(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...

Full description

Saved in:

Bibliographic Details
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
Online Access:	Get full text
Tags:	Add Tag No Tags, Be the first to tag this record!

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
Author_xml	– sequence: 1 givenname: Luiz Claudio Ferreira orcidid: 0000-0001-7850-3888 surname: Pimentel fullname: Pimentel, Luiz Claudio Ferreira – sequence: 2 givenname: Lucas Villas Boas surname: Hoelz fullname: Hoelz, Lucas Villas Boas – sequence: 3 givenname: Henayle Fernandes surname: Canzian fullname: Canzian, Henayle Fernandes – sequence: 4 givenname: Frederico Silva Castelo orcidid: 0000-0002-0863-7087 surname: Branco fullname: Branco, Frederico Silva Castelo – sequence: 5 givenname: Andressa Paula surname: de Oliveira fullname: de Oliveira, Andressa Paula – sequence: 6 givenname: Vinicius Rangel orcidid: 0000-0003-3676-5964 surname: Campos fullname: Campos, Vinicius Rangel – sequence: 7 givenname: Floriano Paes Silva surname: Júnior fullname: Júnior, Floriano Paes Silva – sequence: 8 givenname: Rafael Ferreira surname: Dantas fullname: Dantas, Rafael Ferreira – sequence: 9 givenname: Jackson Antônio Lamounier Camargos surname: Resende fullname: Resende, Jackson Antônio Lamounier Camargos – sequence: 10 givenname: Anna Claudia orcidid: 0000-0002-1336-5928 surname: Cunha fullname: Cunha, Anna Claudia – sequence: 11 givenname: Nubia orcidid: 0000-0003-0146-2218 surname: Boechat fullname: Boechat, Nubia – sequence: 12 givenname: Mônica Macedo surname: Bastos fullname: Bastos, Mônica Macedo
BackLink	https://www.ncbi.nlm.nih.gov/pubmed/34621389$$D View this record in MEDLINE/PubMed
BookMark	eNptkkuLFDEUhQsZcR66ci8BNyNOtXlVquJCkMHHwIAudB1SqZvutKmkTaoa2n_gvzZtz8jMIAQSbr57csK5p9VRiAGq6jnBC9YK-qZfR7Mg7YJw_qg6IZ3AdcNke3TnfFyd5rzGmGOBxZPqmHFBCevkSfX7_OsKws7r0YX4arNLbnSDC1CTC3rB6ik5_St6QAMkt9WT20JGuqygfVxmFC1yYykH179FGXQyKxeWyMaEQtyCRyaOmziHobQstQt5QmaVYnAGjTvw0Q3Iw_wDRqefVo-t9hme3exn1fePH75dfq6vv3y6unx_XRveNlPNQOtBcrC9pJKaHjPWEmsFp0MvO9naHgvBLLMd0UQaqtuOyoEyzlnPrMDsrLo66A5Rr9WmfFinnYraqb-FmJZKp8kZD6qhhg-EgpBm4Bhob7gpb_UNQC-AmaL17qC1mfsRBgNhStrfE71_E9xKLeNWdbzBkrMicH4jkOLPGfKkRpcNeK8DxDkr2nRYyJLaHn35AF3HOZUc9pRsaIcx7Qr14q6jf1ZuEy8AOQAmxZwTWGXcVBKMe4POK4LVfqrUfqoUaVWZqtLz-kHPrez_6D_IodFv
CitedBy_id	crossref_primary_10_2174_0115680266332163241127114029 crossref_primary_10_1098_rsos_241654 crossref_primary_10_3390_ph15030309 crossref_primary_10_3390_molecules27030750 crossref_primary_10_2174_0113816128346900241111115125
