Synthesis, Cytotoxicity, and α-glucosidase Inhibitory Activity of Triterpenic and Sitosterol Tetrazole Derivatives

Acetylcholinesterase Inhibitory Activity of Modified Lupane, Oleanane, and Ursane A‐seco‐Triterpenoids

“…The structures of the previously synthesized derivatives of lupane 3 , 5 – 8 and oleanane 1 , 2 , 4 types are presented in Figure 1 [18,20–23] . Advances in the synthesis of triterpenes derivatives with modified A‐ring indicated their high potential as therapeutic agents for the treatment of cancer and other diseases [24] .…”

“…Although allobetulin derivatives are known for acting as inhibitors of cholinesterases, [25] there was still no information about the AChE inhibitory activity of their 28‐oxo‐derivatives. Finally, some studies confirm that compounds containing such groups as bromo‐, azido‐, oxazolyl, and alkynyl display cytotoxic activity, tetrazolyl‐derivatives are able to inhibit of alfa‐glucosidase, thus allowing us to conclude that these fragments can play the role of a pharmacophore [18,20–23] . Therefore, A‐ seco ‐28‐oxo‐allobetulins with bromo‐, azido‐ and tetrazolyl‐fragments were used.…”

“…The structures of the previously synthesized derivatives of lupane 3, 5-8 and oleanane 1, 2, 4 types are presented in Figure 1. [18,[20][21][22][23] Advances in the synthesis of triterpenes derivatives with modified A-ring indicated their high potential as therapeutic agents for the treatment of cancer and other diseases. [24] At the same time, despite extensive data on the inhibition of various enzymes by triterpenoids, information on the inhibition of cholinester derivatives with a fragmented ring A is limited.…”

“…Finally, some studies confirm that compounds containing such groups as bromo-, azido-, oxazolyl, and alkynyl display cytotoxic activity, tetrazolyl-derivatives are able to inhibit of alfa-glucosidase, thus allowing us to conclude that these fragments can play the role of a pharmacophore. [18,[20][21][22][23] Therefore, A-seco-28-oxo-allobetulins with bromo-, azido-and tetrazolyl-fragments were used. In addition, derivatives based on A-seco-betulinic acid holding the same functional groups were also implemented into this work.…”

“…[8] At the same time, data on the inhibitory properties of A-seco-triterpenoids toward BChE and AChE in comparison to their ability to act against α-glucosidase are limited. [18] We have previously shown that the structural modifications of the A-ring by the Beckmann rearrangement have a high impact on the inhibitory potential for cholinesterases. [19] For example, azepano-11-deoxy-glycyrrhetol inhibits BChE with K i value 0.21 μM.…”