American Journal of Heterocyclic Chemistry

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Aqueous Synthesis and Biological Studies of Indole Derivatives

Received: 26 October 2016    Accepted: 12 November 2016    Published: 27 December 2016
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Abstract

One pot with expedient approach to the synthesis of 2,3-disubstituted indole derivatives using indium (III) trichloride through Fisher indole method has been developed, in aqueous media. The synthesized compounds were screened for their anti analgesic and antibacterial activity. All the six indole derivatives exhibited significant antibacterial activity against Pseudomonas aeruginosa when compared to standard drug Ciprofloxacin. Based on the results of antibacterial activity, the molecular docking of all six indole derivatives were performed against Pseudomonas elastase a matrix metalloproteinase from Pseudomonas aeruginosa were presumed as an infectious wound healer via MMP dependent pathway. The active pocket docked with indole derivatives at the torsional degree of freedom 0.5 units with Lamarckian genetic algorithm. The inhibitors binding is facilitated by direct hydrogen bond interactions with the residues residing in the catalytic motif of Pseudomonas elastase consisted of Ala113, His140, Glu141, His144, Glu164, Arg198 and His223. In addition, the inhibitors make many hydrophobic interactions with both the enzyme and the co-factor Zinc ion. In view of the possibility that the elastase is an important determinant in Pseudomonas infection, it is conceivable that inhibitors of the enzyme will reduce its destructive effects that may lead to new therapeutic intervention.

DOI 10.11648/j.ajhc.20160201.13
Published in American Journal of Heterocyclic Chemistry (Volume 2, Issue 1, December 2016)
Page(s) 13-19
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2024. Published by Science Publishing Group

Keywords

Fischer Indole, Indium (III) Chloride, EMK, Phenyl Hydrazine Hydrochloride, Molecular Docking, Pseudomonas Elastase

References
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Author Information
  • Department of Chemistry, Jain Institute of Technology, Davanagere, India

  • Department of Micro Biology & Cell biology, Indian Institute of Science, Bengaluru, India

  • Department of Biotechnology, M. S. RIT, Bengaluru, India

  • Department of Chemistry, Jain Institute of Technology, Davanagere, India

  • R&D Center Department of Chemistry, Rajarajeswari College of Engineering, Bengaluru, India

  • Department of Chemistry, Kuvempu University, Karnataka, India

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    Sudhakara Aralihalli, Raghavendra Ramappa, Harish Basavanthappa Gowdru, Nataraja Gummanar, Ramesha Sonnappa, et al. (2016). Aqueous Synthesis and Biological Studies of Indole Derivatives. American Journal of Heterocyclic Chemistry, 2(1), 13-19. https://doi.org/10.11648/j.ajhc.20160201.13

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    ACS Style

    Sudhakara Aralihalli; Raghavendra Ramappa; Harish Basavanthappa Gowdru; Nataraja Gummanar; Ramesha Sonnappa, et al. Aqueous Synthesis and Biological Studies of Indole Derivatives. Am. J. Heterocycl. Chem. 2016, 2(1), 13-19. doi: 10.11648/j.ajhc.20160201.13

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    AMA Style

    Sudhakara Aralihalli, Raghavendra Ramappa, Harish Basavanthappa Gowdru, Nataraja Gummanar, Ramesha Sonnappa, et al. Aqueous Synthesis and Biological Studies of Indole Derivatives. Am J Heterocycl Chem. 2016;2(1):13-19. doi: 10.11648/j.ajhc.20160201.13

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  • @article{10.11648/j.ajhc.20160201.13,
      author = {Sudhakara Aralihalli and Raghavendra Ramappa and Harish Basavanthappa Gowdru and Nataraja Gummanar and Ramesha Sonnappa and Mahadevan Kittappa Malavalli},
      title = {Aqueous Synthesis and Biological Studies of Indole Derivatives},
      journal = {American Journal of Heterocyclic Chemistry},
      volume = {2},
      number = {1},
      pages = {13-19},
      doi = {10.11648/j.ajhc.20160201.13},
      url = {https://doi.org/10.11648/j.ajhc.20160201.13},
      eprint = {https://download.sciencepg.com/pdf/10.11648.j.ajhc.20160201.13},
      abstract = {One pot with expedient approach to the synthesis of 2,3-disubstituted indole derivatives using indium (III) trichloride through Fisher indole method has been developed, in aqueous media. The synthesized compounds were screened for their anti analgesic and antibacterial activity. All the six indole derivatives exhibited significant antibacterial activity against Pseudomonas aeruginosa when compared to standard drug Ciprofloxacin. Based on the results of antibacterial activity, the molecular docking of all six indole derivatives were performed against Pseudomonas elastase a matrix metalloproteinase from Pseudomonas aeruginosa were presumed as an infectious wound healer via MMP dependent pathway. The active pocket docked with indole derivatives at the torsional degree of freedom 0.5 units with Lamarckian genetic algorithm. The inhibitors binding is facilitated by direct hydrogen bond interactions with the residues residing in the catalytic motif of Pseudomonas elastase consisted of Ala113, His140, Glu141, His144, Glu164, Arg198 and His223. In addition, the inhibitors make many hydrophobic interactions with both the enzyme and the co-factor Zinc ion. In view of the possibility that the elastase is an important determinant in Pseudomonas infection, it is conceivable that inhibitors of the enzyme will reduce its destructive effects that may lead to new therapeutic intervention.},
     year = {2016}
    }
    

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  • TY  - JOUR
    T1  - Aqueous Synthesis and Biological Studies of Indole Derivatives
    AU  - Sudhakara Aralihalli
    AU  - Raghavendra Ramappa
    AU  - Harish Basavanthappa Gowdru
    AU  - Nataraja Gummanar
    AU  - Ramesha Sonnappa
    AU  - Mahadevan Kittappa Malavalli
    Y1  - 2016/12/27
    PY  - 2016
    N1  - https://doi.org/10.11648/j.ajhc.20160201.13
    DO  - 10.11648/j.ajhc.20160201.13
    T2  - American Journal of Heterocyclic Chemistry
    JF  - American Journal of Heterocyclic Chemistry
    JO  - American Journal of Heterocyclic Chemistry
    SP  - 13
    EP  - 19
    PB  - Science Publishing Group
    SN  - 2575-5722
    UR  - https://doi.org/10.11648/j.ajhc.20160201.13
    AB  - One pot with expedient approach to the synthesis of 2,3-disubstituted indole derivatives using indium (III) trichloride through Fisher indole method has been developed, in aqueous media. The synthesized compounds were screened for their anti analgesic and antibacterial activity. All the six indole derivatives exhibited significant antibacterial activity against Pseudomonas aeruginosa when compared to standard drug Ciprofloxacin. Based on the results of antibacterial activity, the molecular docking of all six indole derivatives were performed against Pseudomonas elastase a matrix metalloproteinase from Pseudomonas aeruginosa were presumed as an infectious wound healer via MMP dependent pathway. The active pocket docked with indole derivatives at the torsional degree of freedom 0.5 units with Lamarckian genetic algorithm. The inhibitors binding is facilitated by direct hydrogen bond interactions with the residues residing in the catalytic motif of Pseudomonas elastase consisted of Ala113, His140, Glu141, His144, Glu164, Arg198 and His223. In addition, the inhibitors make many hydrophobic interactions with both the enzyme and the co-factor Zinc ion. In view of the possibility that the elastase is an important determinant in Pseudomonas infection, it is conceivable that inhibitors of the enzyme will reduce its destructive effects that may lead to new therapeutic intervention.
    VL  - 2
    IS  - 1
    ER  - 

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