Cites_doi	10.1016/j.bioorg.2017.01.010 10.1056/nejmoa1609324 10.1039/ps9610000357 10.3390/molecules21070879 10.1590/s1516-84842009005000053 10.1002/1521-3773(20010601)40:11<2004::aid-anie2004>3.0.co;2-5 10.1016/j.bmcl.2016.01.068 10.1107/s2053273314026370 10.1016/j.str.2019.05.012 10.1055/s-2008-1078019 10.1126/science.abc2754 10.1182/blood-2008-04-149286 10.1107/s002188980600731x 10.1038/nsmb.1486 10.1107/s2053229614024218 10.1111/j.1349-7006.2009.01144.x 10.5935/1984-6835.20130023 10.21577/0100-4042.20170027 10.1016/j.bmc.2019.07.005 10.1002/1521-3773(20020715)41:14<2596::aid-anie2596>3.0.co;2-4 10.1080/14737140.2018.1527688 10.1002/ajh.25011 10.1016/j.phrs.2019.03.006 10.1002/cmdc.201100304 10.1007/s00044-017-1993-8 10.1021/acsomega.8b01960 10.1016/j.drudis.2017.05.014 10.1021/acsomega.8b02849 10.1107/s0021889808042726 10.2174/092986712803414213 10.1080/15257770.2018.1485932 10.1046/j.1365-2141.2000.02137.x 10.1021/jm051197e 10.1038/s41392-019-0099-9 10.1021/ci025515j 10.1186/s13045-018-0624-2 10.3109/14756360903524304 10.1039/b913333j 10.1203/01.pdr.0000082017.97479.39 10.1126/science.3263702 10.7897/2230-8407.097121 10.1016/j.chembiol.2010.12.013
ContentType	Journal Article
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.
Copyright_xml	– notice: Copyright © 2021, Pimentel et al. – notice: 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. – notice: Copyright © 2021, Pimentel et al. 2021 Pimentel et al.
DBID	AAYXX CITATION NPM 3V. 7XB 88I 8FE 8FH 8FK ABUWG AFKRA AZQEC BBNVY BENPR BFMQW BHPHI CCPQU DWQXO GNUQQ HCIFZ LK8 M2P M7P PHGZM PHGZT PIMPY PKEHL PQEST PQGLB PQQKQ PQUKI PRINS Q9U 7X8 5PM DOA
DOI	10.3762/bjoc.17.144
DatabaseName	CrossRef PubMed ProQuest Central (Corporate) ProQuest Central (purchase pre-March 2016) Science Database (Alumni Edition) ProQuest SciTech Collection ProQuest Natural Science Collection ProQuest Central (Alumni) (purchase pre-March 2016) ProQuest Central (Alumni) ProQuest Central UK/Ireland ProQuest Central Essentials Biological Science Collection ProQuest Central Continental Europe Database Natural Science Collection ProQuest One Community College ProQuest Central Korea ProQuest Central Student SciTech Premium Collection ProQuest Biological Science Collection Science Database Biological Science Database ProQuest Central Premium ProQuest One Academic (New) Publicly Available Content Database ProQuest One Academic Middle East (New) ProQuest One Academic Eastern Edition (DO NOT USE) ProQuest One Applied & Life Sciences ProQuest One Academic (retired) ProQuest One Academic UKI Edition ProQuest Central China ProQuest Central Basic MEDLINE - Academic PubMed Central (Full Participant titles) DOAJ Directory of Open Access Journals
