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Abstract

Design, Synthesis, Molecular Docking Studies, and Biological Evaluation of 1, 3, 4-oxadiazol-3(2H)-yl] Ethan-1-one Derivatives as Antimicrobial Agents †

1
Department of Pharmaceutical Chemistry, SVKM’s Dr. Bhanuben Nanavati College of Pharmacy, Gate No.1, Mithibai College Campus, Vaikunthlal Mehta Rd, Vile Parle West, Mumbai 400056, Maharashtra, India
2
Department of Pharmaceutical Chemistry and Quality Assurance, SVKM’s Dr. Bhanuben Nanavati College of Pharmacy, Gate No.1, Mithibai College Campus, Vaikunthlal Mehta Rd, Vile Parle West, Mumbai 400056, Maharashtra, India
*
Author to whom correspondence should be addressed.
Presented at the 8th International Electronic Conference on Medicinal Chemistry, 1–30 November 2022; Available online: https://ecmc2022.sciforum.net/.
Med. Sci. Forum 2022, 14(1), 143; https://doi.org/10.3390/ECMC2022-13247
Published: 1 November 2022
(This article belongs to the Proceedings of The 8th International Electronic Conference on Medicinal Chemistry)

Abstract

:
A number of novel 1, 3, 4-oxadiazole analogues have been designed and synthesized through the condensation of substituted aldehyde/ketone with substituted benzohydrazide to form substituted N′-alkylidene benzohydrazide and then cyclization of N′-alkylidene benzohydrazide to form 1, 3, 4-oxadiazole derivatives. To investigate the antimicrobial data on a structural basis, in-silico docking studies of the synthesized compounds (4a4r) into the crystal structure of E. coli DNA gyrase (Type-2 topoisomerase) using Autodock PyRx virtual screening program were performed to predict the affinity and orientation of the synthesized compounds at the activities by using 6rks Protein Data Bank (PDB). Inhibiting the ATPase activity of gyrase blocks the introduction of negative supercoils in DNA and traps the chromosome in a positively supercoiled state that may have a downstream impact on cell physiology and division. The results indicate that ketone-substituted benzohydrazide derivatives show good binding affinity (−8 kcal to −9 kcal) and electron-withdrawing group such as –NO2 and –Cl present at R1 increases the affinity of scaffold and DNA gyrase receptors and binds into the specificity pocket. In this pocket, the 1, 3, 4-oxadiazole nucleus of these compounds interacts with the amino acid Alanine A: 421, Valine A: 420, Tyrosine A: 478, and Glutamine A: 381 residues of the target. Also, it is verified by in vitro antimicrobial screening, where all the compounds were active against tested bacterial strains. Among these compounds 4(c), 4(d), (4e), (4h), (4i), 4(m), 4(n), 4(o), 4(p), and (4q) showed good bacterial zone inhibition.

Supplementary Materials

The following are available online at https://www.mdpi.com/article/10.3390/ECMC2022-13247/s1.

Author Contributions

Conceptualization: T.K.; Methodology: R.L. and T.K.; Writing—originaldraft preparation: R.L.; Writing—review and editing: R.L. All authors have read and agreed to the published version of the manuscript.

Funding

This research received no external funding.

Institutional Review Board Statement

This study did not require any approval from Ethical committee.

Informed Consent Statement

Not applicable.

Data Availability Statement

Not applicable.

Conflicts of Interest

The authors declare no conflict of interest.
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Share and Cite

MDPI and ACS Style

Likhar, R.; Khan, T. Design, Synthesis, Molecular Docking Studies, and Biological Evaluation of 1, 3, 4-oxadiazol-3(2H)-yl] Ethan-1-one Derivatives as Antimicrobial Agents. Med. Sci. Forum 2022, 14, 143. https://doi.org/10.3390/ECMC2022-13247

AMA Style

Likhar R, Khan T. Design, Synthesis, Molecular Docking Studies, and Biological Evaluation of 1, 3, 4-oxadiazol-3(2H)-yl] Ethan-1-one Derivatives as Antimicrobial Agents. Medical Sciences Forum. 2022; 14(1):143. https://doi.org/10.3390/ECMC2022-13247

Chicago/Turabian Style

Likhar, Rupali, and Tabassum Khan. 2022. "Design, Synthesis, Molecular Docking Studies, and Biological Evaluation of 1, 3, 4-oxadiazol-3(2H)-yl] Ethan-1-one Derivatives as Antimicrobial Agents" Medical Sciences Forum 14, no. 1: 143. https://doi.org/10.3390/ECMC2022-13247

APA Style

Likhar, R., & Khan, T. (2022). Design, Synthesis, Molecular Docking Studies, and Biological Evaluation of 1, 3, 4-oxadiazol-3(2H)-yl] Ethan-1-one Derivatives as Antimicrobial Agents. Medical Sciences Forum, 14(1), 143. https://doi.org/10.3390/ECMC2022-13247

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