European Journal of Chemistry

Synthesis, molecular docking, and biological evaluation of methyl-5-(hydroxyimino)-3-(aryl-substituted)hexanoate derivatives

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Published: Jun 30, 2022
DOI: https://doi.org/10.5155/eurjchem.13.2.151-161.2220
Keywords:
Cytotoxic, Antioxidant activity, Antibacterial activity, Anti-inflammatory activity, Beta-aryl ketohexanoic acid, Hydroxylamine hydrochloride
Section
Research Article
Issue
Vol. 13 No. 2 (2022): June 2022
Dates
Received 2021-12-10
Accepted 2022-04-03
Published 2022-06-30
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Parashuram Gudimani
Department of Chemistry, Karnatak University, Dharwad 580003, Karnataka, India
https://orcid.org/0000-0002-3131-1958
Samundeeswari Lokesh Shastri
Department of Chemistry, Karnatak University, Dharwad 580003, Karnataka, India
https://orcid.org/0000-0003-1035-7081
Varsha Pawar
Department of Chemistry, Karnatak University, Dharwad 580003, Karnataka, India
https://orcid.org/0000-0003-2096-9356
Nagashree Uday Hebbar
Department of Chemistry, Karnatak University, Dharwad 580003, Karnataka, India
https://orcid.org/0000-0002-8647-2724
Lokesh Anand Shastri
Department of Chemistry, Karnatak University, Dharwad 580003, Karnataka, India
https://orcid.org/0000-0002-5672-8442
Shrinivas Joshi
Novel Drug Design and Discovery Laboratory, Department of Pharmaceutical Chemistry, Soniya Education Trusts College of Pharmacy, SangolliRayanna Nagar, Dharwad 580002, Karnataka, India
https://orcid.org/0000-0002-6520-806X
Shyam Kumar Vootla
Department of Biotechnology and Microbiology, Karnatak University, Dharwad 580003, Karnataka, India
https://orcid.org/0000-0002-7936-9825
Sheela Khanapure
Department of Biotechnology and Microbiology, Karnatak University, Dharwad 580003, Karnataka, India
https://orcid.org/0000-0002-4247-1658
Vinay Sunagar
Department of Chemistry, Govindram Seksaria Science College, Belagavi 590006, Karnataka, India
https://orcid.org/0000-0001-9804-7330

Abstract

Beta-aryl keto hexanoic acids (5a-l) were synthesized efficiently, followed by esterification that afforded beta-aryl keto methylhexanoates (6a-l). The chemo-selective ketoxime beta-aryl methyl hexanoates (7a-l) were isolated in good yields. Spectroscopic methods were used to characterize the obtained moieties. The antioxidant, anti-inflammatory, and antibacterial properties of the effectively synthesized compounds 7a-l were also investigated. The anti-inflammatory activity of the compounds 7c, 7f, 7i, and 7l was excellent, with a low IC50 value at micromolar concentration, which was much better than the reference diclofenac. All synthesized compounds 7a-l were assessed for their in vitro antibacterial activity against S. aureus, B. subtilis and E. coli.  Most of the compounds exhibited promising activity against Gram-positive bacterial strain, compound 7i showed excellent activity compared to standard streptomycin and in the case of E. coli, compounds 7b, 7c, 7j, 7k and 7l have shown moderate activity. Further, the cytotoxic activities of the compounds were assessed against lung cancer cells (A549) by using MTT assay. The possible interaction mechanism of the molecules 7c and 7g with Gram-negative strain E. coli DNA gyrase B in complex with PDB ID: 4DUH was studied.


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Gudimani, P.; Shastri, S. L.; Pawar, V.; Hebbar, N. U.; Shastri, L. A.; Joshi, S.; Vootla, S. K.; Khanapure, S.; Sunagar, V. Synthesis, Molecular Docking, and Biological Evaluation of Methyl-5-(hydroxyimino)-3-(aryl-substituted)hexanoate Derivatives. Eur. J. Chem. 2022, 13, 151-161.

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