DatabaseTitle	CrossRef PubMed Publicly Available Content Database ProQuest Central Student ProQuest One Academic Middle East (New) ProQuest Central Essentials ProQuest Central (Alumni Edition) SciTech Premium Collection ProQuest One Community College ProQuest Natural Science Collection ProQuest Central China ProQuest Central ProQuest One Applied & Life Sciences Natural Science Collection ProQuest Central Korea Biological Science Collection ProQuest Central (New) ProQuest Science Journals (Alumni Edition) ProQuest Biological Science Collection ProQuest Central Basic ProQuest Science Journals ProQuest One Academic Eastern Edition Continental Europe Database Biological Science Database ProQuest SciTech Collection ProQuest One Academic UKI Edition ProQuest One Academic ProQuest One Academic (New) ProQuest Central (Alumni) MEDLINE - Academic
DatabaseTitleList	Publicly Available Content Database MEDLINE - Academic PubMed CrossRef
Database_xml	– sequence: 1 dbid: DOA name: DOAJ Directory of Open Access Journals url: https://www.doaj.org/ sourceTypes: Open Website – sequence: 2 dbid: NPM name: PubMed url: http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database – sequence: 3 dbid: PIMPY name: Publicly Available Content Database url: http://search.proquest.com/publiccontent sourceTypes: Aggregation Database
DeliveryMethod	fulltext_linktorsrc
Discipline	Chemistry
EISSN	1860-5397
EndPage	2269
ExternalDocumentID	oai_doaj_org_article_52c4d12e69cd40e2bc4c1ffb5eeb6e3c PMC8450943 34621389 10_3762_bjoc_17_144
Genre	Journal Article
GroupedDBID	23N 2WC 53G 5GY 5VS 6J9 88I 8FE 8FH AAFWJ AAYXX ABUWG ACGFO ACGOD ACPRK ADBBV ADRAZ AENEX AFFHD AFKRA AFPKN ALMA_UNASSIGNED_HOLDINGS AOIJS AZQEC BAWUL BBNVY BCNDV BENPR BFMQW BHPHI BPHCQ CCPQU CITATION CS3 DIK DU5 DWQXO EBS F5P GNUQQ GROUPED_DOAJ GX1 HCIFZ HH5 HYE IAO IHR KQ8 LK8 M2P M48 M7P M~E OK1 OVT P2P PGMZT PHGZM PHGZT PIMPY PQGLB PQQKQ PROAC RNS RPM TR2 WOQ XSB ~9O 4.4 C1A EJD IGS IPNFZ ITC NPM RIG ROL 3V. 7XB 8FK PKEHL PQEST PQUKI PRINS Q9U 7X8 PUEGO 5PM
ID	FETCH-LOGICAL-c475t-3eaad94efb9292cb03371ff642db9897fb0663f3f81a19c2a7829d23443b3f603
IEDL.DBID	M2P
ISICitedReferencesCount	7
ISICitedReferencesURI	http://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestLinkType=CitingArticles&DestApp=WOS_CPL&KeyUT=000703387000001&url=https%3A%2F%2Fcvtisr.summon.serialssolutions.com%2F%23%21%2Fsearch%3Fho%3Df%26include.ft.matches%3Dt%26l%3Dnull%26q%3D
ISSN	1860-5397 2195-951X
IngestDate	Fri Oct 03 12:44:49 EDT 2025 Tue Nov 04 01:59:23 EST 2025 Thu Sep 04 19:08:16 EDT 2025 Fri Jul 25 11:54:07 EDT 2025 Mon Jul 21 06:00:46 EDT 2025 Tue Nov 18 22:17:14 EST 2025 Sat Nov 29 02:06:20 EST 2025
IsDoiOpenAccess	true
IsOpenAccess	true
IsPeerReviewed	true
IsScholarly	true
Issue	1
Keywords	(phenylamino)pyrimidine-pyridine chronic myeloid leukemia imatinib 1,2,3-triazole 1,3-dipolar cycloaddition
Language	English
License	https://creativecommons.org/licenses/by/4.0 Copyright © 2021, Pimentel et al. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms/terms) This is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the author(s) and source are credited and that individual graphics may be subject to special legal provisions.
