(Phenylamino)pyrimidine-1,2,3-triazole derivatives as analogs of imatinib: searching for novel compounds against chronic myeloid leukemia

The enzyme tyrosine kinase BCR-Abl-1 is the main molecular target in the treatment of chronic myeloid leukemia and can be competitively inhibited by tyrosine kinase inhibitors such as imatinib. New potential competitive inhibitors were synthesized using the (phenylamino)pyrimidine-pyridine (PAPP) gr...

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Published in:	Beilstein journal of organic chemistry Vol. 17; no. 1; pp. 2260 - 2269
Main Authors:	Pimentel, Luiz Claudio Ferreira, Hoelz, Lucas Villas Boas, Canzian, Henayle Fernandes, Branco, Frederico Silva Castelo, de Oliveira, Andressa Paula, Campos, Vinicius Rangel, Júnior, Floriano Paes Silva, Dantas, Rafael Ferreira, Resende, Jackson Antônio Lamounier Camargos, Cunha, Anna Claudia, Boechat, Nubia, Bastos, Mônica Macedo
Format:	Journal Article
Language:	English
Published:	Germany Beilstein-Institut zur Föerderung der Chemischen Wissenschaften 01.09.2021 Beilstein-Institut
Subjects:	(phenylamino)pyrimidine-pyridine 1,2,3-triazole 1,3-dipolar cycloaddition BCR-ABL protein Binding sites Chemistry Chromosomes Chronic myeloid leukemia Confidence intervals Cytotoxicity Design Enzymes Full Research Paper Fusion protein Imatinib Kinases Leukemia Mutation Myeloid leukemia Protein-tyrosine kinase Triazoles (phenylamino)pyrimidine-pyridine chronic myeloid leukemia imatinib 1,2,3-triazole 1,3-dipolar cycloaddition
ISSN:	1860-5397, 2195-951X, 1860-5397
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Abstract	The enzyme tyrosine kinase BCR-Abl-1 is the main molecular target in the treatment of chronic myeloid leukemia and can be competitively inhibited by tyrosine kinase inhibitors such as imatinib. New potential competitive inhibitors were synthesized using the (phenylamino)pyrimidine-pyridine (PAPP) group as a pharmacophoric fragment, and these compounds were biologically evaluated. The synthesis of twelve new compounds was performed in three steps and assisted by microwave irradiation in a 1,3-dipolar cycloaddition to obtain 1,2,3-triazole derivatives substituted on carbon C-4 of the triazole nucleus. All compounds were evaluated for their inhibitory activities against a chronic myeloid leukemia cell line (K562) that expresses the enzyme tyrosine kinase BCR-Abl-1 and against healthy cells (WSS-1) to observe their selectivity. Three compounds showed promising results, with IC 50 values between 1.0 and 7.3 μM, and were subjected to molecular docking studies. The results suggest that such compounds can interact at the same binding site as imatinib, probably sharing a competitive inhibition mechanism. One compound showed the greatest interaction affinity for BCR-Abl-1 in the docking studies.
