Design, Synthesis, and Α-Glucosidase-Inhibitory Activity of Phenoxy-Biscoumarin

Design, Synthesis, and Α-Glucosidase-Inhibitory Activity of Phenoxy-Biscoumarin–N-Phenylacetamide Hybrids Publisher Pubmed

Ansari S¹ ; Azizian H² ; Pedrood K³ ; Yavari A³ ; Mojtabavi S⁴ ; Faramarzi MA⁴ ; Golshani S⁴ ; Hosseini S⁵ ; Biglar M³ ; Larijani B³ ; Rastegar H⁶ ; Hamedifar H¹ ; Mohammadikhanaposhtani M⁷ ; Mahdavi M³

Show Affiliations

1. CinnaGen Medical Biotechnology Research Center, Alborz University of Medical Sciences, Karaj, Iran
2. Department of Medicinal Chemistry, School of Pharmacy, Iran University of Medical Sciences, Tehran, Iran
3. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
4. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
5. Shahid Beheshti University of Medical Sciences, Tehran, Iran
6. Cosmetic Products Research Center, Iranian Food and Drug Administration, MOHE, Tehran, Iran
7. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran

Source: Archiv der Pharmazie Published:2021

Abstract

Thirteen new phenoxy-biscoumarin–N-phenylacetamide derivatives (7a–m) were designed based on a molecular hybridization approach as new α-glucosidase inhibitors. These compounds were synthesized with high yields and evaluated in vitro for their inhibitory activity against yeast α-glucosidase. The obtained results revealed that a significant proportion of the synthesized compounds showed considerable α-glucosidase-inhibitory activity in comparison to acarbose as a positive control. Representatively, 2-(4-(bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl)phenoxy)-N-(4-bromophenyl)acetamide (7f), with IC50 = 41.73 ± 0.38 µM against α-glucosidase, was around 18 times more potent than acarbose (IC50 = 750.0 ± 10.0 µM). This compound was a competitive α-glucosidase inhibitor. Molecular modeling and dynamic simulation of these compounds confirmed the obtained results through in vitro experiments. Prediction of the druglikeness/ADME/toxicity of the compound 7f and comparison with the standard drug acarbose showed that the new compound 7f was probably better than the standard drug in terms of toxicity. © 2021 Deutsche Pharmazeutische Gesellschaft

Style	Citing Format
MLA	Ansari S, et al.. "Design, Synthesis, and Α-Glucosidase-Inhibitory Activity of Phenoxy-Biscoumarin–N-Phenylacetamide Hybrids." Archiv der Pharmazie, vol. 354, no. 12, 2021, pp. -.
APA	Ansari S, Azizian H, Pedrood K, Yavari A, Mojtabavi S, Faramarzi MA, Golshani S, Hosseini S, Biglar M, Larijani B, Rastegar H, Hamedifar H, Mohammadikhanaposhtani M, Mahdavi M (2021). Design, Synthesis, and Α-Glucosidase-Inhibitory Activity of Phenoxy-Biscoumarin–N-Phenylacetamide Hybrids. Archiv der Pharmazie, 354(12), -.
Chicago	Ansari S, Azizian H, Pedrood K, Yavari A, Mojtabavi S, Faramarzi MA, Golshani S, et al.. "Design, Synthesis, and Α-Glucosidase-Inhibitory Activity of Phenoxy-Biscoumarin–N-Phenylacetamide Hybrids." Archiv der Pharmazie 354, no. 12 (2021): -.
Harvard	Ansari S et al. (2021) 'Design, Synthesis, and Α-Glucosidase-Inhibitory Activity of Phenoxy-Biscoumarin–N-Phenylacetamide Hybrids', Archiv der Pharmazie, 354(12), pp. -.
Vancouver	Ansari S, Azizian H, Pedrood K, Yavari A, Mojtabavi S, Faramarzi MA, et al.. Design, Synthesis, and Α-Glucosidase-Inhibitory Activity of Phenoxy-Biscoumarin–N-Phenylacetamide Hybrids. Archiv der Pharmazie. 2021;354(12):-.
BibTex	@article{ author = {Ansari S and Azizian H and Pedrood K and Yavari A and Mojtabavi S and Faramarzi MA and Golshani S and Hosseini S and Biglar M and Larijani B and Rastegar H and Hamedifar H and Mohammadikhanaposhtani M and Mahdavi M}, title = {Design, Synthesis, and Α-Glucosidase-Inhibitory Activity of Phenoxy-Biscoumarin–N-Phenylacetamide Hybrids}, journal = {Archiv der Pharmazie}, volume = {354}, number = {12}, pages = {-}, year = {2021} }
RIS	TY - JOUR AU - Ansari S AU - Azizian H AU - Pedrood K AU - Yavari A AU - Mojtabavi S AU - Faramarzi MA AU - Golshani S AU - Hosseini S AU - Biglar M AU - Larijani B AU - Rastegar H AU - Hamedifar H AU - Mohammadikhanaposhtani M AU - Mahdavi M TI - Design, Synthesis, and Α-Glucosidase-Inhibitory Activity of Phenoxy-Biscoumarin–N-Phenylacetamide Hybrids JO - Archiv der Pharmazie VL - 354 IS - 12 SP - EP - PY - 2021 ER -

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