LinkModel	DirectLink
MergedId	FETCHMERGED-LOGICAL-c475t-3eaad94efb9292cb03371ff642db9897fb0663f3f81a19c2a7829d23443b3f603
Notes	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23
ORCID	0000-0002-1336-5928 0000-0001-7850-3888 0000-0002-0863-7087 0000-0003-0146-2218 0000-0003-3676-5964
OpenAccessLink	https://www.proquest.com/docview/2595280028?pq-origsite=%requestingapplication%
PMID	34621389
PQID	2595280028
PQPubID	2045588
PageCount	10
ParticipantIDs	doaj_primary_oai_doaj_org_article_52c4d12e69cd40e2bc4c1ffb5eeb6e3c pubmedcentral_primary_oai_pubmedcentral_nih_gov_8450943 proquest_miscellaneous_2580690603 proquest_journals_2595280028 pubmed_primary_34621389 crossref_citationtrail_10_3762_bjoc_17_144 crossref_primary_10_3762_bjoc_17_144
PublicationCentury	2000
PublicationDate	2021-09-01
PublicationDateYYYYMMDD	2021-09-01
PublicationDate_xml	– month: 09 year: 2021 text: 2021-09-01 day: 01
PublicationDecade	2020
PublicationPlace	Germany
PublicationPlace_xml	– name: Germany – name: Frankfurt am Main – name: Trakehner Str. 7-9, 60487 Frankfurt am Main, Germany
PublicationTitle	Beilstein journal of organic chemistry
PublicationTitleAlternate	Beilstein J Org Chem
PublicationYear	2021
Publisher	Beilstein-Institut zur Föerderung der Chemischen Wissenschaften Beilstein-Institut
Publisher_xml	– name: Beilstein-Institut zur Föerderung der Chemischen Wissenschaften – name: Beilstein-Institut
References	Rodriguez (ref8) 2007; 19 ref13 ref34 ref15 ref37 ref36 ref31 ref11 ref33 ref10 ref32 ref2 ref1 ref17 ref39 ref16 ref38 ref19 ref18 Badisa (ref35) 2009; 29 ref50 ref24 ref46 ref23 ref45 Nath (ref14) 2011; 2 ref26 ref48 ref25 ref47 ref20 ref22 ref44 ref21 ref43 ref28 ref27 ref49 ref29 ref7 ref9 ref4 ref3 ref6 ref5
References_xml	– ident: ref18 doi: 10.1016/j.bioorg.2017.01.010 – ident: ref11 doi: 10.1056/nejmoa1609324 – ident: ref15 doi: 10.1039/ps9610000357 – ident: ref6 doi: 10.3390/molecules21070879 – ident: ref10 doi: 10.1590/s1516-84842009005000053 – volume: 2 start-page: 1490 year: 2011 ident: ref14 publication-title: International Journal of Research in Ayurveda & Pharmacy – ident: ref16 doi: 10.1002/1521-3773(20010601)40:11<2004::aid-anie2004>3.0.co;2-5 – ident: ref27 doi: 10.1016/j.bmcl.2016.01.068 – ident: ref43 doi: 10.1107/s2053273314026370 – ident: ref50 doi: 10.1016/j.str.2019.05.012 – ident: ref31 doi: 10.1055/s-2008-1078019 – ident: ref33 doi: 10.1126/science.abc2754 – ident: ref3 doi: 10.1182/blood-2008-04-149286 – ident: ref45 doi: 10.1107/s002188980600731x – ident: ref38 doi: 10.1038/nsmb.1486 – ident: ref44 doi: 10.1107/s2053229614024218 – ident: ref47 doi: 10.1111/j.1349-7006.2009.01144.x – ident: ref29 doi: 10.5935/1984-6835.20130023 – ident: ref2 doi: 10.21577/0100-4042.20170027 – ident: ref19 doi: 10.1016/j.bmc.2019.07.005 – ident: ref17 doi: 10.1002/1521-3773(20020715)41:14<2596::aid-anie2596>3.0.co;2-4 – ident: ref9 doi: 10.1080/14737140.2018.1527688 – ident: ref4 doi: 10.1002/ajh.25011 – ident: ref39 doi: 10.1016/j.phrs.2019.03.006 – ident: ref26 doi: 10.1002/cmdc.201100304 – ident: ref13 doi: 10.1007/s00044-017-1993-8 – ident: ref24 doi: 10.1021/acsomega.8b01960 – ident: ref23 doi: 10.1016/j.drudis.2017.05.014 – volume: 29 start-page: 2993 year: 2009 ident: ref35 publication-title: Anticancer Research – ident: ref34 doi: 10.1021/acsomega.8b02849 – ident: ref46 doi: 10.1107/s0021889808042726 – ident: ref22 doi: 10.2174/092986712803414213 – ident: ref36 doi: 10.1080/15257770.2018.1485932 – ident: ref1 doi: 10.1046/j.1365-2141.2000.02137.x – volume: 19 start-page: 287 year: 2007 ident: ref8 publication-title: Rev. Venez. Oncol. – ident: ref49 doi: 10.1021/jm051197e – ident: ref25 doi: 10.1038/s41392-019-0099-9 – ident: ref32 doi: 10.1021/ci025515j – ident: ref7 doi: 10.1186/s13045-018-0624-2 – ident: ref20 doi: 10.3109/14756360903524304 – ident: ref28 doi: 10.1039/b913333j – ident: ref48 doi: 10.1203/01.pdr.0000082017.97479.39 – ident: ref5 doi: 10.1126/science.3263702 – ident: ref21 doi: 10.7897/2230-8407.097121 – ident: ref37 doi: 10.1016/j.chembiol.2010.12.013
SSID	ssj0040606
Score	2.2980587
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...