AbstractList	The enzyme tyrosine kinase BCR-Abl-1 is the main molecular target in the treatment of chronic myeloid leukemia and can be competitively inhibited by tyrosine kinase inhibitors such as imatinib. New potential competitive inhibitors were synthesized using the (phenylamino)pyrimidine-pyridine (PAPP) group as a pharmacophoric fragment, and these compounds were biologically evaluated. The synthesis of twelve new compounds was performed in three steps and assisted by microwave irradiation in a 1,3-dipolar cycloaddition to obtain 1,2,3-triazole derivatives substituted on carbon C-4 of the triazole nucleus. All compounds were evaluated for their inhibitory activities against a chronic myeloid leukemia cell line (K562) that expresses the enzyme tyrosine kinase BCR-Abl-1 and against healthy cells (WSS-1) to observe their selectivity. Three compounds showed promising results, with IC50 values between 1.0 and 7.3 μM, and were subjected to molecular docking studies. The results suggest that such compounds can interact at the same binding site as imatinib, probably sharing a competitive inhibition mechanism. One compound showed the greatest interaction affinity for BCR-Abl-1 in the docking studies. The enzyme tyrosine kinase BCR-Abl-1 is the main molecular target in the treatment of chronic myeloid leukemia and can be competitively inhibited by tyrosine kinase inhibitors such as imatinib. New potential competitive inhibitors were synthesized using the (phenylamino)pyrimidine-pyridine (PAPP) group as a pharmacophoric fragment, and these compounds were biologically evaluated. The synthesis of twelve new compounds was performed in three steps and assisted by microwave irradiation in a 1,3-dipolar cycloaddition to obtain 1,2,3-triazole derivatives substituted on carbon C-4 of the triazole nucleus. All compounds were evaluated for their inhibitory activities against a chronic myeloid leukemia cell line (K562) that expresses the enzyme tyrosine kinase BCR-Abl-1 and against healthy cells (WSS-1) to observe their selectivity. Three compounds showed promising results, with IC50 values between 1.0 and 7.3 μM, and were subjected to molecular docking studies. The results suggest that such compounds can interact at the same binding site as imatinib, probably sharing a competitive inhibition mechanism. One compound showed the greatest interaction affinity for BCR-Abl-1 in the docking studies.The enzyme tyrosine kinase BCR-Abl-1 is the main molecular target in the treatment of chronic myeloid leukemia and can be competitively inhibited by tyrosine kinase inhibitors such as imatinib. New potential competitive inhibitors were synthesized using the (phenylamino)pyrimidine-pyridine (PAPP) group as a pharmacophoric fragment, and these compounds were biologically evaluated. The synthesis of twelve new compounds was performed in three steps and assisted by microwave irradiation in a 1,3-dipolar cycloaddition to obtain 1,2,3-triazole derivatives substituted on carbon C-4 of the triazole nucleus. All compounds were evaluated for their inhibitory activities against a chronic myeloid leukemia cell line (K562) that expresses the enzyme tyrosine kinase BCR-Abl-1 and against healthy cells (WSS-1) to observe their selectivity. Three compounds showed promising results, with IC50 values between 1.0 and 7.3 μM, and were subjected to molecular docking studies. The results suggest that such compounds can interact at the same binding site as imatinib, probably sharing a competitive inhibition mechanism. One compound showed the greatest interaction affinity for BCR-Abl-1 in the docking studies. The enzyme tyrosine kinase BCR-Abl-1 is the main molecular target in the treatment of chronic myeloid leukemia and can be competitively inhibited by tyrosine kinase inhibitors such as imatinib. New potential competitive inhibitors were synthesized using the (phenylamino)pyrimidine-pyridine (PAPP) group as a pharmacophoric fragment, and these compounds were biologically evaluated. The synthesis of twelve new compounds was performed in three steps and assisted by microwave irradiation in a 1,3-dipolar cycloaddition to obtain 1,2,3-triazole derivatives substituted on carbon C-4 of the triazole nucleus. All compounds were evaluated for their inhibitory activities against a chronic myeloid leukemia cell line (K562) that expresses the enzyme tyrosine kinase BCR-Abl-1 and against healthy cells (WSS-1) to observe their selectivity. Three compounds showed promising results, with IC values between 1.0 and 7.3 μM, and were subjected to molecular docking studies. The results suggest that such compounds can interact at the same binding site as imatinib, probably sharing a competitive inhibition mechanism. One compound showed the greatest interaction affinity for BCR-Abl-1 in the docking studies. The enzyme tyrosine kinase BCR-Abl-1 is the main molecular target in the treatment of chronic myeloid leukemia and can be competitively inhibited by tyrosine kinase inhibitors such as imatinib. New potential competitive inhibitors were synthesized using the (phenylamino)pyrimidine-pyridine (PAPP) group as a pharmacophoric fragment, and these compounds were biologically evaluated. The synthesis of twelve new compounds was performed in three steps and assisted by microwave irradiation in a 1,3-dipolar cycloaddition to obtain 1,2,3-triazole derivatives substituted on carbon C-4 of the triazole nucleus. All compounds were evaluated for their inhibitory activities against a chronic myeloid leukemia cell line (K562) that expresses the enzyme tyrosine kinase BCR-Abl-1 and against healthy cells (WSS-1) to observe their selectivity. Three compounds showed promising results, with IC 50 values between 1.0 and 7.3 μM, and were subjected to molecular docking studies. The results suggest that such compounds can interact at the same binding site as imatinib, probably sharing a competitive inhibition mechanism. One compound showed the greatest interaction affinity for BCR-Abl-1 in the docking studies.
