Hydrazone-tethered 5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol hybrids: synthesis, characterisation, in silico ADME studies, and in vitro antimycobacterial evaluation and cytotoxicity

Hydrazone-tethered 5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol hybrids: synthesis, characterisation, in silico ADME studies, and in vitro antimycobacterial evaluation and cytotoxicity. Oderinlo, O. O, Jordaan, A., Seldon, R., Isaacs, M., Hoppe, H. C, Warner, D. F, Tukulula, M., & Khanye, S. D ChemMedChem, John Wiley & Sons, Ltd, 2023.

Paper doi abstract bibtex

Compounds containing arylpyrrole-, 1,2,4-triazole- and hydrazone structural frameworks have been widely studied and demonstrated to exhibit a wide range of pharmacological properties. Herein, an exploratory series of new 1,2,4-triazole derivatives designed by amalgamation of arylpyrrole and 1,2,4-triazole structural units via a hydrazone linkage is reported. The synthesised compounds were tested in vitro for their potential activity against Mycobacterium tuberculosis (MTB) H37Rv strain. The most promising compound 13 – the derivative without the benzene ring appended to the pyrrole unit displayed acceptable activity (MIC90=3.99 $μ$M) against MTB H37Rv, while other compounds from the series exhibited modest to weak antimycobacterial activity with MIC90 values in the range between 7.0 and \textgreater125 $μ$M. Furthermore, in silico results, predicated using the SwissADME web tool, show that the prepared compounds display desirable ADME profile with parameters within acceptable range.

@article{Oderinlo2023,
abstract = {Compounds containing arylpyrrole-, 1,2,4-triazole- and hydrazone structural frameworks have been widely studied and demonstrated to exhibit a wide range of pharmacological properties. Herein, an exploratory series of new 1,2,4-triazole derivatives designed by amalgamation of arylpyrrole and 1,2,4-triazole structural units via a hydrazone linkage is reported. The synthesised compounds were tested in vitro for their potential activity against Mycobacterium tuberculosis (MTB) H37Rv strain. The most promising compound 13 – the derivative without the benzene ring appended to the pyrrole unit displayed acceptable activity (MIC90=3.99 $\mu$M) against MTB H37Rv, while other compounds from the series exhibited modest to weak antimycobacterial activity with MIC90 values in the range between 7.0 and {\textgreater}125 $\mu$M. Furthermore, in silico results, predicated using the SwissADME web tool, show that the prepared compounds display desirable ADME profile with parameters within acceptable range.},
author = {Oderinlo, Ogunyemi O and Jordaan, Audrey and Seldon, Ronnett and Isaacs, Michelle and Hoppe, Heinrich C and Warner, Digby F and Tukulula, Matshawandile and Khanye, Setshaba D},
doi = {10.1002/CMDC.202200572},
file = {:C$\backslash$:/Users/01462563/AppData/Local/Mendeley Ltd./Mendeley Desktop/Downloaded/Oderinlo et al. - 2023 - Hydrazone-tethered 5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol hybrids synthesis, characterisation, in silico AD.pdf:pdf},
issn = {1860-7187},
journal = {ChemMedChem},
keywords = {1,2,4-Triazoles.,Arylpyrroles,Hydrazone,Molecular hybridisation,Mycobacterium tuberculosis,OA,fund{\_}not{\_}ack,original},
mendeley-tags = {OA,fund{\_}not{\_}ack,original},
pages = {e202200572},
pmid = {36617507},
publisher = {John Wiley {\&} Sons, Ltd},
title = {{Hydrazone-tethered 5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol hybrids: synthesis, characterisation, \textit{in silico} ADME studies, and \textit{in vitro} antimycobacterial evaluation and cytotoxicity}},
url = {https://onlinelibrary.wiley.com/doi/full/10.1002/cmdc.202200572 https://onlinelibrary.wiley.com/doi/abs/10.1002/cmdc.202200572 https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cmdc.202200572},
year = {2023}
}

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