Preparation of Imidodicarbonic diamide Derivatives by Microwave Method Using Layered Double Hydroxides (LDHs), as an Efficient Catalyst and Evaluation of their Anti-HIV Effect: Experimental and Theoretical Studies

Document Type : Original Article

Authors

1 Department of Organic Chemistry, Islamic Azad University Tehran North Branch, Tehran, Iran

2 Department of Medicinal Chemistry, School of Pharmacy, Zanjan University of Medical Sciences, Zanjan, Iran

3 Department of Medicinal Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran

4 Marine Pharmaceutical Science Research Center, Ahvaz Jundishapur University of Medical Sciences, Ahvaz, Iran

Abstract

In this paper, to develop green chemistry, a catalyst based on layered double hydroxides (LDHs) attached by hexamethylene-1,6-diisocyanate (HMDI) and citric acid (LDH-g-HMDI-citric acid) were prepared and characterized by FT-IR, XRD, EDX, SEM, TGA, and DTG analytical methods. The catalytic activity of this recyclable heterogeneous catalyst was evaluated for the synthesis of new imidodicarbonate diamide derivatives (biuret) under microwave conditions. The use of the microwave method led to the use of organic solvents in small amounts, reduced reaction times, and increased yields of products, which was achieved for the development of green chemistry and environmental protection. These biurets were evaluated for inhibitory activity on human immunodeficiency virus type 1 (HIV-1) by HIV-1 p24 antigen ELISA kit and three of them (5b, 5c, and 5f) had moderate activity on HIV -1 virus with IC50 values in the range of 55.1 to 100 μM compared to azidothymidine as the reference drug (IC50 = 0.11 μM). Finally, to investigate the mechanism of the effect of biuret compounds on the virus protease enzyme, docking analysis studies were performed and the results of in vitro test and docking study were in good correlation.

Keywords

Main Subjects

This is an open access article under the CC-BY-SA 4.0 license.( https://creativecommons.org/licenses/by-sa/4.0/)

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Applied Chemistry Today
Volume 18, Issue 68
September 2023
Pages 199-216

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