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- Title
3-(((1 S ,3 S)-3-((R)-Hydroxy(4-(trifluoromethyl)phenyl)methyl)-4-oxocyclohexyl)methyl)pentane-2,4-dione: Design and Synthesis of New Stereopure Multi-Target Antidiabetic Agent.
- Authors
Sadiq, Abdul; Mahnashi, Mater H.; Rashid, Umer; Jan, Muhammad Saeed; Alshahrani, Mohammed Abdulrahman; Huneif, Mohammed A.
- Abstract
The chiral drug candidates have more effective binding affinities for their specific protein or receptor site for the onset of pharmacological action. Achieving all carbon stereopure compounds is not trivial in chemical synthesis. However, with the development of asymmetric organocatalysis, the synthesis of certain vital chiral drug candidates is now possible. In this research, we have synthesized 3-(((1S,3S)-3-((R)-hydroxy(4-(trifluoromethyl)phenyl)methyl)-4-oxocyclohexyl)methyl)pentane-2,4-dione (S,S,R-5) and have evaluated it potential as multi-target antidiabetic agent. The stereopure compound S,S,R-5 was synthesized with a 99:1 enantiomeric ratio. The synthesized compound gave encouraging results against all in vitro antidiabetic targets, exhibiting IC50 values of 6.28, 4.58, 0.91, and 2.36 in α-glucosidase, α-amylase, PTP1B, and DPPH targets, respectively. The molecular docking shows the binding of the compound in homology models of the respective enzymes. In conclusion, we have synthesized a new chiral molecule (S,S,R-5). The compound proved to be a potential inhibitor of the tested antidiabetic targets. With the observed results and molecular docking, it is evident that S,S,R-5 is a potential multitarget antidiabetic agent. Our study laid the baseline for the animal-based studies of this compound in antidiabetic confirmation.
- Subjects
ORGANOCATALYSIS; HYPOGLYCEMIC agents; CHIRAL drugs; MOLECULAR docking; PROTEIN receptors; CHEMICAL synthesis; ALPHA-glucosidases
- Publication
Molecules, 2022, Vol 27, Issue 10, p3265
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules27103265