Version 1
: Received: 31 October 2024 / Approved: 31 October 2024 / Online: 31 October 2024 (18:24:00 CET)
How to cite:
Aijijiyah, N. P.; Fadlan, A.; Ningsih, S.; Santoso, M. 5-Bromo-N'-(2-oxoindolin-3-ylidene)furan-2-carbohydrazide. Preprints2024, 2024102609. https://doi.org/10.20944/preprints202410.2609.v1
Aijijiyah, N. P.; Fadlan, A.; Ningsih, S.; Santoso, M. 5-Bromo-N'-(2-oxoindolin-3-ylidene)furan-2-carbohydrazide. Preprints 2024, 2024102609. https://doi.org/10.20944/preprints202410.2609.v1
Aijijiyah, N. P.; Fadlan, A.; Ningsih, S.; Santoso, M. 5-Bromo-N'-(2-oxoindolin-3-ylidene)furan-2-carbohydrazide. Preprints2024, 2024102609. https://doi.org/10.20944/preprints202410.2609.v1
APA Style
Aijijiyah, N. P., Fadlan, A., Ningsih, S., & Santoso, M. (2024). 5-Bromo-N'-(2-oxoindolin-3-ylidene)furan-2-carbohydrazide. Preprints. https://doi.org/10.20944/preprints202410.2609.v1
Chicago/Turabian Style
Aijijiyah, N. P., Sri Ningsih and Mardi Santoso. 2024 "5-Bromo-N'-(2-oxoindolin-3-ylidene)furan-2-carbohydrazide" Preprints. https://doi.org/10.20944/preprints202410.2609.v1
Abstract
5-Bromo-N'-(2-oxoindolin-3-ylidene)furan-2-carbohydrazide (1) was successfully synthesized in 81% yield from commercially available isatin and 5-bromofuran-2-carbohydrazide in acidic conditions under reflux. The structure of synthesized compound 1 was confirmed by 1H and 13C NMR, FTIR, and HRMS spectrometers. This study used in vitro models to investigate the anti-inflammatory activity of compound 1, which included the inhibition of BSA denaturation, proteinase activity, and heat- and hypotonicity-induced hemolysis. Compound 1 displayed an inhibitory effect comparable to the standard drug diclofenac sodium. Compound 1 inhibited 50% of BSA denaturation, proteinase activity, and heat- and hypotonicity-induced hemolysis at concentrations of 3.54, 3.04, 2.25, and 1.82, respectively, while diclofenac sodium was 1.99, 3.38, 2.28, and 2.00 μg/mL, respectively. Furthermore, compound 1 was considered a drug-like candidate with no violation of Lipinski’s rule of five, had good ADME properties, and did not show any toxic properties. A molecular docking study of compound 1 (binding energy -9.63 kcal/mol) revealed that compound 1 occupied a unique channel of the cyclooxygenase active site, contributed to the specificity of COX-2 protein, and interacted with some channel hydrophobic residues. These findings indicated that compound 1 has the potential to be optimized into an anti-inflammatory agent.
Keywords
synthesis; in vitro anti-inflammatory activity; molecular docking; disease
Subject
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.
