Pantoprazole Derivatives: Synthesis, Urease Inhibition Assay and in Silico Molecular Modeling Studies

Pantoprazole Derivatives: Synthesis, Urease Inhibition Assay and in Silico Molecular Modeling Studies Publisher

Azizian H¹ ; Esmailnejad A² ; Fathi Vavsari V² ; Mahernia S³ ; Amanlou M³ ; Balalaie S^{2, 4}

Show Affiliations

1. Department of Medicinal Chemistry, School of Pharmacy, International Campus, Iran University of Medical Sciences, Tehran, Iran
2. Peptide Chemistry Research Center, K. N. Toosi University of Technology, P.O. Box, Tehran, 15875-4416, Iran
3. Drug Design and Development Research Center, The Institute of Pharmaceutical Sciences (TIPS), Tehran University of Medical Sciences, Tehran, Iran
4. Medical Biology Research Center, Kermanshah University of Medical Sciences, Kermanshah, Iran

Source: ChemistrySelect Published:2020

Abstract

A number of pantoprazole derivatives were synthesized and screened for their urease inhibitory properties. Some of them showed potent inhibitions against jack bean urease. All compounds showed varying degree of IC50 in the range of 25.85 to 181 μMol as compared to standard acetohydroxamic acid (AHA) (100±2.02 μMol). Derivatives bearing 5-aryl-1,3,4-oxadiazole ring substitutions (aryl= pyrazyl, pyridyl and phenyl) were found to be more potent inhibitors than AHA and pantoprazole. The most promising compound, 2-((3,4-dimethoxypyridin-2-yl)methylthio)-5-(pyrazin-2-yl)-1,3,4-oxadiazole 12, with IC50 value of 25.85±1.21 showed remarkable urease inhibition activity. In silico molecular modeling investigation performed to rationalize the possible binding interaction and ADME properties of compounds over the active site of urease enzyme. The induced fit docking study showed that compound 12 interacted with conserved residues His593 and Arg609 located at the mouth of the urease active site flap and are essential for enzyme catalytic activity. These target compounds could be further studied as a lead skeleton for discovery of novel urease inhibitors. © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Style	Citing Format
MLA	Azizian H, et al.. "Pantoprazole Derivatives: Synthesis, Urease Inhibition Assay and in Silico Molecular Modeling Studies." ChemistrySelect, vol. 5, no. 15, 2020, pp. 4580-4587.
APA	Azizian H, Esmailnejad A, Fathi Vavsari V, Mahernia S, Amanlou M, Balalaie S (2020). Pantoprazole Derivatives: Synthesis, Urease Inhibition Assay and in Silico Molecular Modeling Studies. ChemistrySelect, 5(15), 4580-4587.
Chicago	Azizian H, Esmailnejad A, Fathi Vavsari V, Mahernia S, Amanlou M, Balalaie S. "Pantoprazole Derivatives: Synthesis, Urease Inhibition Assay and in Silico Molecular Modeling Studies." ChemistrySelect 5, no. 15 (2020): 4580-4587.
Harvard	Azizian H et al. (2020) 'Pantoprazole Derivatives: Synthesis, Urease Inhibition Assay and in Silico Molecular Modeling Studies', ChemistrySelect, 5(15), pp. 4580-4587.
Vancouver	Azizian H, Esmailnejad A, Fathi Vavsari V, Mahernia S, Amanlou M, Balalaie S. Pantoprazole Derivatives: Synthesis, Urease Inhibition Assay and in Silico Molecular Modeling Studies. ChemistrySelect. 2020;5(15):4580-4587.
BibTex	@article{ author = {Azizian H and Esmailnejad A and Fathi Vavsari V and Mahernia S and Amanlou M and Balalaie S}, title = {Pantoprazole Derivatives: Synthesis, Urease Inhibition Assay and in Silico Molecular Modeling Studies}, journal = {ChemistrySelect}, volume = {5}, number = {15}, pages = {4580-4587}, year = {2020} }
RIS	TY - JOUR AU - Azizian H AU - Esmailnejad A AU - Fathi Vavsari V AU - Mahernia S AU - Amanlou M AU - Balalaie S TI - Pantoprazole Derivatives: Synthesis, Urease Inhibition Assay and in Silico Molecular Modeling Studies JO - ChemistrySelect VL - 5 IS - 15 SP - 4580 EP - 4587 PY - 2020 ER -

Science Communicator Platform

Authors

Authors Affiliations

Abstract