Trithiazacrown Ethers Containing Piperidine Heterocycle: Synthesis, Structural Characterization and Evaluation Of α‐Glucosidase Inhibitory Activity

Trithiazacrown Ethers Containing Piperidine Heterocycle: Synthesis, Structural Characterization and Evaluation Of α‐Glucosidase Inhibitory Activity Full article

Journal

ChemistrySelect
ISSN: 2365-6549

Output data

Year: 2024, Volume: 9, Number: 3, Article number : e202303741, Pages count : DOI: 10.1002/slct.202303741

Authors

Dat Nguyen Tien ¹ , Van Tran Thi Thanh ¹ , Nhung Dao Thi ¹ , Anh Cao Quoc ¹ , Hang Tran Thanh ¹ , Thao Vu Thi ² , Khrustalev Victor ^3,4 , Anh Le Tuan ¹

Affiliations

1	Faculty of Chemistry, VNU University of Science, Vietnam National University, Hanoi, 334 Nguyen Trai Street, Thanh Xuan, Ha Noi, 100000 Vietnam
2	Faculty of Engineering Physics and Nanotechnology, VNU University of Engineering and Technology, 144 Xuan Thuy, Cau Giay, Hanoi, Vietnam
3	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation
4	Peoples Friendship University of Russia (RUDN University), 117198 Moscow, Russian Federation

New derivatives of crown compounds were successfully prepared via multicomponent reactions of a thia-podand, an β-keto ester and ammonium acetate based on modifications of the Petrenko-Kritschenko reaction. The structure of the synthesized compounds was identified by physical-chemical methods of analysis including IR, NMR, HRMS, and single-crystal X-ray diffraction. In addition, an in vitro assay against the α-glucosidase of synthetic compounds was first evaluated and showed positive results. The most active compound exhibited an IC50 value of 5.69±0.27 μM, which is 37 fold more potent than the standard drug of acarbose (IC50 208.42±4.68 μM). Furthermore, prediction of ADMET parameters revealed that almost all synthesized trithiacrown ether derivatives expressed drug-like characteristics. Our results provide useful evidence that crown ether compounds are not only good chelators with metal ions but also scaffolds for developing lead candidates in the treatment of diabetic disease.

Dat N.T. , Van T.T.T. , Nhung D.T. , Anh C.Q. , Hang T.T. , Thao V.T. , Khrustalev V. , Anh L.T.
Trithiazacrown Ethers Containing Piperidine Heterocycle: Synthesis, Structural Characterization and Evaluation Of α‐Glucosidase Inhibitory Activity
ChemistrySelect. 2024. V.9. N3. e202303741 . DOI: 10.1002/slct.202303741 WOS Scopus OpenAlex

Web of science:	WOS:001143502800001
Scopus:	2-s2.0-85182481752
OpenAlex:	W4390914414

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