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New ursolic acid derivatives bearing 1,2,3-triazole moieties: design, synthesis and anti-inflammatory activity in vitro and in vivo

In order to discover novel anti-inflammatory agents, three series of compounds obtained by appending 1,2,3-triazole moieties on ursolic acid were designed and synthesized. All compounds have been screened for their anti-inflammatory activity by using an ear edema model. The potent anti-inflammatory...

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Bibliographic Details
Published in:Molecular diversity 2022-04, Vol.26 (2), p.1129-1139
Main Authors: Zhang, Tian-Yi, Li, Chun-Shi, Cao, Li-Ting, Bai, Xue-Qian, Zhao, Dong-Hai, Sun, Si-Mei
Format: Article
Language:English
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Summary:In order to discover novel anti-inflammatory agents, three series of compounds obtained by appending 1,2,3-triazole moieties on ursolic acid were designed and synthesized. All compounds have been screened for their anti-inflammatory activity by using an ear edema model. The potent anti-inflammatory compound was subjected to in vitro cyclooxygenase COX-1/COX-2 inhibition assays. In general, the derivatives were found to be potent anti-inflammatory activity. Especially, the compound 11b exhibited the strongest activity of all of the compounds prepared, with 82.81% inhibition after intraperitoneal administration, which was better than celecoxib as a positive control. Molecular docking results unclose the rationale for the interaction of the compound 11b with COX-2 enzyme. Further studies revealed that compound 11b exhibited effective COX-2 inhibitory activity, with half-maximal inhibitor concentration (IC 50 ) value of 1.16 µM and selectivity index (SI = 64.66) value close to that of celecoxib (IC 50  = 0.93 µM, SI = 65.47). Taken together, these results could suggest a promising chemotype for development of new COX-2-targeting anti-inflammatory agent. Graphic abstract
ISSN:1381-1991
1573-501X
DOI:10.1007/s11030-021-10236-0