Synthesis and Primary Biological Evaluation of Triazole‐Modified Picroside II Compounds

Abstract

Picroside II, an iridoid glycoside, has anti‐cancer, anti‐virus, anti‐apoptotic, nervous and myocardial protection effects and so on. However, the oral bioavailability of Picroside II is low, and the half‐life in vivo is short, so it is limited to use in clinic. Triazole is a highly stable heterocyclic ring, which can be interacted with various enzymes or receptors in the organism through non‐covalent interactions, and many of its good pharmacological activities in vitro and in vivo have been reported. Based on the advantages of triazole and Picroside II, a series of triazole‐modified Picroside II derivatives (5 a–5 i) were synthesized by using drug combination principles for the first time. The structures were confirmed by different spectroscopic techniques including 1H NMR, 13C NMR and HRMS, and the primary biological evaluation of anti‐breast cancer, anti‐colorectal cancer, the effect on SARS‐CoV‐2 3CLpro inhibitor, and CD47‐SIRPα protein were screened as well. Compound 5 e has anti‐breast cancer activity, and compounds 3 and 5 i have anti‐colorectal cancer activity.

Design, synthesis and anticancer activities evaluation of novel pyrazole modified catalpol derivatives

“…Based on the previous research foundation of our research group on iridoids 19 , 20 and the anticancer activity of catalpol and pyrazole, a series of pyrazole modified catalpol compounds were synthesized by the principle of drug combination (Fig. 3 ).…”

Design, Synthesis and Biological Evaluation of Novel Catalpol Derivatives as Potential Pancreatic Cancer Inhibitors

“…Therefore, large number of heterocyclic organic molecules of different category and classes in search of their potentials in medicinal chemistry have been explored. [23][24][25][26][27][28][29] Based on our previous studies on the structure-activity relationship and structural modification optimization of iridoids, [30][31][32][33] a series of imidazol-modified catalpol derivatives were synthesized by the method of molecular hybridization. Additionally, the inhibitory activities of these derivatives were in vitro evaluated on the pancreatic cancer cells.…”

“…Based on our previous studies on the structure‐activity relationship and structural modification optimization of iridoids, [30–33] a series of imidazol‐modified catalpol derivatives were synthesized by the method of molecular hybridization. Additionally, the inhibitory activities of these derivatives were in vitro evaluated on the pancreatic cancer cells.…”