Synthesis and Biological Activities of Camphor Hydrazone and Imine Derivatives
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2016 |
| Outros Autores: | , , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Institucional da FIOCRUZ (ARCA) |
| Texto Completo: | https://www.arca.fiocruz.br/handle/icict/60703 |
Resumo: | The authors would like to acknowledge CNPq and Fiocruz for financial and infrastructure assistance. |
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Silva, Emerson T. daAraújo, Adriele da SilvaMoraes, Adriana M.Souza, Leidiane A. deLourenço, Maria Cristina SilvaSouza, Marcus V. N. deWardell, James L.Wardell, Solange M. S. V.2023-10-04T23:21:51Z2023-10-04T23:21:51Z2016SILVA, Emerson T. da et al. Synthesis and Biological Activities of Camphor Hydrazone and Imine Derivatives. Scientia Pharmaceutica, v. 84, n. 3, p. 467-483, Oct. 2016.0036-8709https://www.arca.fiocruz.br/handle/icict/6070310.3390/scipharm840304672218-0532The authors would like to acknowledge CNPq and Fiocruz for financial and infrastructure assistance.Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos (Farmanguinhos). Rio de Janeiro, RJ, Brazil.Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos (Farmanguinhos). Rio de Janeiro, RJ, Brazil.Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos (Farmanguinhos). Rio de Janeiro, RJ, Brazil.Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos (Farmanguinhos). Rio de Janeiro, RJ, Brazil.Fundação Oswaldo Cruz. Instituto Nacional de Infectologia Evandro Chagas. Rio de Janeiro, RJ, Brazil.Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos (Farmanguinhos). Rio de Janeiro, RJ, Brazil.Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos (Farmanguinhos). Rio de Janeiro, RJ, Brazil / University of Aberdeen. Department of Chemistry. Aberdeen, Scotland, UK.CHEMSOL. Aberdeen, Scotland, UK.Both sonochemical and classical methodologies have been employed to convert camphor, 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one, C₉H16C=O, into a number of derivatives including hydrazones, C₉H16C=N-NHAr 3, imines, C₉H16C=N-R 7, and the key intermediate nitroimine, C₉H16C=N-NO₂ 6. Reactions of nitroamine 6 with nucleophiles by classical methods provided the desired compounds in a range of yields. In evaluations of activity against Mycobacterium tuberculosis, compound 7j exhibited the best activity (minimal inhibitory concentration (MIC) = 3.12 µg/mL), comparable to that of the antitubercular drug ethambutol. The other derivatives displayed modest antimycobacterial activities at 25-50 µg/mL. In in vitro tests against cancer cell lines, none of the synthesized camphor compounds exhibited cytotoxic activities.engÖsterreichische Apotheker-VerlagsgesellschaftSynthesis and Biological Activities of Camphor Hydrazone and Imine Derivativesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleCamphorHydrazonesIminesSonochemistryTuberculosisinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txtlicense.txttext/plain; charset=utf-82991https://www.arca.fiocruz.br/bitstream/icict/60703/1/license.txt5a560609d32a3863062d77ff32785d58MD51ORIGINALve_Emerson_Silva_etal_INI_FAR_2016.pdfve_Emerson_Silva_etal_INI_FAR_2016.pdfapplication/pdf6801816https://www.arca.fiocruz.br/bitstream/icict/60703/2/ve_Emerson_Silva_etal_INI_FAR_2016.pdf51f0526dbbc7bda07fe14a8fe4399fedMD52icict/607032023-10-04 20:23:53.197oai:www.arca.fiocruz.br:icict/60703Q0VTU8ODTyBOw4NPIEVYQ0xVU0lWQSBERSBESVJFSVRPUyBBVVRPUkFJUwoKQW8gYWNlaXRhciBvcyBURVJNT1MgZSBDT05EScOHw5VFUyBkZXN0YSBDRVNTw4NPLCBvIEFVVE9SIGUvb3UgVElUVUxBUiBkZSBkaXJlaXRvcwphdXRvcmFpcyBzb2JyZSBhIE9CUkEgZGUgcXVlIHRyYXRhIGVzdGUgZG9jdW1lbnRvOgoKKDEpIENFREUgZSBUUkFOU0ZFUkUsIHRvdGFsIGUgZ3JhdHVpdGFtZW50ZSwgw6AgRklPQ1JVWiAtIEZVTkRBw4fDg08gT1NXQUxETyBDUlVaLCBlbQpjYXLDoXRlciBwZXJtYW5lbnRlLCBpcnJldm9nw6F2ZWwgZSBOw4NPIEVYQ0xVU0lWTywgdG9kb3Mgb3MgZGlyZWl0b3MgcGF0cmltb25pYWlzIE7Dg08KQ09NRVJDSUFJUyBkZSB1dGlsaXphw6fDo28gZGEgT0JSQSBhcnTDrXN0aWNhIGUvb3UgY2llbnTDrWZpY2EgaW5kaWNhZGEgYWNpbWEsIGluY2x1c2l2ZSBvcyBkaXJlaXRvcwpkZSB2b3ogZSBpbWFnZW0gdmluY3VsYWRvcyDDoCBPQlJBLCBkdXJhbnRlIHRvZG8gbyBwcmF6byBkZSBkdXJhw6fDo28gZG9zIGRpcmVpdG9zIGF1dG9yYWlzLCBlbQpxdWFscXVlciBpZGlvbWEgZSBlbSB0b2RvcyBvcyBwYcOtc2VzOwoKKDIpIEFDRUlUQSBxdWUgYSBjZXNzw6NvIHRvdGFsIG7Do28gZXhjbHVzaXZhLCBwZXJtYW5lbnRlIGUgaXJyZXZvZ8OhdmVsIGRvcyBkaXJlaXRvcyBhdXRvcmFpcwpwYXRyaW1vbmlhaXMgbsOjbyBjb21lcmNpYWlzIGRlIHV0aWxpemHDp8OjbyBkZSBxdWUgdHJhdGEgZXN0ZSBkb2N1bWVudG8gaW5jbHVpLCBleGVtcGxpZmljYXRpdmFtZW50ZSwKb3MgZGlyZWl0b3MgZGUgZGlzcG9uaWJpbGl6YcOnw6NvIGUgY29tdW5pY2HDp8OjbyBww7pibGljYSBkYSBPQlJBLCBlbSBxdWFscXVlciBtZWlvIG91IHZlw61jdWxvLAppbmNsdXNpdmUgZW0gUmVwb3NpdMOzcmlvcyBEaWdpdGFpcywgYmVtIGNvbW8gb3MgZGlyZWl0b3MgZGUgcmVwcm9kdcOnw6NvLCBleGliacOnw6NvLCBleGVjdcOnw6NvLApkZWNsYW1hw6fDo28sIHJlY2l0YcOnw6NvLCBleHBvc2nDp8OjbywgYXJxdWl2YW1lbnRvLCBpbmNsdXPDo28gZW0gYmFuY28gZGUgZGFkb3MsIHByZXNlcnZhw6fDo28sIGRpZnVzw6NvLApkaXN0cmlidWnDp8OjbywgZGl2dWxnYcOnw6NvLCBlbXByw6lzdGltbywgdHJhZHXDp8OjbywgZHVibGFnZW0sIGxlZ2VuZGFnZW0sIGluY2x1c8OjbyBlbSBub3ZhcyBvYnJhcyBvdQpjb2xldMOibmVhcywgcmV1dGlsaXphw6fDo28sIGVkacOnw6NvLCBwcm9kdcOnw6NvIGRlIG1hdGVyaWFsIGRpZMOhdGljbyBlIGN1cnNvcyBvdSBxdWFscXVlciBmb3JtYSBkZQp1dGlsaXphw6fDo28gbsOjbyBjb21lcmNpYWw7CgooMykgUkVDT05IRUNFIHF1ZSBhIGNlc3PDo28gYXF1aSBlc3BlY2lmaWNhZGEgY29uY2VkZSDDoCBGSU9DUlVaIC0gRlVOREHDh8ODTyBPU1dBTERPCkNSVVogbyBkaXJlaXRvIGRlIGF1dG9yaXphciBxdWFscXVlciBwZXNzb2Eg4oCTIGbDrXNpY2Egb3UganVyw61kaWNhLCBww7pibGljYSBvdSBwcml2YWRhLCBuYWNpb25hbCBvdQplc3RyYW5nZWlyYSDigJMgYSBhY2Vzc2FyIGUgdXRpbGl6YXIgYW1wbGFtZW50ZSBhIE9CUkEsIHNlbSBleGNsdXNpdmlkYWRlLCBwYXJhIHF1YWlzcXVlcgpmaW5hbGlkYWRlcyBuw6NvIGNvbWVyY2lhaXM7CgooNCkgREVDTEFSQSBxdWUgYSBvYnJhIMOpIGNyaWHDp8OjbyBvcmlnaW5hbCBlIHF1ZSDDqSBvIHRpdHVsYXIgZG9zIGRpcmVpdG9zIGFxdWkgY2VkaWRvcyBlIGF1dG9yaXphZG9zLApyZXNwb25zYWJpbGl6YW5kby1zZSBpbnRlZ3JhbG1lbnRlIHBlbG8gY29udGXDumRvIGUgb3V0cm9zIGVsZW1lbnRvcyBxdWUgZmF6ZW0gcGFydGUgZGEgT0JSQSwKaW5jbHVzaXZlIG9zIGRpcmVpdG9zIGRlIHZveiBlIGltYWdlbSB2aW5jdWxhZG9zIMOgIE9CUkEsIG9icmlnYW5kby1zZSBhIGluZGVuaXphciB0ZXJjZWlyb3MgcG9yCmRhbm9zLCBiZW0gY29tbyBpbmRlbml6YXIgZSByZXNzYXJjaXIgYSBGSU9DUlVaIC0gRlVOREHDh8ODTyBPU1dBTERPIENSVVogZGUKZXZlbnR1YWlzIGRlc3Blc2FzIHF1ZSB2aWVyZW0gYSBzdXBvcnRhciwgZW0gcmF6w6NvIGRlIHF1YWxxdWVyIG9mZW5zYSBhIGRpcmVpdG9zIGF1dG9yYWlzIG91CmRpcmVpdG9zIGRlIHZveiBvdSBpbWFnZW0sIHByaW5jaXBhbG1lbnRlIG5vIHF1ZSBkaXogcmVzcGVpdG8gYSBwbMOhZ2lvIGUgdmlvbGHDp8O1ZXMgZGUgZGlyZWl0b3M7CgooNSkgQUZJUk1BIHF1ZSBjb25oZWNlIGEgUG9sw610aWNhIEluc3RpdHVjaW9uYWwgZGUgQWNlc3NvIEFiZXJ0byBkYSBGSU9DUlVaIC0gRlVOREHDh8ODTwpPU1dBTERPIENSVVogZSBhcyBkaXJldHJpemVzIHBhcmEgbyBmdW5jaW9uYW1lbnRvIGRvIHJlcG9zaXTDs3JpbyBpbnN0aXR1Y2lvbmFsIEFSQ0EuCgpBIFBvbMOtdGljYSBJbnN0aXR1Y2lvbmFsIGRlIEFjZXNzbyBBYmVydG8gZGEgRklPQ1JVWiAtIEZVTkRBw4fDg08gT1NXQUxETyBDUlVaIHJlc2VydmEKZXhjbHVzaXZhbWVudGUgYW8gQVVUT1Igb3MgZGlyZWl0b3MgbW9yYWlzIGUgb3MgdXNvcyBjb21lcmNpYWlzIHNvYnJlIGFzIG9icmFzIGRlIHN1YSBhdXRvcmlhCmUvb3UgdGl0dWxhcmlkYWRlLCBzZW5kbyBvcyB0ZXJjZWlyb3MgdXN1w6FyaW9zIHJlc3BvbnPDoXZlaXMgcGVsYSBhdHJpYnVpw6fDo28gZGUgYXV0b3JpYSBlIG1hbnV0ZW7Dp8OjbwpkYSBpbnRlZ3JpZGFkZSBkYSBPQlJBIGVtIHF1YWxxdWVyIHV0aWxpemHDp8Ojby4KCkEgUG9sw610aWNhIEluc3RpdHVjaW9uYWwgZGUgQWNlc3NvIEFiZXJ0byBkYSBGSU9DUlVaIC0gRlVOREHDh8ODTyBPU1dBTERPIENSVVoKcmVzcGVpdGEgb3MgY29udHJhdG9zIGUgYWNvcmRvcyBwcmVleGlzdGVudGVzIGRvcyBBdXRvcmVzIGNvbSB0ZXJjZWlyb3MsIGNhYmVuZG8gYW9zIEF1dG9yZXMKaW5mb3JtYXIgw6AgSW5zdGl0dWnDp8OjbyBhcyBjb25kacOnw7VlcyBlIG91dHJhcyByZXN0cmnDp8O1ZXMgaW1wb3N0YXMgcG9yIGVzdGVzIGluc3RydW1lbnRvcy4KRepositório 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| dc.title.en_US.fl_str_mv |
Synthesis and Biological Activities of Camphor Hydrazone and Imine Derivatives |
| title |
Synthesis and Biological Activities of Camphor Hydrazone and Imine Derivatives |
| spellingShingle |
Synthesis and Biological Activities of Camphor Hydrazone and Imine Derivatives Silva, Emerson T. da Camphor Hydrazones Imines Sonochemistry Tuberculosis |
| title_short |
Synthesis and Biological Activities of Camphor Hydrazone and Imine Derivatives |
| title_full |
Synthesis and Biological Activities of Camphor Hydrazone and Imine Derivatives |
| title_fullStr |
Synthesis and Biological Activities of Camphor Hydrazone and Imine Derivatives |
| title_full_unstemmed |
Synthesis and Biological Activities of Camphor Hydrazone and Imine Derivatives |
| title_sort |
Synthesis and Biological Activities of Camphor Hydrazone and Imine Derivatives |
| author |
Silva, Emerson T. da |
| author_facet |
