Aqueous Synthesis and Biological Studies of Indole Derivatives

Sudhakara Aralihalli; Raghavendra Ramappa; Harish Basavanthappa Gowdru; Nataraja Gummanar; Ramesha Sonnappa; Mahadevan Kittappa Malavalli

doi:doi:10.11648/j.ajhc.20160201.13

Aqueous Synthesis and Biological Studies of Indole Derivatives

Sudhakara Aralihalli, Raghavendra Ramappa, Harish Basavanthappa Gowdru, Nataraja Gummanar, Ramesha Sonnappa, Mahadevan Kittappa Malavalli

Published in American Journal of Heterocyclic Chemistry (Volume 2, Issue 1)

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.

Published in	American Journal of Heterocyclic Chemistry (Volume 2, Issue 1)
DOI	10.11648/j.ajhc.20160201.13
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), 2016. Published by Science Publishing Group

Keywords

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

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APA Style

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://article.sciencepublishinggroup.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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Author Information

Sudhakara Aralihalli

Department of Chemistry, Jain Institute of Technology, Davanagere, India
Raghavendra Ramappa

Department of Micro Biology & Cell biology, Indian Institute of Science, Bengaluru, India
Harish Basavanthappa Gowdru

Department of Biotechnology, M. S. RIT, Bengaluru, India
Nataraja Gummanar

Department of Chemistry, Jain Institute of Technology, Davanagere, India
Ramesha Sonnappa

R&D Center Department of Chemistry, Rajarajeswari College of Engineering, Bengaluru, India
Mahadevan Kittappa Malavalli

Department of Chemistry, Kuvempu University, Karnataka, India

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APA Style

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://article.sciencepublishinggroup.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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