Synthesis of chalcone derivatives as potential anti-diabetic agents

Structure–activity relationship: chalcones derivatives with hydroxy (2b), chloro (4a), bromo (5b) and iodo (6a, 6b and 6c) substitutions at position 2 on A-ring and compounds (6e and 6g) with iodo substitution at position 3 on A-ring also showed the effect of enhance glucose uptake in 3T3-L1 adipocy...

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Published in:Bioorganic & medicinal chemistry letters 2012-06, Vol.22 (12), p.3912-3915
Main Authors: Hsieh, Chi-Ting, Hsieh, Tusty-Jiuan, El-Shazly, Mohamed, Chuang, Da-Wei, Tsai, Yi-Hong, Yen, Chiao-Ting, Wu, Shou-Fang, Wu, Yang-Chang, Chang, Fang-Rong
Format: Article
Language:English
Subjects:
3T3-L1 Cells
Adipocyte
Adipocytes - cytology
Adipocytes - drug effects
Adipocytes - metabolism
Aldol condensation
Animals
Biological and medical sciences
Biological Transport, Active - drug effects
Chalcone
Chalcones - chemical synthesis
Chalcones - pharmacology
Diabetes
Diabetes Mellitus - drug therapy
glucose
Glucose - agonists
Glucose - metabolism
Humans
hypoglycemic agents
Hypoglycemic Agents - chemical synthesis
Hypoglycemic Agents - pharmacology
Medical sciences
Mice
Pharmacology. Drug treatments
Structure-Activity Relationship
structure-activity relationships
Thiazolidinediones - pharmacology
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Summary:Structure–activity relationship: chalcones derivatives with hydroxy (2b), chloro (4a), bromo (5b) and iodo (6a, 6b and 6c) substitutions at position 2 on A-ring and compounds (6e and 6g) with iodo substitution at position 3 on A-ring also showed the effect of enhance glucose uptake in 3T3-L1 adipocytes. Chalcones bearing electron donating or electron withdrawing substitutions were prepared and their glucose uptake activity was evaluated. Chalcone derivatives were synthesized in one step protocol with high purity and yield. Chalcones with chloro, bromo, iodo and hydroxy substitutions at position 2 on A-ring exhibited the highest activity with glucose medium concentration (210 to 236mg/dl) compared to pioglitazone and rosiglitazone (230 and 263mg/dl, respectively). Also chalcones with iodo substitution at position 3 on A-ring were comparably active (⩽238mg/dl). The structure–activity relationship of the tested chalcones was studied and the findings were supported statistically
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2012.04.108