Synthesis of 5,6-dihydropyrrolo[2,1-a]isoquinolines featuring an intramolecular radical-oxidative cyclization of polysubstituted pyrroles, and evaluation of their cytotoxic activity
A three-step protocol for the synthesis of 1,2,3,8,9-pentasubstituted-5,6-dihydropyrrolo[2,1-a]isoquinolines is described, using van Leusen's polysubstituted pyrrole construction followed by intramolecular radical-oxidative cyclization of the isoquinoline system. The cytotoxic activities of the...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2010-10, Vol.8 (19), p.4374-4382 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Reyes-Gutiérrez, Paul E Camacho, José R Ramírez-Apan, Maria Teresa Osornio, Yazmin M Martínez, Roberto |
| description | A three-step protocol for the synthesis of 1,2,3,8,9-pentasubstituted-5,6-dihydropyrrolo[2,1-a]isoquinolines is described, using van Leusen's polysubstituted pyrrole construction followed by intramolecular radical-oxidative cyclization of the isoquinoline system. The cytotoxic activities of the dihydropyrroloisoquinolines were tested on six tumor cell lines. Preliminary structure-activity studies revealed the importance of the identity of the aromatic substituent at the C-2 position, particularly a phenyl, m-(amino) phenyl or m-(cyclohexylmethylpiperazinamide) phenyl substituent, for cytotoxic activity. |
| doi_str_mv | 10.1039/c004399k |
| format | Article |
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The cytotoxic activities of the dihydropyrroloisoquinolines were tested on six tumor cell lines. Preliminary structure-activity studies revealed the importance of the identity of the aromatic substituent at the C-2 position, particularly a phenyl, m-(amino) phenyl or m-(cyclohexylmethylpiperazinamide) phenyl substituent, for cytotoxic activity.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/c004399k</identifier><identifier>PMID: 20672155</identifier><language>eng</language><publisher>England</publisher><subject>Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Cyclization ; Drug Screening Assays, Antitumor ; Humans ; Isoquinolines - chemical synthesis ; Isoquinolines - chemistry ; Isoquinolines - pharmacology ; Models, Molecular ; Neoplasms - drug therapy ; Oxidation-Reduction ; Pyrroles - chemical synthesis ; Pyrroles - chemistry ; Pyrroles - pharmacology ; Structure-Activity Relationship</subject><ispartof>Organic & biomolecular chemistry, 2010-10, Vol.8 (19), p.4374-4382</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c282t-5be8e396875fa21cd20bfa78a48171db4cbdaa18334537dfa8591ea929fd22653</citedby><cites>FETCH-LOGICAL-c282t-5be8e396875fa21cd20bfa78a48171db4cbdaa18334537dfa8591ea929fd22653</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20672155$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Reyes-Gutiérrez, Paul E</creatorcontrib><creatorcontrib>Camacho, José R</creatorcontrib><creatorcontrib>Ramírez-Apan, Maria Teresa</creatorcontrib><creatorcontrib>Osornio, Yazmin M</creatorcontrib><creatorcontrib>Martínez, Roberto</creatorcontrib><title>Synthesis of 5,6-dihydropyrrolo[2,1-a]isoquinolines featuring an intramolecular radical-oxidative cyclization of polysubstituted pyrroles, and evaluation of their cytotoxic activity</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>A three-step protocol for the synthesis of 1,2,3,8,9-pentasubstituted-5,6-dihydropyrrolo[2,1-a]isoquinolines is described, using van Leusen's polysubstituted pyrrole construction followed by intramolecular radical-oxidative cyclization of the isoquinoline system. The cytotoxic activities of the dihydropyrroloisoquinolines were tested on six tumor cell lines. Preliminary structure-activity studies revealed the importance of the identity of the aromatic substituent at the C-2 position, particularly a phenyl, m-(amino) phenyl or m-(cyclohexylmethylpiperazinamide) phenyl substituent, for cytotoxic activity.</description><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Cyclization</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Humans</subject><subject>Isoquinolines - chemical synthesis</subject><subject>Isoquinolines - chemistry</subject><subject>Isoquinolines - pharmacology</subject><subject>Models, Molecular</subject><subject>Neoplasms - drug therapy</subject><subject>Oxidation-Reduction</subject><subject>Pyrroles - chemical synthesis</subject><subject>Pyrroles - chemistry</subject><subject>Pyrroles - pharmacology</subject><subject>Structure-Activity Relationship</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kctu1TAQhi1ERS8g8QTIO1ictL7EcbxEVaFIlVhQVghFE3tCDT7xwXYqwnvxfrg67VnNLD59_4x-Ql5zds6ZNBeWsVYa8-sZOeGt1g1T0jw_7IIdk9OcfzLGje7aF-RYsE4LrtQJ-fdlncsdZp9pnKjadI3zd6tLcbemFEP8Jja8ge8-x9-Ln2PwM2Y6IZQl-fkHhZn6uSTYxoB2CZBoAucthCb-8Q6Kv0dqVxv837rH-SFjF8OalzEXX5aCju6DMG-qzFG8h7Ac2HqZT1VQYqk-S8FWoy_rS3I0Qcj46nGeka8frm4vr5ubzx8_Xb6_aazoRWnUiD1K0_VaTSC4dYKNE-ge2p5r7sbWjg6A91K2Smo3Qa8MRzDCTE6ITskz8nbv3aX6P-YybH22GALMGJc8aNUy0XJuKvluT9oUc044Dbvkt5DWgbPhoaPhqaOKvnmULuMW3QF8KkX-Bym1kko</recordid><startdate>20101007</startdate><enddate>20101007</enddate><creator>Reyes-Gutiérrez, Paul E</creator><creator>Camacho, José R</creator><creator>Ramírez-Apan, Maria Teresa</creator><creator>Osornio, Yazmin M</creator><creator>Martínez, Roberto</creator><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>20101007</creationdate><title>Synthesis of 5,6-dihydropyrrolo[2,1-a]isoquinolines featuring an intramolecular radical-oxidative cyclization of polysubstituted pyrroles, and evaluation of their cytotoxic activity</title><author>Reyes-Gutiérrez, Paul E ; 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| ispartof | Organic & biomolecular chemistry, 2010-10, Vol.8 (19), p.4374-4382 |
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| source | MEDLINE; Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
| subjects | Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Cell Line, Tumor Cell Proliferation - drug effects Cyclization Drug Screening Assays, Antitumor Humans Isoquinolines - chemical synthesis Isoquinolines - chemistry Isoquinolines - pharmacology Models, Molecular Neoplasms - drug therapy Oxidation-Reduction Pyrroles - chemical synthesis Pyrroles - chemistry Pyrroles - pharmacology Structure-Activity Relationship |
| title | Synthesis of 5,6-dihydropyrrolo[2,1-a]isoquinolines featuring an intramolecular radical-oxidative cyclization of polysubstituted pyrroles, and evaluation of their cytotoxic activity |
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