1. Synthesis and evaluation of ent-Conduramine C-1 derivatives as α-glucosidase inhibitors via CSI-mediated amination reaction.
- Author
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Park GM, Kong SJ, Park JH, Kang JE, An SH, Kim HS, Kim IS, Boggu PR, and Jung YH
- Subjects
- Molecular Structure, Amination, alpha-Glucosidases, Structure-Activity Relationship, Molecular Docking Simulation, Glycoside Hydrolase Inhibitors pharmacology, Isocyanates
- Abstract
Concise synthesis of ent-conduramine C-1 and its derivatives has been achieved by using commercially available d-ribose. The key steps in the synthesis are regioselective and diastereoselective amination of polybenzyl ethers by chlorosulfonyl isocyanate (CSI), chelation-controlled carbonyl addition, and intramolecular olefin metathesis. All of the synthesized compounds were evaluated for inhibitory activity against α-glucosidase. The derivatives 18 (IC
50 = 0.65 ± 0.03 mM) and 19 (IC50 = 0.26 ± 0.01 mM) were identified to be more potent than well-known α-glucosidase inhibitor acarbose (IC50 = 1.05 ± 0.17 mM) as a positive control., Competing Interests: Declaration of competing interest The authors declare the following financial interests/personal relationships which may be considered as potential competing interests: Young Hoon Jung reports financial support was provided by National Research Foundation of Korea (NRF) (No. 2020R1F1A1070288)., (Copyright © 2023 Elsevier Ltd. All rights reserved.)- Published
- 2023
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