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
[Display omitted] •New green and efficient methodology for Atwal reaction.•Various new aminopyrimidine and pyrazole with ferrocene were synthetized.•Crystal structures were determined.•The antiproliferative activity of all compounds were determined in four human cancer line cell.•Docking and Machine...
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Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2021-09, Vol.48, p.128240-128240, Article 128240 |
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creator | 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. |
description | [Display omitted]
•New green and efficient methodology for Atwal reaction.•Various new aminopyrimidine and pyrazole with ferrocene were synthetized.•Crystal structures were determined.•The antiproliferative activity of all compounds were determined in four human cancer line cell.•Docking and Machine Learning studies were conducted corroborating the experimental data.
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. |
doi_str_mv | 10.1016/j.bmcl.2021.128240 |
format | Article |
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•New green and efficient methodology for Atwal reaction.•Various new aminopyrimidine and pyrazole with ferrocene were synthetized.•Crystal structures were determined.•The antiproliferative activity of all compounds were determined in four human cancer line cell.•Docking and Machine Learning studies were conducted corroborating the experimental data.
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.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2021.128240</identifier><identifier>PMID: 34217828</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Antiproliferative activity ; Atwal reaction ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Computational studies ; Dose-Response Relationship, Drug ; Drug Screening Assays, Antitumor ; Ferrocene ; Ferrous Compounds - chemical synthesis ; Ferrous Compounds - chemistry ; Ferrous Compounds - pharmacology ; Humans ; Machine Learning ; Metallocenes - chemical synthesis ; Metallocenes - chemistry ; Metallocenes - pharmacology ; Microwaves ; Molecular Docking Simulation ; Molecular Structure ; Pyrazoles - chemical synthesis ; Pyrazoles - chemistry ; Pyrazoles - pharmacology ; Pyrimidine ; Pyrimidines - chemical synthesis ; Pyrimidines - chemistry ; Pyrimidines - pharmacology ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry letters, 2021-09, Vol.48, p.128240-128240, Article 128240</ispartof><rights>2021 Elsevier Ltd</rights><rights>Copyright © 2021 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c356t-cdd482368340a65bfa557351077bdad8a84431ab17487f0228f9c264ff4547c63</citedby><cites>FETCH-LOGICAL-c356t-cdd482368340a65bfa557351077bdad8a84431ab17487f0228f9c264ff4547c63</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2021.128240$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34217828$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Filho, Eclair Venturini</creatorcontrib><creatorcontrib>Pina, Jorge W.S.</creatorcontrib><creatorcontrib>Antoniazi, Mariana K.</creatorcontrib><creatorcontrib>Loureiro, Laiza B.</creatorcontrib><creatorcontrib>Ribeiro, Marcos A.</creatorcontrib><creatorcontrib>Pinheiro, Carlos B.</creatorcontrib><creatorcontrib>Guimarães, Celina J.</creatorcontrib><creatorcontrib>de Oliveira, Fátima C.E.</creatorcontrib><creatorcontrib>Pessoa, Claudia</creatorcontrib><creatorcontrib>Taranto, Alex G.</creatorcontrib><creatorcontrib>Greco, Sandro J.</creatorcontrib><title>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</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
•New green and efficient methodology for Atwal reaction.•Various new aminopyrimidine and pyrazole with ferrocene were synthetized.•Crystal structures were determined.•The antiproliferative activity of all compounds were determined in four human cancer line cell.•Docking and Machine Learning studies were conducted corroborating the experimental data.
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.</description><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Antiproliferative activity</subject><subject>Atwal reaction</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Computational studies</subject><subject>Dose-Response Relationship, Drug</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Ferrocene</subject><subject>Ferrous Compounds - chemical synthesis</subject><subject>Ferrous Compounds - chemistry</subject><subject>Ferrous Compounds - pharmacology</subject><subject>Humans</subject><subject>Machine Learning</subject><subject>Metallocenes - chemical synthesis</subject><subject>Metallocenes - chemistry</subject><subject>Metallocenes - pharmacology</subject><subject>Microwaves</subject><subject>Molecular Docking Simulation</subject><subject>Molecular Structure</subject><subject>Pyrazoles - chemical synthesis</subject><subject>Pyrazoles - chemistry</subject><subject>Pyrazoles - pharmacology</subject><subject>Pyrimidine</subject><subject>Pyrimidines - chemical synthesis</subject><subject>Pyrimidines - chemistry</subject><subject>Pyrimidines - pharmacology</subject><subject>Structure-Activity Relationship</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9UcFu1DAQjRCIlsIPcEA-cqi3tuM4XolLVRWKVAkkQOJmTexJ10sSL7Z3q_DH_AUOW-DGwRrr-c3zm3lV9ZKzFWdcXWxX3WiHlWCCr7jQQrJH1SmXStJasuZxdcrWilG9ll9PqmcpbRnjkkn5tDqppeCtFvq0-vlpnvIGk0_nxAX7zU9352QEu_ETkgEhTgUhMLlyst_FMPgeI2R_QAK2FJ9nEnpSNIii5SkGixNebDBjuc52QCoojH4Kuzn60btFeNFr_rEpv6Ef5wg_woDEYfSH3x8kEroMhe9IN5PR2xju4YAUUrGbC3qZ72EgERcjYSKQyC5kLD4Luti1MFmMBO4Klp5XT3oYEr54qGfVl7fXn69u6O2Hd--vLm-prRuVqXVOalErXXYIqul6aJq2bjhr286B06ClrDl0vJW67ZkQul9boWTfy0a2VtVn1eujblnW9z2mbEafLA4DTBj2yYhGaiVUzetCFUdqmSyliL3ZlRVBnA1nZonYbM0SsVkiNseIS9OrB_19N6L72_In00J4cyRgmfLgMZpkPZZNOB_RZuOC_5_-L7iyvcQ</recordid><startdate>20210915</startdate><enddate>20210915</enddate><creator>Filho, Eclair Venturini</creator><creator>Pina, Jorge W.S.