1-H-Indole-3-Glyoxamide Derivatives as Structurally Novel Bacterial Quorum Sensing Inhibitors; Molecular Docking, Admet Analysis, Design, Synthesis and Biological Evaluation

Authors

  • Dr. Bhavesh. L. Dodiya  Department of Chemistry, Shri R. R. Lalan College, bhuj, Gujarat, India
  • Dr. Haresh. K. Ram  Department of Chemistry, Tolani College of Arts & Science, Adipur, Gujarat, India
  • Dr. Govind J Kher  Department of Chemistry, Tolani College of Arts & Science, Adipur, Gujarat, India
  • Dr. Kaushik Joshi  Shree DKV Arts & Science College Jamnagar, Gujarat, India.
  • Ram Nandaniya  R. G. Shah Science College, Ahmedabad, Gujarat, India.
  • Janaki H. Chauhan  Department of Chemistry, Shri R. R. Lalan College, bhuj, Gujarat, India

Keywords:

1-H-indole-3-glyoxamide, antimicrobial, 1-benzyl-1H-indole-2-carboxylic acid, oxalyl chloride.

Abstract

Formulation of an unusual series of 1-benzyl-3-(substituted secondary amine-2- oxoacetyl)-1H-indole-2-carboxylic acid (4a-j) was achieved from 1-benzyl-1H- indole-2-carboxylic acid, oxalyl chloride and secondary amine and few amounts of DCM with 0 to 3 0C after half and hrs the product obtained. All these Modern prepared compounds were characterized by the Mass spectrometry, IR spectroscopy, and 1H-NMR spectroscopy and elemental analyses. Antibacterial and antifungal resistance checks were carried out for newly synthesized compounds.

References

  1. Raj K.M., Mruthyunjayaswamy B.H.M., (2017). Synthesis, spectroscopic characterization, electrochemistry and biological activity evaluation of some metal(II) complexes with ONO donor ligands containing indole and coumarin moieties, J. Saudi Chem. Soc. 21: S202-S218. doi.org/10.1016/j.jscs.2014.01.001
  2. Lamelas R., Fernandez-Lodeiro A., Bastida R., Labisbal E., Macías A., Núnez, ~ C. Lodeiro C., Yanez M., (2017). Novel di-substituted hexaaza-macrocyclic ligands ~ bearing hydrazine and/or indole arms: synthesis, sensor properties and catalytic activity, Inorg. Chim.Acta 456: 34-43. doi.org/10.1016/j.ica.2016.10.047
  3. Ibrahim A.A., Khaledi H., Ali H.M., (2014). A multiproticindole-based thiocarbohydrazone in the formation of mono-, di- and hexa-nuclear metal complexes, Polyhedron 81: 457-464. doi.org/10.1016/j.poly.2014.06.057
  4. Ozdemir A., Alt?ntop M.D., Turan-Zitouni G., Çiftçi G.A., Ertorun I., Alatas O., Kaplanc?kl? Z.A., (2015). Synthesis and evaluation of new indole-based chalcones as potential antiinflammatory agents, Eur. J. Med. Chem. 89: 304-309. DOI: 10.1016/j.ejmech.2014.10.056
  5. Sharma V., Kumar P., Pathak D., (2010). Biological importance of the indole nucleus in recent years: a Comprehensive review, J. Heterocycl. Chem. 47: 491-502. doi.org/10.1002/jhet.349
  6. Singh N., Bhati S.K., Kumar A., (2008). Thiazolyl/oxazolylformazanylindoles as potent anti-inflammatory agents, Eur. J. Med. Chem. 43: 2597-2609. DOI: 10.1016/j.ejmech.2007.12.024
  7. Baharfar R., Asghari S., Kiani M., (2015). Regioselective synthesis and antibacterial activity of 3-(cyanoacetyl) indole-based kojic acid derivatives, Monatshefte Chem. 146: 335-343. doi.org/10.1007/s00706-014-1310-x
  8. Bal T.R., Anand B., Yogeeswari P., Sriram D., (2005), Synthesis and evaluation of antiHIV activity of isatin b-thiosemicarbazone derivatives, Bioorg. Med. Chem. Lett, 15: 4451-4455. DOI: 10.1016/j.bmcl.2005.07.046
  9. Radwan M.A.A., Ragab E.A., Sabry N.M., Shenawy S.M.E., (2007). Synthesis and biological .evaluation of new 3-substituted indole derivatives as potential antiinflammatory and analgesic agents, Bioorg. Med. Chem. 15: 3832-3841. DOI: 10.1016/j.bmc.2007.03.024
  10. Bhale P.S., Chavan H.V., Dongare S.B., Shringare S.N., NMule Y.B., Agane S.S., Bandgar B.P., (2017). Synthesis of extended conjugated indolyl chalcones as potent anti-breast cancer, anti-inflammatory and antioxidant agents, Bioorg. Med. Chem. Lett 27: 1502-1507. DOI: 10.1016/j.bmcl.2017.02.052
  11. Adwas A.A., Elkhoely A.A., Kabel A.M., Abdel-Rahman M.N., Eissa A.A., (2016). Anticancer and cardioprotective effects of indol-3-carbinol in doxorubicin-treated mice, J. Infect. Chemother. 22: 36-43. DOI: 10.1016/j.jiac.2015.10.001
  12. Guan Q., Xing Y., Liu J., Wei W., Zhang R., Wang X., Bai F., (2013). Application of multiple parallel perfused microbioreactors: synthesis, characterization and cytotoxicity testing of the novel rare earth complexes with indole acid as a ligand, J. Inorg. Biochem. 128: 57-67. DOI: 10.1016/j.jinorgbio.2013.07.018
  13. Abdulghani A.J., Hussain R.K., (2015). Synthesis and characterization of Schiff Base metal complexes derived from cefotaxime with 1H-indole-2,3-dione (Isatin) and 4-N,N-dimethyl-aminobenzaldehyde, Open J. Inorg. Chem. 5: 83-101. DOI: 10.4236/ojic.2015.54010
  14. Zhang M., Chen Q., Yang G., (2015). A review on recent developments of indole containing antiviral agents, Eur. J. Med. Chem. 89: 421-441. DOI: 10.1016/j.ejmech.2014.10.065
  15. Dhanaraj C.J., Johnson J., (2017). DNA interaction, antioxidant and in vitro cytotoxic activities of some mononuclear metal(II) complexes of a bishydrazone ligand, Mater. Sci. Eng. C78: 1006-1015. DOI: 10.1016/j.msec.2017.04.152

International Journal of Scientific Research in Chemistry

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Published

2024-01-31

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Volume 9, Issue 1, January-February-2024

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Research Articles

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How to Cite

[1]
Dr. Bhavesh. L. Dodiya, Dr. Haresh. K. Ram, Dr. Govind J Kher, Dr. Kaushik Joshi, Ram Nandaniya, Janaki H. Chauhan, " 1-H-Indole-3-Glyoxamide Derivatives as Structurally Novel Bacterial Quorum Sensing Inhibitors; Molecular Docking, Admet Analysis, Design, Synthesis and Biological Evaluation, International Journal of Scientific Research in Chemistry(IJSRCH), ISSN : 2456-8457, Volume 9, Issue 1, pp.22-32, January-February-2024.