SourceID	doaj pubmedcentral proquest pubmed crossref
SourceType	Open Website Open Access Repository Aggregation Database Index Database Enrichment Source
StartPage	2260
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
SummonAdditionalLinks	– databaseName: DOAJ Directory of Open Access Journals dbid: DOA link: http://cvtisr.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwrV3LbtUwELVQhQQbxJtAQUbqAlBDE9tJbHZQUbFAVReAuov8mLSB4FS9D-nyB_w1M0nuVS-qxAYpq9iRHM_YcyaenMPYXqiMa6QwaQhepxihQ2qz0qYAmQgKdOYGts9vn6vjY316ak6uSH1RTdhIDzxO3EEhvAq5gNL4oDIQziufN40rAFwJ0tPum1VmnUyNezBGqUFVM9dllhYYcsc_83AxiQP3vfdv84pONbdi0UDZfx3O_Ltc8kr8ObrL7kzAkb8fB3yP3YB4n906XOu1PWC_X52cQ1yhhdvYv75YkV4XBiZI832xL1OS5_jVd8AD-txyoPuecYtXpM83M943vCX0Glv3jk8HDPGMI6blsV9Cx6n4nDSY8JEz2yKq5H4k1uU_V9D1beAdLH7gcOxD9vXo45fDT-kktJB6VRXzVIK1wShoHIIl4V0mZYVzjKlJcEabqnEETBrZ6NzmxguLsMIEIZWSTjZlJh-xndhHeMK4EbaxGWmhaq2MLKwKJWbg4EyorAafsDfrKa_9xEJOYhhdjdkI2acm-9R5hTmJStjepvPFSL5xfbcPZLtNF2LMHm6gH9WTH9X_8qOE7a4tX0_LeFZjblgIgtQ6YS83zWhXOlWxEfoF9dED23MmE_Z4dJTNSKQqBZ0EJ6zacqGtoW63xPZ8IPnWiqgN5dP_8W7P2G1BpThDadwu25lfLuA5u-mX83Z2-WJYOX8AxZUkJw priority: 102 providerName: Directory of Open Access Journals
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
WOSCitedRecordID	wos000703387000001&url=https%3A%2F%2Fcvtisr.summon.serialssolutions.com%2F%23%21%2Fsearch%3Fho%3Df%26include.ft.matches%3Dt%26l%3Dnull%26q%3D
hasFullText	1
inHoldings	1
isFullTextHit
isPrint
journalDatabaseRights	– providerCode: PRVAON databaseName: DOAJ Directory of Open Access Journals customDbUrl: eissn: 1860-5397 dateEnd: 99991231 omitProxy: false ssIdentifier: ssj0040606 issn: 1860-5397 databaseCode: DOA dateStart: 20050101 isFulltext: true titleUrlDefault: https://www.doaj.org/ providerName: Directory of Open Access Journals – providerCode: PRVHPJ databaseName: ROAD: Directory of Open Access Scholarly Resources customDbUrl: eissn: 1860-5397 dateEnd: 99991231 omitProxy: false ssIdentifier: ssj0040606 issn: 1860-5397 databaseCode: M~E dateStart: 20050101 isFulltext: true titleUrlDefault: https://road.issn.org providerName: ISSN International Centre – providerCode: PRVPQU databaseName: Biological Science Database customDbUrl: eissn: 1860-5397 dateEnd: 99991231 omitProxy: false ssIdentifier: ssj0040606 issn: 1860-5397 databaseCode: M7P dateStart: 20150101 isFulltext: true titleUrlDefault: http://search.proquest.com/biologicalscijournals providerName: ProQuest – providerCode: PRVPQU databaseName: Continental Europe Database (ProQuest) customDbUrl: eissn: 1860-5397 dateEnd: 99991231 omitProxy: false ssIdentifier: ssj0040606 issn: 1860-5397 databaseCode: BFMQW dateStart: 20150101 isFulltext: true titleUrlDefault: https://search.proquest.com/conteurope providerName: ProQuest – providerCode: PRVPQU databaseName: ProQuest Central customDbUrl: eissn: 1860-5397 dateEnd: 99991231 omitProxy: false ssIdentifier: ssj0040606 issn: 1860-5397 databaseCode: BENPR dateStart: 20150101 isFulltext: true titleUrlDefault: https://www.proquest.com/central providerName: ProQuest – providerCode: PRVPQU databaseName: Publicly Available Content Database customDbUrl: eissn: 1860-5397 dateEnd: 99991231 omitProxy: false ssIdentifier: ssj0040606 issn: 1860-5397 databaseCode: PIMPY dateStart: 20150101 isFulltext: true titleUrlDefault: http://search.proquest.com/publiccontent providerName: ProQuest – providerCode: PRVPQU databaseName: Science Database customDbUrl: eissn: 1860-5397 dateEnd: 99991231 omitProxy: false ssIdentifier: ssj0040606 issn: 1860-5397 databaseCode: M2P dateStart: 20150101 isFulltext: true titleUrlDefault: https://search.proquest.com/sciencejournals providerName: ProQuest
link	http://cvtisr.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV1bb9MwFLbYigQv3GGFURlpD4AWlthOYvOC2LQKJFoFxKV7inxLl1GS0ptU_gH_Gh83LRRNvCBVqdQ40qnOsc9nn5PvQ-jApEIVlIjAGM0Dl6FNIMNEBtaGxDDLQ-XZPj-_S_t9PhiIrDlwmzZtles10S_UptZwRn7kYHpMAN3wV-PvAahGQXW1kdDYQS2HbCJo6eqRbL0Su1zltTWJ1yOMo8Hq_Tw3pciRuqj1iyiF2uZWRvLE_Zehzb-bJv_IQt2b_2v_LXSjwZ_49SpgbqMrtrqDrp2sZd_uop9Ps3NbLV2glFX9bLwE2S-X32wQHZJDGoDKx496ZLFxobvwrOFTLN2nglOgKa4LXAIIrkr1Ejd1imqIHTTGVb2wIww97CDl5B4ZytKBU6xX_Lz429KO6tLgkZ1_debIe-hT9_TjyZug0WsINEvjWUCtlEYwWyiHuYhWIaVpVBRuh2OU4CItFOCbghY8kpHQRDp0IgyhjFFFiySk99FuVVd2D2FBZCFDkFTlnAkaS2YSt5G3SphUcqvb6PnaZ7luyMxBU2OUu00NODgHB-dR6rY2rI0ONoPHKw6Py4cdg_M3Q4B42_9QT4Z5M4_zmGhmImIToQ0LLVGaafcfVWytSix1hu2v3Z83q8E0_-37Nnqyue38CsUZWdl6DmO4J40OaRs9WEXaxhLKEgIF5TZKt2Jwy9TtO1V57rnCOQOGRPrw32Y9QtcJ9Or43rl9tDubzO1jdFUvZuV00kE76YB3UOv4tJ99gO9u7_2Xjj-96PgJB9fUXVvZ21529gsphzgq
linkProvider	ProQuest
