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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.
Filho, Eclair Venturini; Pina, Jorge W S; Antoniazi, Mariana K; Loureiro, Laiza B; Ribeiro, Marcos A; Pinheiro, Carlos B; Guimarães, Celina J; de Oliveira, Fátima C E; Pessoa, Claudia; Taranto, Alex G; Greco, Sandro J.
Afiliação
  • Filho EV; Chemistry Department, Federal University of Espírito Santo, Vitória, Espírito Santo CEP.:29075-910, Brazil.
  • Pina JWS; Chemistry Department, Federal University of Espírito Santo, Vitória, Espírito Santo CEP.:29075-910, Brazil.
  • Antoniazi MK; Chemistry Department, Federal University of Espírito Santo, Vitória, Espírito Santo CEP.:29075-910, Brazil.
  • Loureiro LB; Chemistry Department, Federal University of Espírito Santo, Vitória, Espírito Santo CEP.:29075-910, Brazil.
  • Ribeiro MA; Chemistry Department, Federal University of Espírito Santo, Vitória, Espírito Santo CEP.:29075-910, Brazil.
  • Pinheiro CB; Physical Department, Minas Gerais Federal University, Av. Antônio Carlos 6627, Pampulha, Belo Horizonte, Minas Gerais CEP.: 30161-970 Brazil.
  • Guimarães CJ; Department of Physiology and Pharmacology, Faculty of Medicine, Federal University of Ceará., Fortaleza, Ceará CEP 60430-275, Brazil; Pharmacy Sector, Foundation of Oncology Control of the State of Amazonas, Manaus, Amazonas, CEP 69040-010, Brazil.
  • de Oliveira FCE; Department of Physiology and Pharmacology, Faculty of Medicine, Federal University of Ceará., Fortaleza, Ceará CEP 60430-275, Brazil.
  • Pessoa C; Department of Physiology and Pharmacology, Faculty of Medicine, Federal University of Ceará., Fortaleza, Ceará CEP 60430-275, Brazil.
  • Taranto AG; Laboratory of Drug Design and Bioinformatics, Federal University of São João del-Rei, São João del-Rei, Minas Gerais CEP: 36307-352, Brazil.
  • Greco SJ; Chemistry Department, Federal University of Espírito Santo, Vitória, Espírito Santo CEP.:29075-910, Brazil. Electronic address: sandro.greco@ufes.br.
Bioorg Med Chem Lett ; 48: 128240, 2021 09 15.
Article em En | MEDLINE | ID: mdl-34217828
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.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Pirazóis / Pirimidinas / Compostos Ferrosos / Simulação de Acoplamento Molecular / Aprendizado de Máquina / Metalocenos / Micro-Ondas / Antineoplásicos Limite: Humans Idioma: En Revista: Bioorg Med Chem Lett Assunto da revista: BIOQUIMICA / QUIMICA Ano de publicação: 2021 Tipo de documento: Article País de afiliação: Brasil País de publicação: Reino Unido
Texto completo
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Pirazóis / Pirimidinas / Compostos Ferrosos / Simulação de Acoplamento Molecular / Aprendizado de Máquina / Metalocenos / Micro-Ondas / Antineoplásicos Limite: Humans Idioma: En Revista: Bioorg Med Chem Lett Assunto da revista: BIOQUIMICA / QUIMICA Ano de publicação: 2021 Tipo de documento: Article País de afiliação: Brasil País de publicação: Reino Unido