Cytotoxic Activity of Piperazin-2-One-Based Structures: Cyclic Imines, Lactams, Aminophosphonates, and Their Derivatives

Abstract

N-Heterocycles are considered as desirable scaffolds for the development of novel lead compounds for anticancer drug research. Among them, phosphorus-containing amino-derivatives play a crucial role. A series of imines and products of their further reactions with P-nucleophiles were obtained starting from vicinal bisamines. Reaction of ethylenediamine and α-carbonyl esters yielded in novel unexpected products, which structures were confirmed by crystallographic measurements. The cytotoxic activity evaluation was done on a variety of cell lines including HUH7, AKH12, DAOY, UW228-2, D283, D425, and U251. Human umbilical vein endothelial cells (HUVECs) were used as control. Two of the tested compounds, bearing TADDOL-derived, and trifluoromethyl substituents showed a significant effect on cell viability, though comparable to nonmalignant cells.

Promiscuous Lipase-Catalyzed Markovnikov Addition of H-Phosphites to Vinyl Esters for the Synthesis of Cytotoxic α-Acyloxy Phosphonate Derivatives

“…α-Hydroxy phosphonate derivatives are of great importance due to their various biological actions and therapeutic applications such as bactericidal [ 5 ], fungicidal [ 6 ], antitumor [ 7 ], and HIV inhibitory activities [ 8 ]. The high interest in this class of compounds has been reflected in numerous publications on their synthesis, modification, and application not only in medical chemistry [ 9 , 10 , 11 , 12 , 13 , 14 ]. It was shown that further functionalization of the hydroxy group has a pivotal impact on the biological activity of the modified α-hydroxy phosphonates.…”

Relationship between Structure and Antibacterial Activity of α-Aminophosphonate Derivatives Obtained via Lipase-Catalyzed Kabachnik−Fields Reaction

“…α-Aminophosphonates appear to be a very important class of organic compounds because of their potential biological activities [ 1 , 2 , 3 , 4 ]. The distinctive character of bioactive organophosphorus compounds has established their wide applicability in agricultural and medicinal chemistry [ 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 ]. α-Aminophosphonates ( Figure 1 ) play a crucial role as a platform to design new drugs [ 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 ].…”

Antitumor Activity against A549 Cancer Cells of Three Novel Complexes Supported by Coating with Silver Nanoparticles

“…These compounds are at the center of interest due to their numerous pharmacological possibilities such as anticancer, antiviral, antimicrobial, antioxidant, and antineoplastic [ 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 ]. Coordination compounds containing such derivatives are considered to be a promising class of antineoplastic agent showing cytotoxic activity against different cell lines [ 13 , 14 , 15 , 16 ].…”