Version 1
: Received: 30 June 2024 / Approved: 1 July 2024 / Online: 2 July 2024 (00:18:21 CEST)
How to cite:
Aziafor, K.; Rupareila, K.; Zloh, M.; Parish, T.; Brucoli, F. Design and Synthesis of Pyridyl and 2-Hydroxyphenyl Chalcones with Antitubercular Activity.. Preprints2024, 2024070139. https://doi.org/10.20944/preprints202407.0139.v1
Aziafor, K.; Rupareila, K.; Zloh, M.; Parish, T.; Brucoli, F. Design and Synthesis of Pyridyl and 2-Hydroxyphenyl Chalcones with Antitubercular Activity.. Preprints 2024, 2024070139. https://doi.org/10.20944/preprints202407.0139.v1
Aziafor, K.; Rupareila, K.; Zloh, M.; Parish, T.; Brucoli, F. Design and Synthesis of Pyridyl and 2-Hydroxyphenyl Chalcones with Antitubercular Activity.. Preprints2024, 2024070139. https://doi.org/10.20944/preprints202407.0139.v1
APA Style
Aziafor, K., Rupareila, K., Zloh, M., Parish, T., & Brucoli, F. (2024). Design and Synthesis of Pyridyl and 2-Hydroxyphenyl Chalcones with Antitubercular Activity.. Preprints. https://doi.org/10.20944/preprints202407.0139.v1
Chicago/Turabian Style
Aziafor, K., Tanya Parish and Federico Brucoli. 2024 "Design and Synthesis of Pyridyl and 2-Hydroxyphenyl Chalcones with Antitubercular Activity." Preprints. https://doi.org/10.20944/preprints202407.0139.v1
Abstract
A focussed library of pyridyl and 2-hydroxyphenyl chalcones were synthesized and tested for growth inhibitory activity against Mycobacterium tuberculosis H37Rv, and normal and cancer breast cell lines. Pyridyl chalcones bearing lipophilic A-ring, e.g., dichloro-phenyl- (14), pyrene-1-yl (20)- and biphenyl-4-yl (21) moieties, were found to be the most potent of the series inhibiting the growth of M. tuberculosis H37Rv with IC90 values ranging from 8.9 – 28 µM. Aryl chalcones containing a 3-methoxyphenyl A-ring and either p-Br-phenyl (25) or p-Cl- phenyl (26) B-rings showed an IC90 value of 28 μM. Aryl-chalcones were generally less toxic to HepG2 cells compared to pyridyl-chalcones. Dose-dependent antiproliferative activity against MDA468 cells was observed for trimethoxy-phenyl (16) and anthracene-9-yl (19) pyridyl-chalcones with IC50 values of 0.7 and 0.3 µM, respectively. Docking studies revealed that chalone 20 was predicted to bind to the M. tuberculosis protein tyrosine phosphatases B (PtpB) with higher affinity compared to a previously reported PtpB inhibitor.
Chemistry and Materials Science, Medicinal Chemistry
Copyright:
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