Silva, Emerson T. da Araújo, Adriele da Silva Moraes, Adriana M. Souza, Leidiane A. de Lourenço, Maria Cristina Silva Souza, Marcus V. N. de Wardell, James L. Wardell, Solange M. S. V. |
| author_role |
author |
| author2 |
Araújo, Adriele da Silva Moraes, Adriana M. Souza, Leidiane A. de Lourenço, Maria Cristina Silva Souza, Marcus V. N. de Wardell, James L. Wardell, Solange M. S. V. |
| author2_role |
author author author author author author author |
| dc.contributor.author.fl_str_mv |
Silva, Emerson T. da Araújo, Adriele da Silva Moraes, Adriana M. Souza, Leidiane A. de Lourenço, Maria Cristina Silva Souza, Marcus V. N. de Wardell, James L. Wardell, Solange M. S. V. |
| dc.subject.en.en_US.fl_str_mv |
Camphor Hydrazones Imines Sonochemistry Tuberculosis |
| topic |
Camphor Hydrazones Imines Sonochemistry Tuberculosis |
| description |
The authors would like to acknowledge CNPq and Fiocruz for financial and infrastructure assistance. |
| publishDate |
2016 |
| dc.date.issued.fl_str_mv |
2016 |
| dc.date.accessioned.fl_str_mv |
2023-10-04T23:21:51Z |
| dc.date.available.fl_str_mv |
2023-10-04T23:21:51Z |
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info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/article |
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article |
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publishedVersion |
| dc.identifier.citation.fl_str_mv |
SILVA, Emerson T. da et al. Synthesis and Biological Activities of Camphor Hydrazone and Imine Derivatives. Scientia Pharmaceutica, v. 84, n. 3, p. 467-483, Oct. 2016. |
| dc.identifier.uri.fl_str_mv |
https://www.arca.fiocruz.br/handle/icict/60703 |
| dc.identifier.issn.en_US.fl_str_mv |
0036-8709 |
| dc.identifier.doi.none.fl_str_mv |
10.3390/scipharm84030467 |
| dc.identifier.eissn.none.fl_str_mv |
2218-0532 |
| identifier_str_mv |
SILVA, Emerson T. da et al. Synthesis and Biological Activities of Camphor Hydrazone and Imine Derivatives. Scientia Pharmaceutica, v. 84, n. 3, p. 467-483, Oct. 2016. 0036-8709 10.3390/scipharm84030467 2218-0532 |
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https://www.arca.fiocruz.br/handle/icict/60703 |
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eng |
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eng |
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info:eu-repo/semantics/openAccess |
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openAccess |
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Österreichische Apotheker-Verlagsgesellschaft |
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Österreichische Apotheker-Verlagsgesellschaft |
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reponame:Repositório Institucional da FIOCRUZ (ARCA) instname:Fundação Oswaldo Cruz (FIOCRUZ) instacron:FIOCRUZ |
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