Molecular structure studies on allyl sulfonamides: synthesis, theoretical treatment and evaluation of biological activity
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2021 |
| Outros Autores: | , , , , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Institucional da UFMG |
| Texto Completo: | https://dx.doi.org/10.21577/0103-5053.20210094 http://hdl.handle.net/1843/59140 https://orcid.org/0000-0001-6947-1845 https://orcid.org/0000-0002-7080-4552 https://orcid.org/0000-0002-0311-3831 https://orcid.org/0000-0001-5228-4912 https://orcid.org/0000-0002-0676-3098 |
Resumo: | CNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico |
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2023-10-04T19:21:54Z2023-10-04T19:21:54Z2021321120332046https://dx.doi.org/10.21577/0103-5053.202100941678-4790http://hdl.handle.net/1843/59140https://orcid.org/0000-0001-6947-1845https://orcid.org/0000-0002-7080-4552https://orcid.org/0000-0002-0311-3831https://orcid.org/0000-0001-5228-4912https://orcid.org/0000-0002-0676-3098CNPq - Conselho Nacional de Desenvolvimento Científico e TecnológicoFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas GeraisCAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível SuperiorTwo series of allyl sulfonamides, prepared from Morita-Baylis-Hillman adducts and primary aromatic sulfonamides, were fully characterized. The Z configuration for the products derived from 2-[hydroxy(phenyl)methyl]acrylonitrile (1) and E configuration for those derived from methyl 2-[hydroxy(phenyl)methyl]acrylate (2) were confirmed by X-ray diffraction for one compound of each series (1e, 2f). Density functional theory calculations for all allyl sulfonamides agreed with the X-ray crystallographic data. X-ray diffraction studies indicate that these compounds form dimers in their crystal structures. Fingerprint plots show that compound 1e is stabilized by H⋯H, C⋯H/H⋯C, O⋯H/H⋯O and N⋯H/H⋯N interactions, while the compound 2f has no N⋯H/H⋯N contacts. Hirshfeld surface analyses were performed to gain insight into the behavior of these interactions. Calculated frontier orbitals showed that their highest occupied and lowest unoccupied molecular orbitals are antibonding orbitals. The allyl sulfonamides 1e and 2f are among the most active compounds in each series, inhibiting approximately 60% of the mycelial growth of Botrytis cinerea at 3 mmol L-1.engUniversidade Federal de Minas GeraisUFMGBrasilICX - DEPARTAMENTO DE QUÍMICAJournal of the Brazilian Chemical SocietySulfonamidasCristalografia por raios XEstrutura molecularBotrytis cinereaSulfonamidesX-ray crystallographyHirshfeld surfaceFrontier molecular orbitalsBotrytis cinereaMolecular structure studies on allyl sulfonamides: synthesis, theoretical treatment and evaluation of biological activityEstudos de estrutura molecular em alil sulfonamidas: síntese, tratamento teórico e avaliação da atividade biológicainfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttps://jbcs.sbq.org.br/default.asp?ed=318Anderson Silva RabelloMayura M. M. RubingerRafael A. C. SouzaSilvana GuilardiGuilherme Ferreira de LimaEder TavaresÉdipo P. ZanonGiovanna R. N. SilvaLaércio ZambolimJavier Ellenaapplication/pdfinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFMGinstname:Universidade Federal de Minas Gerais (UFMG)instacron:UFMGLICENSELicense.txtLicense.txttext/plain; charset=utf-82042https://repositorio.ufmg.br/bitstream/1843/59140/1/License.txtfa505098d172de0bc8864fc1287ffe22MD51ORIGINALMolecular structure studies on allyl sulfonamides: synthesis, theoretical treatment and evaluation of biological activityMolecular structure studies on allyl sulfonamides: synthesis, theoretical treatment and evaluation of biological activityapplication/pdf4725286https://repositorio.ufmg.br/bitstream/1843/59140/2/Molecular%20structure%20studies%20on%20allyl%20sulfonamides%3a%20synthesis%2c%20theoretical%20treatment%20and%20evaluation%20of%20biological%20activity4f1a984a27c655611bd852f0fb49378fMD521843/591402023-10-04 16:22:11.054oai:repositorio.ufmg.br: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Repositório de PublicaçõesPUBhttps://repositorio.ufmg.br/oaiopendoar:2023-10-04T19:22:11Repositório Institucional da UFMG - Universidade Federal de Minas Gerais (UFMG)false |
| dc.title.pt_BR.fl_str_mv |
Molecular structure studies on allyl sulfonamides: synthesis, theoretical treatment and evaluation of biological activity |
