chemistry, 2023, 59 : 1237 - 1247
  • [24] Microwave-assisted multicomponent reaction: An efficient synthesis of indolyl substituted and spiroxindole pyrido[2,3-d]pyrimidine derivatives
    Wang, Jing
    Zhu, Shuang
    Liu, Yanni
    Zhu, Xiaotong
    Shi, Kexin
    Li, Xiang
    Zhu, Songlei
    SYNTHETIC COMMUNICATIONS, 2022, 52 (01) : 85 - 95
  • [25] Synthesis of Pyridyl Benzimidazoles Encompassing 4-Thiazolidinone Derivatives as Potential Antimicrobial Agents
    Desai, N. C.
    Pandya, D. D.
    Kotadiya, G. M.
    Desai, Priyanka
    LETTERS IN DRUG DESIGN & DISCOVERY, 2013, 10 (10) : 942 - 950
  • [26] SC2WT Pyrimido[1,2-a]benzimidazoles: synthesis and perspective of their pharmacological use
    Fedotov, Victor V.
    Rusinov, Vladimir L.
    Ulomsky, Evgeny N.
    Mukhin, Evgeny M.
    Gorbunov, Evgeny B.
    Chupakhin, Oleg N.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2021, 57 (04) : 383 - 409
  • [27] Microwave assisted synthesis of 2,4-disubstituted pyrimido-[1,2-a]-benzimidazoles
    Deshmukh, M. B.
    Suryavanshi, A. W.
    Deshmukh, S. A.
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2008, 85 (03) : 330 - 332
  • [28] SYNTHESIS OF HALOGENATED 4H-PYRIDO[1,2-a]PYRIMIDIN-4-ONES
    Molnar, Annamaria
    Faigl, Ferenc
    Podanyi, Benjamin
    Finta, Zoltan
    Balazs, Laszlo
    Hermecz, Istvan
    HETEROCYCLES, 2009, 78 (10) : 2477 - 2488
  • [29] An efficient synthesis of some new 3-bipyridinyl substituted coumarins as potent antimicrobial agents
    Lad, Hemali B.
    Giri, Rakesh R.
    Brahmbhatt, D. I.
    CHINESE CHEMICAL LETTERS, 2013, 24 (03) : 227 - 229
  • [30] An efficient synthesis of some new 3-bipyridinyl substituted coumarins as potent antimicrobial agents
    Hemali B.Lad
    Rakesh R.Giri
    D.I.Brahmbhatt
    Chinese Chemical Letters, 2013, 24 (03) : 227 - 229