linkToHtml	http://cvtisr.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMw1V3ZbtNAFB2VglRe2JdAgUEqEqCa2jPjZZAQgkLVqiHqQ0F5M7M5NQQ7ZEPhD_gZvpF7vQSCKt76gJSneBJd23c543t9DiFbNpY640x61prEgwptPeVHynPOZ1a4xNcV2-eHbtzrJf2-PFojP9t3YXCsss2JVaK2pcFn5DsA00OG6CZ5OfrqoWoUdldbCY3aLQ7d4hts2SYvDt7A_X3E2N7b4919r1EV8IyIw6nHnVJWCpdpQAbMaJ_zOMgywOFWy0TGmcYqnPEsCVQgDVNQQ6VlXAiueRb5HP73HDkvkFkMRwXZUZv5oTZWWp6s0j8Mg379PiCEMNvRn0rzLIixl7pSASuhgNPQ7d9Dmn9Uvb3L_9v1ukIuNfiavqoD4ipZc8U1srHbytpdJz8eH524YgGBkBflk9ECZc2gfjsv2Gbb3EMVk-_l0FELoTmvWNEnVMGnwKdcE1pmNEeQX-T6OW36MMWAAvSnRTl3Q4oz-ihVBT8ZqBzANzU1_zD9snDDMrd06GafwRx1g7w_kytxk6wXZeFuEyqZypSPkrFJIiQPlbCRiKTT0sYqcaZDnrY-kpqGrB01Q4YpbNrQoVJ0qDSIYesmOmRruXhUc5Scvuw1OttyCRKLV1-U40Ha5Kk0ZEbYgLlIGit8x7QRBs5Rh87pyHEwbLN1t7TJdpP0t691yMPlYbiv2HxShStnuCapSLF93iG3as9eWsJFxLBh3iHxis-vmLp6pMhPKi70RCADJL_zb7MekI3943fdtHvQO7xLLjKcS6rmBDfJ-nQ8c_fIBTOf5pPx_SqgKfl41hHxC8IzjKA
linkToPdf	http://cvtisr.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMw1V3bbtNAEF2VFAEv3C-BAotUJEA1sXfX9i4SQrQlomqJWolL3szenBqCHXJD4Q_4Jb6OHV8CQRVvfUDyk722xvaZnVnP-ByENk0sVEqJ8IzR3HMR2njSj6RnrU8Ms9xXJdvn-4O41-P9vjhcQz-bf2GgrbKZE8uJ2hQavpF3XJoeEshueCet2yIOd7svRl89UJCCSmsjp1FBZN8uvrnl2-T53q571w8J6b56u_PaqxUGPM3icOpRK6URzKbKZQlEK5_SOEhTl5MbJbiIUwUROaUpD2QgNJEungpDKGNU0TTyqbvuGbTOo4j7LbS-3X1z9KGJAy5SlsqepFRDDIN-9Xegc2jSUZ8K_TSIobK6Eg9L2YCTct2_Wzb_iIHdS__z07uMLtaZN35ZucoVtGbzq-j8TiN4dw39eHR4bPOFc5EsLx6PFiB45iK79YItskU90Df5XgwtNs5p5yVf-gRLt-Xw_WuCixRnkP7nmXqG6wpNPsBuUYDzYm6HGLr3QcTKnTKQmUvLsa6YifGXhR0WmcFDO_vszJHX0btTeRI3UCsvcnsLYUFkKn0Qk-WcCRpKZiIWCauEiSW3uo2eNHhJdE3jDmoiw8Qt5wBcCYArCWK3qGNttLkcPKrYS04etg3AWw4ByvFyRzEeJPUMloREMxMQGwltmG-J0ky7e1ShtSqy1Bm20UAvqefBSfIbd230YHnYvVcoS8ncFjMYw0u6bJ-20c0K5UtLKIsIlNLbKF7B_4qpq0fy7LhkSecMuCHp7X-bdR-dc46QHOz19u-gCwQalsoGwg3Umo5n9i46q-fTbDK-V3s3Rh9P2yV-ARLFlsk
openUrl	ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=%28Phenylamino%29pyrimidine-1%2C2%2C3-triazole+derivatives+as+analogs+of+imatinib%3A+searching+for+novel+compounds+against+chronic+myeloid+leukemia&rft.jtitle=Beilstein+journal+of+organic+chemistry&rft.au=Pimentel+Luiz+Claudio+Ferreira&rft.au=Hoelz+Lucas+Villas+Boas&rft.au=Canzian+Henayle+Fernandes&rft.au=Branco+Frederico+Silva+Castelo&rft.date=2021-09-01&rft.pub=Beilstein-Institut+zur+F%C3%B6erderung+der+Chemischen+Wissenschaften&rft.issn=2195-951X&rft.eissn=1860-5397&rft.volume=17&rft.spage=2260&rft.epage=2269&rft_id=info:doi/10.3762%2Fbjoc.17.144&rft.externalDBID=HAS_PDF_LINK
thumbnail_l	http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1860-5397&client=summon
thumbnail_m	http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1860-5397&client=summon
thumbnail_s	http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1860-5397&client=summon