Author	Pimentel, Luiz Claudio Ferreira Campos, Vinicius Rangel Dantas, Rafael Ferreira Canzian, Henayle Fernandes Bastos, Mônica Macedo de Oliveira, Andressa Paula Branco, Frederico Silva Castelo Júnior, Floriano Paes Silva Cunha, Anna Claudia Hoelz, Lucas Villas Boas Resende, Jackson Antônio Lamounier Camargos Boechat, Nubia
AuthorAffiliation	3 Laboratório de Bioquímica Experimental e Computacional de Farmacos, Fundaçao Oswaldo Cruz, Instituto Oswaldo Cruz, CEP 21040-900, Rio de Janeiro, Brazil 1 Laboratorio de Sintese de Farmacos – LASFAR, Fundacao Oswaldo Cruz, Instituto de Tecnologia em Farmacos, Farmanguinhos –Manguinhos, CEP 21041-250, Rio de Janeiro, Brazil 2 Departamento de Química Orgânica, Universidade Federal Fluminense, Campus do Valonguinho, CEP 24020-150,Niterói, Brazil 4 Instituto de Ciências Exatas e da Terra, Universidade Federal de Mato Grosso, Campus Universitário do Araguaia, CEP 78698-000, Pontal do Araguaia, MT, Brazil
AuthorAffiliation_xml	– name: 3 Laboratório de Bioquímica Experimental e Computacional de Farmacos, Fundaçao Oswaldo Cruz, Instituto Oswaldo Cruz, CEP 21040-900, Rio de Janeiro, Brazil – name: 1 Laboratorio de Sintese de Farmacos – LASFAR, Fundacao Oswaldo Cruz, Instituto de Tecnologia em Farmacos, Farmanguinhos –Manguinhos, CEP 21041-250, Rio de Janeiro, Brazil – name: 4 Instituto de Ciências Exatas e da Terra, Universidade Federal de Mato Grosso, Campus Universitário do Araguaia, CEP 78698-000, Pontal do Araguaia, MT, Brazil – name: 2 Departamento de Química Orgânica, Universidade Federal Fluminense, Campus do Valonguinho, CEP 24020-150,Niterói, Brazil
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Copyright	Copyright © 2021, Pimentel et al. Copyright © 2021, Pimentel et al. This work is published under https://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License. Copyright © 2021, Pimentel et al. 2021 Pimentel et al.
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Snippet	The enzyme tyrosine kinase BCR-Abl-1 is the main molecular target in the treatment of chronic myeloid leukemia and can be competitively inhibited by tyrosine...
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SubjectTerms	(phenylamino)pyrimidine-pyridine 1,2,3-triazole 1,3-dipolar cycloaddition BCR-ABL protein Binding sites Chemistry Chromosomes Chronic myeloid leukemia Confidence intervals Cytotoxicity Design Enzymes Full Research Paper Fusion protein Imatinib Kinases Leukemia Mutation Myeloid leukemia Protein-tyrosine kinase Triazoles
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Title	(Phenylamino)pyrimidine-1,2,3-triazole derivatives as analogs of imatinib: searching for novel compounds against chronic myeloid leukemia
URI	https://www.ncbi.nlm.nih.gov/pubmed/34621389 https://www.proquest.com/docview/2595280028 https://www.proquest.com/docview/2580690603 https://pubmed.ncbi.nlm.nih.gov/PMC8450943 https://doaj.org/article/52c4d12e69cd40e2bc4c1ffb5eeb6e3c
Volume	17
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