European Journal of Chemistry 2022, 13(2), 151-161 | doi: https://doi.org/10.5155/eurjchem.13.2.151-161.2220 | Get rights and content

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


Parashuram Gudimani (1) orcid , Samundeeswari Lokesh Shastri (2,*) orcid , Varsha Pawar (3) orcid , Nagashree Uday Hebbar (4) orcid , Lokesh Anand Shastri (5) orcid , Shrinivas Joshi (6) orcid , Shyam Kumar Vootla (7) orcid , Sheela Khanapure (8) orcid , Vinay Sunagar (9) orcid

(1) Department of Chemistry, Karnatak University, Dharwad 580003, Karnataka, India
(2) Department of Chemistry, Karnatak University, Dharwad 580003, Karnataka, India
(3) Department of Chemistry, Karnatak University, Dharwad 580003, Karnataka, India
(4) Department of Chemistry, Karnatak University, Dharwad 580003, Karnataka, India
(5) Department of Chemistry, Karnatak University, Dharwad 580003, Karnataka, India
(6) Novel Drug Design and Discovery Laboratory, Department of Pharmaceutical Chemistry, Soniya Education Trusts College of Pharmacy, SangolliRayanna Nagar, Dharwad 580002, Karnataka, India
(7) Department of Biotechnology and Microbiology, Karnatak University, Dharwad 580003, Karnataka, India
(8) Department of Biotechnology and Microbiology, Karnatak University, Dharwad 580003, Karnataka, India
(9) Department of Chemistry, Govindram Seksaria Science College, Belagavi 590006, Karnataka, India
(*) Corresponding Author

Received: 10 Dec 2021 | Revised: 22 Mar 2022 | Accepted: 03 Apr 2022 | Published: 30 Jun 2022 | Issue Date: June 2022

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.


Keywords


Cytotoxic; Antioxidant activity; Antibacterial activity; Anti-inflammatory activity; Beta-aryl ketohexanoic acid; Hydroxylamine hydrochloride

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DOI: 10.5155/eurjchem.13.2.151-161.2220

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The Department of Science and Technology and UGC-UPE, New Delhi, India.

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How to cite


Gudimani, P.; Shastri, S.; Pawar, V.; Hebbar, N.; Shastri, L.; Joshi, S.; Vootla, S.; Khanapure, S.; Sunagar, V. Eur. J. Chem. 2022, 13(2), 151-161. doi:10.5155/eurjchem.13.2.151-161.2220
Gudimani, P.; Shastri, S.; Pawar, V.; Hebbar, N.; Shastri, L.; Joshi, S.; Vootla, S.; Khanapure, S.; Sunagar, V. Synthesis, molecular docking, and biological evaluation of methyl-5-(hydroxyimino)-3-(aryl-substituted)hexanoate derivatives. Eur. J. Chem. 2022, 13(2), 151-161. doi:10.5155/eurjchem.13.2.151-161.2220
Gudimani, P., Shastri, S., Pawar, V., Hebbar, N., Shastri, L., Joshi, S., Vootla, S., Khanapure, S., & Sunagar, V. (2022). Synthesis, molecular docking, and biological evaluation of methyl-5-(hydroxyimino)-3-(aryl-substituted)hexanoate derivatives. European Journal of Chemistry, 13(2), 151-161. doi:10.5155/eurjchem.13.2.151-161.2220
Gudimani, Parashuram, Samundeeswari Lokesh Shastri, Varsha Pawar, Nagashree Uday Hebbar, Lokesh Anand Shastri, Shrinivas Joshi, Shyam Kumar Vootla, Sheela Khanapure, & Vinay Sunagar. "Synthesis, molecular docking, and biological evaluation of methyl-5-(hydroxyimino)-3-(aryl-substituted)hexanoate derivatives." European Journal of Chemistry [Online], 13.2 (2022): 151-161. Web. 19 Aug. 2022
Gudimani, Parashuram, Shastri, Samundeeswari, Pawar, Varsha, Hebbar, Nagashree, Shastri, Lokesh, Joshi, Shrinivas, Vootla, Shyam, Khanapure, Sheela, AND Sunagar, Vinay. "Synthesis, molecular docking, and biological evaluation of methyl-5-(hydroxyimino)-3-(aryl-substituted)hexanoate derivatives" European Journal of Chemistry [Online], Volume 13 Number 2 (30 June 2022)

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