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Synthesis of Biuret Derivatives as Potential HIV ‐1 Protease Inhibitors Using ( LDHs‐g‐HMDI‐Citric Acid), as a Green Recyclable Catalyst
Author(s) -
Ghiasifar Zahra,
Salehabadi Hafezeh,
Adibpour Neda,
Alipour Eskandar,
Kobarfard Farzad,
Shoushizadeh Mohammad Reza
Publication year - 2021
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.12152
Subject(s) - citric acid , chemistry , biuret test , nuclear chemistry , catalysis , protease , isocyanate , urea , polymer chemistry , enzyme , biochemistry , organic chemistry , polyurethane
In this study, a novel catalyst based on layered double hydroxides (LDHs) attached by hexamethylene‐1,6‐diisocyanate (HMDI) and citric acid (LDHs‐g‐HMDI‐Citric acid) is reported and used to increase the yield of biurets synthesis. Biuret derivatives 5a – n were prepared by reaction of several phenyl allophanates ( 3a – d ), which prepared from the reaction of phenyl chloroformate and urea derivatives ( 2a – d ), with variously substituted amines ( 4a – g ) in the presence of LDHs‐g‐HMDI‐Citric acid as a reusable heterogeneous catalyst at reflux condition for 60–180 min. These biurets ( 5a – n ) were evaluated for human immunodeficiency virus type‐1 (HIV‐1) protease inhibitory activity by HIV‐1 p24 antigen ELISA kit and six of them (5n, 5i, 5j, 5 m, 5f, and 5a) showed moderate activity on HIV‐1 virus with IC 50 values ranging from 55 to 100 μM compared with the azidothymidine as the reference drug (IC 50 = 0.11 μM). Results of the in vitro test and docking study were in good correlation.