First Synthesis of Betulin 20-Acylhydrazones

Myasoedova, Yu. V.; Belyaeva, E. R.; Garifullina, L. R.; Prosvirnina, D. A.; Ishmuratov, G. Yu.

doi:10.1134/s1070428022010109

Cited by 3 publications

(1 citation statement)

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“…[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.…”

Section: Introductionmentioning

confidence: 99%

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

Galimova,

Khusnutdinova,

Smirnova

et al. 2024

Asian J Org Chem

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A series of messagenin‐based chalcones has been synthesized by Claisen‐Schmidt condensation and screened for in vitro α‐glucosidase inhibitory activity. The heterocyclization of 30‐(3‐pyridinylidene)‐messagenin led to syn/anti N‐acetyl‐pyrazoles in a ratio of 2:1 that were isolated by HPLC. Messagenin chalcones act as α‐glucosidase inhibitors with IC50 range from 0.055 to 80.70 µM. The lead nanomolar level α‐glucosidase inhibitor 30‐(4‐hydroxymethyl‐benzylidene)‐messagenin 10 was studied for antihyperglycemic activity on streptozotocin‐induced diabetic animal models using in vivo mechanism‐based assays. In a rat model of STZ‐induced T1DM, compound 10 (20 mg/kg, orally) exhibited antihyperlipidemic activity, reducing AIP (p>0.05) and CRI (p<0.05) compared to control. Compound 10 improved diabetic nephropathy, locomotor activity in rats, and reduced diabetes‐related mortality.

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