New Thiosemicarbazide-1,2,3-Triazole Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, and Biological Evaluation

New Thiosemicarbazide-1,2,3-Triazole Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, and Biological Evaluation Publisher

Bakherad Z^{1, 2} ; Mohammadikhanaposhtani M³ ; Sadeghialiabadi H¹ ; Rezaei S⁴ ; Fassihi A¹ ; Bakherad M⁵ ; Rastegar H² ; Biglar M⁶ ; Saghaie L¹ ; Larijani B⁶ ; Mahdavi M⁶

Show Affiliations

1. Department of Medicinal Chemistry, School of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences, 81746-73461, Isfahan, Iran
2. Food and Drug Research Institute, Food and Drug Administration, MOHE, Tehran, Iran
3. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran
4. School of Pharmacy, Tabriz University of Medical Sciences, Tabriz, Iran
5. School of Chemistry, Shahrood University of Technology, Shahrood, Iran
6. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran

Source: Journal of Molecular Structure Published:2019

Abstract

A new series of thiosemicarbazide-1,2,3-triazole hybrids 10a-o has been synthesized, characterized by 1H NMR, 13C NMR, and screened for their in vitro α-glucosidase inhibitory activity. All of the synthesized compounds displayed excellent α-glucosidase inhibitory activity with IC50 values in the range of 75.0 ± 0.5 to 253.0 ± 0.5 μM, as compared to the standard drug acarbose (IC50 = 750.0 ± 1.5 μM). Among the synthesized compounds, compound 10h (IC50 = 75.0 ± 0.5)with 4-methoxy group at phenyl part of thiosemicarbazide moiety and 2,6-dichloro substituents at benzyl moiety was found to be the most potent compound. Kinetic analysis revealed that compound 10h is a competitive inhibitor for α-glucosidase. Docking study of compound 10h in the active site of α-glucosidase showed that this compound interacted with residues His239, His279, Glu304, Gly306, and Arg312. © 2019 Elsevier B.V.

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Style	Citing Format
MLA	Bakherad Z, et al.. "New Thiosemicarbazide-1,2,3-Triazole Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, and Biological Evaluation." Journal of Molecular Structure, vol. 1192, no. , 2019, pp. 192-200.
APA	Bakherad Z, Mohammadikhanaposhtani M, Sadeghialiabadi H, Rezaei S, Fassihi A, Bakherad M, Rastegar H, Biglar M, Saghaie L, Larijani B, Mahdavi M (2019). New Thiosemicarbazide-1,2,3-Triazole Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, and Biological Evaluation. Journal of Molecular Structure, 1192(), 192-200.
Chicago	Bakherad Z, Mohammadikhanaposhtani M, Sadeghialiabadi H, Rezaei S, Fassihi A, Bakherad M, Rastegar H, et al.. "New Thiosemicarbazide-1,2,3-Triazole Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, and Biological Evaluation." Journal of Molecular Structure 1192, no. (2019): 192-200.
Harvard	Bakherad Z et al. (2019) 'New Thiosemicarbazide-1,2,3-Triazole Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, and Biological Evaluation', Journal of Molecular Structure, 1192(), pp. 192-200.
Vancouver	Bakherad Z, Mohammadikhanaposhtani M, Sadeghialiabadi H, Rezaei S, Fassihi A, Bakherad M, et al.. New Thiosemicarbazide-1,2,3-Triazole Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, and Biological Evaluation. Journal of Molecular Structure. 2019;1192():192-200.
BibTex	@article{ author = {Bakherad Z and Mohammadikhanaposhtani M and Sadeghialiabadi H and Rezaei S and Fassihi A and Bakherad M and Rastegar H and Biglar M and Saghaie L and Larijani B and Mahdavi M}, title = {New Thiosemicarbazide-1,2,3-Triazole Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, and Biological Evaluation}, journal = {Journal of Molecular Structure}, volume = {1192}, number = {}, pages = {192-200}, year = {2019} }
RIS	TY - JOUR AU - Bakherad Z AU - Mohammadikhanaposhtani M AU - Sadeghialiabadi H AU - Rezaei S AU - Fassihi A AU - Bakherad M AU - Rastegar H AU - Biglar M AU - Saghaie L AU - Larijani B AU - Mahdavi M TI - New Thiosemicarbazide-1,2,3-Triazole Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, and Biological Evaluation JO - Journal of Molecular Structure VL - 1192 IS - SP - 192 EP - 200 PY - 2019 ER -

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