Synthesis of O- and N-Aminopropyltriterpenoids Based on Messagenin

From Marine Metabolites to the Drugs of the Future: Squalamine, Trodusquemine, Their Steroid and Triterpene Analogues

“…tent micromolar inhibitor of yeast α-glucosidase and simultaneously inhibit endosomal reticulum α-glucosidase, rendering it potentially capable to suppress tumor invasiveness and neovascularization in addition to the direct cytotoxicity [265]. Using the described approach, 3β,20R,28-tri-(3-aminopropoxy)-betulin 240 [266,267] and 2-cyanoethoxy-241 and 3-aminopropoxy-betulinic N-methylpiperazinylamide 242 were synthesized and showed highly cytotoxic activities towards non-small cell lung, colon, breast, ovarian, leukemia, renal, melanoma, prostate and CNS cancer cells [264,268]. Triterpenoids with alkane polyamine fragments in the C28 side chain were synthesized on the basis of betulonic and oleanonic acids 243, 244.…”

“…), MeOH, 20 °С, 12 h; NaBH4 (2 eq. ), −78 °С, 2 h. Among triterpene-based polyamines, the most representative group is presented by triterpenic conjugates with linear and cyclic diamines 267-299 (Figure 11) [263][264][265]267,. The reactions involved both native acids and their semi-synthetic derivatives.…”

“…Betulonic acid diethylentriamine conjugate showed partial activity against methicillin-resistant S. aureus and the fungi C. neoformans [265]. Among triterpene-based polyamines, the most representative group is presented by triterpenic conjugates with linear and cyclic diamines 267-299 (Figure 11) [263][264][265]267,. The reactions involved both native acids and their semi-synthetic derivatives.…”

Messagenin–based Chalcones: Synthesis, Modification and Perspectives of Antidiabetic Potency

“…[8] A synthetic parthway to 29-nor-20-oxo-lupanes is also well-known by ozonolytic or RuO 4 oxidative approaches. [9,10] Chemical modifications of messagenin includes C3, C20, and C28 positions, for example, O-and N-aminopropylderivatives; [11] 20-(N'-acylhydrazinylidene)-derivatives, [12] etc. The library of platanic acid derivatives is more extended, for instance, a unique skeleton modification of several platanic carboxamides by an epimerization at C-19 and a condensation reaction to novel E-ring δ-lactams was reported recently.…”