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Computer-Aided Discovery of Anti-Inflammatory Thiazolidinones with Dual Cyclooxygenase/Lipoxygenase Inhibition
Open accessAbstract
New anti-inflammatory agents possessing dual cyclooxygenase/lipoxygenase (COX/LOX) inhibition were discovered by computer-aided prediction of biological activity for 573 virtually designed chemical compounds. Prediction of biological activity was performed by PASS, and prediction results were analyzed with PharmaExpert software. Nine 2-(thiazole-2-ylamino)-5-phenylidene-4-thiazolidinone derivatives differing by the phenyl group substitution were selected for synthesis and experimental testing as potential COX/LOX inhibitors. Eight tested compounds exhibited anti-inflammatory activity in the carrageenin-induced paw edema. It was shown that seven tested compounds (77.8%) were LOX inhibitors, seven compounds were COX inhibitors (77.8%), and six tested compounds (66.7%) were dual COX/LOX inhibitors. Analysis of lipophilicity of the compounds showed a negative correlation with inhibition of edema formation. The binding modes of the most active compounds of this series (2-(thiazole-2-ylamino)-5-( m-chlorophenylidene)-4-thiazolidinone for COX-1 and COX-2, and 2-(thiazole-2-ylamino)-5-( m-nitrophenylidene)-4-thiazolidinone for 15-LOX) were proposed on the basis of docking studies.
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Development and validation of a genetic algorithm for flexible docking 1 1Edited by F. E. Cohen
Jones, G., Willett, P., Glen, R. C., Leach, A. R., & Taylor, R. (1997) · Journal of Molecular Biology · doi:10.1006/jmbi.1996.0897 · Cited by 6,763
Charifson, P. S., Corkery, J. J., Murcko, M. A., & Walters, W. P. (1999) · Journal of Medicinal Chemistry · doi:10.1021/jm990352k · Cited by 698
Cited by
Rao, P., & Knaus, E. E. (2008) · Journal of Pharmacy & Pharmaceutical Sciences · doi:10.18433/j3t886 · Cited by 773
Halogen atoms in the modern medicinal chemistry: hints for the drug design
Hernandes, M., Cavalcanti, S. M., Moreira, D. R., de Azevedo Junior, W., & Leite, A. C. (2010) · Current Drug Targets · doi:10.2174/138945010790711996 · Cited by 723
Recent developments and biological activities of thiazolidinone derivatives: A review
Jain, A. K., Vaidya, A., Ravichandran, V., Kashaw, S. K., & Agrawal, R. K. (2012) · Bioorganic & Medicinal Chemistry · doi:10.1016/j.bmc.2012.03.069 · Cited by 461
Medicinal significance of benzothiazole scaffold: an insight view
Sharma, P. C., Sinhmar, A., Sharma, A., Rajak, H., & Pathak, D. P. (2013) · Journal of Enzyme Inhibition and Medicinal Chemistry · doi:10.3109/14756366.2012.720572 · Cited by 256
Multi-Targeted Natural Products Evaluation Based on Biological Activity Prediction with PASS
Lagunin, A., Filimonov, D., & Poroikov, V. (2010) · Current Pharmaceutical Design · doi:10.2174/138161210791164063 · Cited by 179
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Metadata
- Authors
- Geronikaki, A. A., Lagunin, A. A., Hadjipavlou-Litina, D. I., Eleftheriou, P. T., Filimonov, D. A., Poroikov, V. V., Alam, I., & Saxena, A. K.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2008-02-27
- Volume
- 51
- Issue
- 6
- Pages
- 1601-1609
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W1983432132
- Cited by
- 176
- References
- 2
- FWCI
- 16.55
- Type
- journal article
- Language
- en
- Open access
- green
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- Geronikaki, A. A., Lagunin, A. A., Hadjipavlou-Litina, D. I., Eleftheriou, P. T., Filimonov, D. A., Poroikov, V. V., Alam, I., & Saxena, A. K. (2008). Computer-Aided Discovery of Anti-Inflammatory Thiazolidinones with Dual Cyclooxygenase/Lipoxygenase Inhibition. Journal of Medicinal Chemistry. https://doi.org/10.1021/jm701496h
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