| dc.title.alternative.pt_BR.fl_str_mv |
Estudos de estrutura molecular em alil sulfonamidas: síntese, tratamento teórico e avaliação da atividade biológica |
| title |
Molecular structure studies on allyl sulfonamides: synthesis, theoretical treatment and evaluation of biological activity |
| spellingShingle |
Molecular structure studies on allyl sulfonamides: synthesis, theoretical treatment and evaluation of biological activity Anderson Silva Rabello Sulfonamides X-ray crystallography Hirshfeld surface Frontier molecular orbitals Botrytis cinerea Sulfonamidas Cristalografia por raios X Estrutura molecular Botrytis cinerea |
| title_short |
Molecular structure studies on allyl sulfonamides: synthesis, theoretical treatment and evaluation of biological activity |
| title_full |
Molecular structure studies on allyl sulfonamides: synthesis, theoretical treatment and evaluation of biological activity |
| title_fullStr |
Molecular structure studies on allyl sulfonamides: synthesis, theoretical treatment and evaluation of biological activity |
| title_full_unstemmed |
Molecular structure studies on allyl sulfonamides: synthesis, theoretical treatment and evaluation of biological activity |
| title_sort |
Molecular structure studies on allyl sulfonamides: synthesis, theoretical treatment and evaluation of biological activity |
| author |
Anderson Silva Rabello |
| author_facet |
Anderson Silva Rabello Mayura M. M. Rubinger Rafael A. C. Souza Silvana Guilardi Guilherme Ferreira de Lima Eder Tavares Édipo P. Zanon Giovanna R. N. Silva Laércio Zambolim Javier Ellena |
| author_role |
author |
| author2 |
Mayura M. M. Rubinger Rafael A. C. Souza Silvana Guilardi Guilherme Ferreira de Lima Eder Tavares Édipo P. Zanon Giovanna R. N. Silva Laércio Zambolim Javier Ellena |
| author2_role |
author author author author author author author author author |
| dc.contributor.author.fl_str_mv |
Anderson Silva Rabello Mayura M. M. Rubinger Rafael A. C. Souza Silvana Guilardi Guilherme Ferreira de Lima Eder Tavares Édipo P. Zanon Giovanna R. N. Silva Laércio Zambolim Javier Ellena |
| dc.subject.por.fl_str_mv |
Sulfonamides X-ray crystallography Hirshfeld surface Frontier molecular orbitals Botrytis cinerea |
| topic |
Sulfonamides X-ray crystallography Hirshfeld surface Frontier molecular orbitals Botrytis cinerea Sulfonamidas Cristalografia por raios X Estrutura molecular Botrytis cinerea |
| dc.subject.other.pt_BR.fl_str_mv |
Sulfonamidas Cristalografia por raios X Estrutura molecular Botrytis cinerea |
| description |
CNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico |
| publishDate |
2021 |
| dc.date.issued.fl_str_mv |
2021 |
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2023-10-04T19:21:54Z |
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2023-10-04T19:21:54Z |
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info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/article |
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http://hdl.handle.net/1843/59140 |
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https://dx.doi.org/10.21577/0103-5053.20210094 |
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1678-4790 |
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https://orcid.org/0000-0001-6947-1845 https://orcid.org/0000-0002-7080-4552 https://orcid.org/0000-0002-0311-3831 https://orcid.org/0000-0001-5228-4912 https://orcid.org/0000-0002-0676-3098 |
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1678-4790 |
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eng |
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eng |
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Journal of the Brazilian Chemical Society |
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info:eu-repo/semantics/openAccess |
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openAccess |
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Universidade Federal de Minas Gerais |
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UFMG |
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Brasil |
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ICX - DEPARTAMENTO DE QUÍMICA |
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Universidade Federal de Minas Gerais |
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