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

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. Messag...

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Published in:Asian journal of organic chemistry 2024-06, Vol.13 (6), p.n/a
Main Authors: Galimova, Zarema, Khusnutdinova, Elmira, Smirnova, Irina, Poptsov, Alexander, Spirikhin, Leonid, Gabdrakhmanova, Svetlana, Makara, Nina, Nguyen Thi Thu, Ha, Thi Tu Anh, Le, Thanh Tra, Nguyen, Thi Cham, Ba, Kazakova, Oxana
Format: Article
Language:English
Subjects:
betulin
chalcone derivatives
Claisen–Schmidt condensation
Glucosidase
messagenin
STZ-induced T1DM
α-glucosidase
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Summary: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
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202400072