Molecular structure studies on allyl sulfonamides: synthesis, theoretical treatment and evaluation of biological activity

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dc.creatorAnderson Silva Rabello
dc.creatorMayura M. M. Rubinger
dc.creatorRafael A. C. Souza
dc.creatorSilvana Guilardi
dc.creatorGuilherme Ferreira de Lima
dc.creatorEder Tavares
dc.creatorÉdipo P. Zanon
dc.creatorGiovanna R. N. Silva
dc.creatorLaércio Zambolim
dc.creatorJavier Ellena
dc.date.accessioned2023-10-04T19:21:54Z
dc.date.accessioned2025-09-08T23:11:36Z
dc.date.available2023-10-04T19:21:54Z
dc.date.issued2021
dc.description.sponsorshipCNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico
dc.description.sponsorshipFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas Gerais
dc.description.sponsorshipCAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
dc.format.mimetypepdf
dc.identifier.doihttps://dx.doi.org/10.21577/0103-5053.20210094
dc.identifier.issn1678-4790
dc.identifier.urihttps://hdl.handle.net/1843/59140
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofJournal of the Brazilian Chemical Society
dc.rightsAcesso Aberto
dc.subjectSulfonamidas
dc.subjectCristalografia por raios X
dc.subjectEstrutura molecular
dc.subjectBotrytis cinerea
dc.subject.otherSulfonamides
dc.subject.otherX-ray crystallography
dc.subject.otherHirshfeld surface
dc.subject.otherFrontier molecular orbitals
dc.subject.otherBotrytis cinerea
dc.titleMolecular structure studies on allyl sulfonamides: synthesis, theoretical treatment and evaluation of biological activity
dc.title.alternativeEstudos de estrutura molecular em alil sulfonamidas: síntese, tratamento teórico e avaliação da atividade biológica
dc.typeArtigo de periódico
local.citation.epage2046
local.citation.issue11
local.citation.spage2033
local.citation.volume32
local.description.resumoTwo 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.
local.identifier.orcidhttps://orcid.org/0000-0001-6947-1845
local.identifier.orcidhttps://orcid.org/0000-0002-7080-4552
local.identifier.orcidhttps://orcid.org/0000-0002-0311-3831
local.identifier.orcidhttps://orcid.org/0000-0001-5228-4912
local.identifier.orcidhttps://orcid.org/0000-0002-0676-3098
local.publisher.countryBrasil
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://jbcs.sbq.org.br/default.asp?ed=318

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