New Solid Phase Methodology for the Synthesis of Biscoumarin Derivatives: Experimental and in Silico Approaches

New Solid Phase Methodology for the Synthesis of Biscoumarin Derivatives: Experimental and in Silico Approaches Publisher

Zarenezhad E¹ ; Montazer MN² ; Tabatabaee M³ ; Irajie C⁴ ; Iraji A^{5, 6}

Show Affiliations

1. Noncommunicable Diseases Research Center, Fasa University of Medical Sciences, Fasa, Iran
2. Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
3. Department of Chemistry, Yazd Branch, Islamic Azad University, Yazd, Iran
4. Department of Medical Biotechnology, School of Advanced Medical Sciences and Technologies, Shiraz University of Medical Sciences, Shiraz, Iran
5. Stem Cells Technology Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
6. Central Research Laboratory, Shiraz University of Medical Sciences, Shiraz, Iran

Source: BMC Chemistry Published:2022

Abstract

The simple and greener one-pot approach for the synthesis of biscoumarin derivatives using catalytic amounts of nano-MoO3 catalyst under mortar-pestle grinding was described. The use of non-toxic and mild catalyst, cost-effectiveness, ordinary grinding, and good to the excellent yield of the final product makes this procedure a more attractive pathway for the synthesis of biologically remarkable pharmacophores. Accordingly, biscoumarin derivatives were successfully extended in the developed protocols. Next, a computational investigation was performed to identify the potential biological targets of this set of compounds. In this case, first, a similarity search on different virtual libraries was performed to find an ideal biological target for these derivatives. Results showed that the synthesized derivatives can be α-glucosidase inhibitors. In another step, molecular docking studies were carried out against human lysosomal acid-alpha-glucosidase (PDB ID: 5NN8) to determine the detailed binding modes and critical interactions with the proposed target. In silico assessments showed the gold score value in the range of 17.56 to 29.49. Additionally, molecular dynamic simulations and the MM-GBSA method of the most active derivative against α-glucosidase were conducted to study the behavior of selected compounds in the biological system. Ligand 1 stabilized after around 30 ns and participated in various interactions with Trp481, Asp518, Asp616, His674, Phe649, and Leu677 residues. © 2022, The Author(s).

Related Docs

View other Related Docs

1. Synthesis, in Vitro Α-Glucosidase Inhibitory Activities, and Molecular Dynamic Simulations of Novel 4-Hydroxyquinolinone-Hydrazones As Potential Antidiabetic Agents, Scientific Reports (2023)

2. Design, Synthesis, and in Silico Studies of Quinoline-Based-Benzo[D]Imidazole Bearing Different Acetamide Derivatives As Potent Α-Glucosidase Inhibitors, Scientific Reports (2022)

3. Design, Synthesis, and in Silico Studies of Benzimidazole Bearing Phenoxyacetamide Derivatives As Α-Glucosidase and Α-Amylase Inhibitors, Journal of Molecular Structure (2022)

4. Synthesis, in Vitro Inhibitor Screening, Structure–Activity Relationship, and Molecular Dynamic Simulation Studies of Novel Thioquinoline Derivatives As Potent Α-Glucosidase Inhibitors, Scientific Reports (2023)

5. Synthesis and Bioactivities Evaluation of Quinazolin-4(3H)-One Derivatives As Α-Glucosidase Inhibitors, BMC Chemistry (2022)

6. Evaluation of Novel 2-(Quinoline-2-Ylthio)Acetamide Derivatives Linked to Diphenyl-Imidazole As Α-Glucosidase Inhibitors: Insights From in Silico, in Vitro, and in Vivo Studies on Their Anti-Diabetic Properties, European Journal of Medicinal Chemistry (2024)

7. Design, Synthesis, and Molecular Docking Studies of Diphenylquinoxaline-6-Carbohydrazide Hybrids As Potent Α-Glucosidase Inhibitors, BMC Chemistry (2022)

8. Synthesis and Structure–Activity Relationship Studies of Benzimidazole-Thioquinoline Derivatives As Α-Glucosidase Inhibitors, Scientific Reports (2023)

Experts (# of related papers)

View all Related Experts

Somayeh Mojtabavi (12)

Mohammad Ali Faramarzi (12)

Style	Citing Format
MLA	Zarenezhad E, et al.. "New Solid Phase Methodology for the Synthesis of Biscoumarin Derivatives: Experimental and in Silico Approaches." BMC Chemistry, vol. 16, no. 1, 2022, pp. -.
APA	Zarenezhad E, Montazer MN, Tabatabaee M, Irajie C, Iraji A (2022). New Solid Phase Methodology for the Synthesis of Biscoumarin Derivatives: Experimental and in Silico Approaches. BMC Chemistry, 16(1), -.
Chicago	Zarenezhad E, Montazer MN, Tabatabaee M, Irajie C, Iraji A. "New Solid Phase Methodology for the Synthesis of Biscoumarin Derivatives: Experimental and in Silico Approaches." BMC Chemistry 16, no. 1 (2022): -.
Harvard	Zarenezhad E et al. (2022) 'New Solid Phase Methodology for the Synthesis of Biscoumarin Derivatives: Experimental and in Silico Approaches', BMC Chemistry, 16(1), pp. -.
Vancouver	Zarenezhad E, Montazer MN, Tabatabaee M, Irajie C, Iraji A. New Solid Phase Methodology for the Synthesis of Biscoumarin Derivatives: Experimental and in Silico Approaches. BMC Chemistry. 2022;16(1):-.
BibTex	@article{ author = {Zarenezhad E and Montazer MN and Tabatabaee M and Irajie C and Iraji A}, title = {New Solid Phase Methodology for the Synthesis of Biscoumarin Derivatives: Experimental and in Silico Approaches}, journal = {BMC Chemistry}, volume = {16}, number = {1}, pages = {-}, year = {2022} }
RIS	TY - JOUR AU - Zarenezhad E AU - Montazer MN AU - Tabatabaee M AU - Irajie C AU - Iraji A TI - New Solid Phase Methodology for the Synthesis of Biscoumarin Derivatives: Experimental and in Silico Approaches JO - BMC Chemistry VL - 16 IS - 1 SP - EP - PY - 2022 ER -

Science Communicator Platform

Authors

Authors Affiliations

Abstract