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Growing Science » Current Chemistry Letters » Synthesis, antimicrobial activity, DFT-calculation, and docking of 4-(1,3,4-thiadiazol-2-yl)-containing polysubstituted pyrroles

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Current Chemistry Letters

ISSN 1927-730x (Online) - ISSN 1927-7296 (Print)
Quarterly Publication
Volume 13 Issue 4 pp. 761-776 , 2024

Synthesis, antimicrobial activity, DFT-calculation, and docking of 4-(1,3,4-thiadiazol-2-yl)-containing polysubstituted pyrroles Pages 761-776 Right click to download the paper Download PDF

Authors: Sergiy Kemskyi, Alina Grozav, Vitalii Chornous, Nina Yakovychuk, Mariana Fedoriv, Dmytro Melnyk, Oksana Melnyk, Mykhailo Vovk

DOI: 10.5267/j.ccl.2024.3.005

Keywords: 5-Chloro-4-formyl-1H-pyrrole-3-carboxylates, 4-(1, 3, 4-Thiadiazol-2-yl)pyrroles, Antimicrobial activity, DFT calculation, Docking

Abstract: A series of new 4-(1,3,4-thiadiazol-2-yl)-containing polysubstituted pyrroles 3 a-k has been synthesized by a preparative convenient method from ethyl 5-chloro-4-formyl-1H-pyrrole-3-carboxylates 1 a-e, which were selectively transformed into the corresponding polysubstituted pyrrole-4-carboxylic acids 2 а-е using sodium hypochlorite as an oxidizer. Further, they were transformed into the target compounds with a high yield using the cyclocondensation with N-mono- or N,N-disubstituted thiosemicarbazides in the boiling phosphorus trichloroxide. As seen from the screening of antimicrobial activity, the synthesized compounds exhibit the inhibiting and bactericide activity against some bacteria and fungi. The highest activity has been established for the compounds 3 a, c, e-h, j against the strain Klebsiella pneumoniae (МІС=31.25 µg/mL). The calculated HOMO energy level proves that the compound 3 с is the most reactive ligand for the interaction with a protein receptor. The molecular docking data show that the compound 3 h has the highest affinity to the ThiM Klebsiella pneumoniae kinase.

How to cite this paper
Kemskyi, S., Grozav, A., Chornous, V., Yakovychuk, N., Fedoriv, M., Melnyk, D., Melnyk, O & Vovk, M. (2024). Synthesis, antimicrobial activity, DFT-calculation, and docking of 4-(1,3,4-thiadiazol-2-yl)-containing polysubstituted pyrroles.Current Chemistry Letters, 13(4), 761-776.

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Journal: Current Chemistry Letters | Year: 2024 | Volume: 13 | Issue: 4 | Views: 840 | Reviews: 0

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