Design, Synthesis and in Vitro Α-Glucosidase Inhibition of Novel Coumarin-Pyridines As Potent Antidiabetic Agents

Design, Synthesis and in Vitro Α-Glucosidase Inhibition of Novel Coumarin-Pyridines As Potent Antidiabetic Agents Publisher

Adib M¹ ; Peytam F¹ ; Rahmanianjazi M¹ ; Mohammadikhanaposhtani M² ; Mahernia S^{3, 4} ; Bijanzadeh HR⁵ ; Jahani M¹ ; Imanparast S⁶ ; Faramarzi MA⁶ ; Mahdavi M⁷ ; Larijani B⁷

Show Affiliations

1. School of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran
2. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran
3. Department of Medicinal Chemistry, Drug Design and Development Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
4. Pharmaceutical Sciences Research Center, Institute of Pharmaceutical Sciences, Tehran University of Medical Sciences, Tehran, Iran
5. Environmental Science Department, Faculty of Natural Resources and Marine Sciences, Tarbiat Modares University, Tehran, Iran
6. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy and Biotechnology Research Center, Tehran University of Medical Sciences, Tehran, Iran
7. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran

Source: New Journal of Chemistry Published:2018

Abstract

In this work, we report an efficient, one-pot and three-component synthesis of novel coumarin fused pyridine derivatives 4a-p. Heating the mixture of 4-hydroxycoumarins and ammonium acetate in DMF gave the corresponding 4-aminocoumarins, which subsequently went through Michael addition-cyclocondensation with α-azidochalcone derivatives to produce our desired products in high yields. The synthesized compounds 4a-p were evaluated for α-glucosidase inhibitory activity and all of them exhibited excellent in vitro yeast α-glucosidase inhibition with IC50 values ranging from 101.0 ± 2.0 to 227.3 ± 1.4 μM when compared with the standard drug acarbose (IC50 = 750.0 ± 1.5 μM). A kinetic study of the most potent compound 4i revealed that it inhibited α-glucosidase in a competitive mode. A docking study of the most active compounds 4i, 4h, and 4j was also performed. © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

Style	Citing Format
MLA	Adib M, et al.. "Design, Synthesis and in Vitro Α-Glucosidase Inhibition of Novel Coumarin-Pyridines As Potent Antidiabetic Agents." New Journal of Chemistry, vol. 42, no. 21, 2018, pp. 17268-17278.
APA	Adib M, Peytam F, Rahmanianjazi M, Mohammadikhanaposhtani M, Mahernia S, Bijanzadeh HR, Jahani M, Imanparast S, Faramarzi MA, Mahdavi M, Larijani B (2018). Design, Synthesis and in Vitro Α-Glucosidase Inhibition of Novel Coumarin-Pyridines As Potent Antidiabetic Agents. New Journal of Chemistry, 42(21), 17268-17278.
Chicago	Adib M, Peytam F, Rahmanianjazi M, Mohammadikhanaposhtani M, Mahernia S, Bijanzadeh HR, Jahani M, et al.. "Design, Synthesis and in Vitro Α-Glucosidase Inhibition of Novel Coumarin-Pyridines As Potent Antidiabetic Agents." New Journal of Chemistry 42, no. 21 (2018): 17268-17278.
Harvard	Adib M et al. (2018) 'Design, Synthesis and in Vitro Α-Glucosidase Inhibition of Novel Coumarin-Pyridines As Potent Antidiabetic Agents', New Journal of Chemistry, 42(21), pp. 17268-17278.
Vancouver	Adib M, Peytam F, Rahmanianjazi M, Mohammadikhanaposhtani M, Mahernia S, Bijanzadeh HR, et al.. Design, Synthesis and in Vitro Α-Glucosidase Inhibition of Novel Coumarin-Pyridines As Potent Antidiabetic Agents. New Journal of Chemistry. 2018;42(21):17268-17278.
BibTex	@article{ author = {Adib M and Peytam F and Rahmanianjazi M and Mohammadikhanaposhtani M and Mahernia S and Bijanzadeh HR and Jahani M and Imanparast S and Faramarzi MA and Mahdavi M and Larijani B}, title = {Design, Synthesis and in Vitro Α-Glucosidase Inhibition of Novel Coumarin-Pyridines As Potent Antidiabetic Agents}, journal = {New Journal of Chemistry}, volume = {42}, number = {21}, pages = {17268-17278}, year = {2018} }
RIS	TY - JOUR AU - Adib M AU - Peytam F AU - Rahmanianjazi M AU - Mohammadikhanaposhtani M AU - Mahernia S AU - Bijanzadeh HR AU - Jahani M AU - Imanparast S AU - Faramarzi MA AU - Mahdavi M AU - Larijani B TI - Design, Synthesis and in Vitro Α-Glucosidase Inhibition of Novel Coumarin-Pyridines As Potent Antidiabetic Agents JO - New Journal of Chemistry VL - 42 IS - 21 SP - 17268 EP - 17278 PY - 2018 ER -

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