</creator><creator>Antoniazi, Mariana K.</creator><creator>Loureiro, Laiza B.</creator><creator>Ribeiro, Marcos A.</creator><creator>Pinheiro, Carlos B.</creator><creator>Guimarães, Celina J.</creator><creator>de Oliveira, Fátima C.E.</creator><creator>Pessoa, Claudia</creator><creator>Taranto, Alex G.</creator><creator>Greco, Sandro J.</creator><general>Elsevier Ltd</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20210915</creationdate><title>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</title><author>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.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-cdd482368340a65bfa557351077bdad8a84431ab17487f0228f9c264ff4547c63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Antiproliferative activity</topic><topic>Atwal reaction</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>Computational studies</topic><topic>Dose-Response Relationship, Drug</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Ferrocene</topic><topic>Ferrous Compounds - chemical synthesis</topic><topic>Ferrous Compounds - chemistry</topic><topic>Ferrous Compounds - pharmacology</topic><topic>Humans</topic><topic>Machine Learning</topic><topic>Metallocenes - chemical synthesis</topic><topic>Metallocenes - chemistry</topic><topic>Metallocenes - pharmacology</topic><topic>Microwaves</topic><topic>Molecular Docking Simulation</topic><topic>Molecular Structure</topic><topic>Pyrazoles - chemical synthesis</topic><topic>Pyrazoles - chemistry</topic><topic>Pyrazoles - pharmacology</topic><topic>Pyrimidine</topic><topic>Pyrimidines - chemical synthesis</topic><topic>Pyrimidines - chemistry</topic><topic>Pyrimidines - pharmacology</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Filho, Eclair Venturini</creatorcontrib><creatorcontrib>Pina, Jorge W.S.</creatorcontrib><creatorcontrib>Antoniazi, Mariana K.</creatorcontrib><creatorcontrib>Loureiro, Laiza B.</creatorcontrib><creatorcontrib>Ribeiro, Marcos A.</creatorcontrib><creatorcontrib>Pinheiro, Carlos B.</creatorcontrib><creatorcontrib>Guimarães, Celina J.</creatorcontrib><creatorcontrib>de Oliveira, Fátima C.E.</creatorcontrib><creatorcontrib>Pessoa, Claudia</creatorcontrib><creatorcontrib>Taranto, Alex G.</creatorcontrib><creatorcontrib>Greco, Sandro J.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Filho, Eclair Venturini</au><au>Pina, Jorge W.S.</au><au>Antoniazi, Mariana K.</au><au>Loureiro, Laiza B.</au><au>Ribeiro, Marcos A.</au><au>Pinheiro, Carlos B.</au><au>Guimarães, Celina J.</au><au>de Oliveira, Fátima C.E.</au><au>Pessoa, Claudia</au><au>Taranto, Alex G.</au><au>Greco, Sandro J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>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</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2021-09-15</date><risdate>2021</risdate><volume>48</volume><spage>128240</spage><epage>128240</epage><pages>128240-128240</pages><artnum>128240</artnum><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
•New green and efficient methodology for Atwal reaction.•Various new aminopyrimidine and pyrazole with ferrocene were synthetized.•Crystal structures were determined.•The antiproliferative activity of all compounds were determined in four human cancer line cell.•Docking and Machine Learning studies were conducted corroborating the experimental data.
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.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>34217828</pmid><doi>10.1016/j.bmcl.2021.128240</doi><tpages>1</tpages></addata></record> |
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subjects | Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Antiproliferative activity Atwal reaction Cell Line, Tumor Cell Proliferation - drug effects Computational studies Dose-Response Relationship, Drug Drug Screening Assays, Antitumor Ferrocene Ferrous Compounds - chemical synthesis Ferrous Compounds - chemistry Ferrous Compounds - pharmacology Humans Machine Learning Metallocenes - chemical synthesis Metallocenes - chemistry Metallocenes - pharmacology Microwaves Molecular Docking Simulation Molecular Structure Pyrazoles - chemical synthesis Pyrazoles - chemistry Pyrazoles - pharmacology Pyrimidine Pyrimidines - chemical synthesis Pyrimidines - chemistry Pyrimidines - pharmacology Structure-Activity Relationship |
title | 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 |
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