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BIBTEX RIS

Synthesis, docking, machine learning and antiproliferative activity of the 6-ferrocene/heterocycle-2-aminopyrimidine and 5-ferrocene-1H-Pyrazole derivatives obtained by microwave-assisted Atwal reaction as potential anticancer agents

2021; Elsevier BV; Volume: 48; Linguagem: Inglês

10.1016/j.bmcl.2021.128240

1464-3405

Éclair Venturini Filho, Jorge W.S. Pina, Mariana K. Antoniazi, Laiza B. Loureiro, Marcos A. Ribeiro, Carlos B. Pinheiro, Celina J. Guimarães, Fátima C.E. de Oliveira, Cláudia Pessoa, Alex Gutterres Taranto, Sandro J. Greco,

Synthesis and Biological Evaluation

A simple and fast methodology under microwave irradiation for the synthesis of 2-aminopyrimidine and pyrazole derivatives using Atwal reaction is reported. After the optimization of the reaction conditions, eight 2-aminolpyrimidines containing ferrocene and heterocycles and three ferrocene pyrazoles were synthesized from the respective chalcones in good yields. Eight compounds had their structure determined by X-ray diffraction. The molecular hybrid 6a-h and 9a-c were tested on four cancer cell lines - HCT116, PC3, HL60 and SNB19 - where four pyrimidine 6a, 6f-h and one pyrazole 9c derivatives show promising antiproliferative activity. In addition, docking simulation and machine learning methods were carried out to explain the biological activity achieved by the synthetized compounds.