Molecular structure studies on Allyl sulfonamides: synthesis, theoretical treatment and evaluation of biological activity
| Autor: | Javier Ellena, Mayura M. M. Rubinger, Anderson S Rabello, Guilherme Ferreira de Lima, Rafael A.C. Souza, Silvana Guilardi, Eder do Couto Tavares, Giovanna R. N Silva, Édipo P Zanon, Laércio Zambolim |
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| Rok vydání: | 2021 |
| Předmět: |
Chemistry
Hirshfeld surface frontier molecular orbitals General Chemistry Crystal structure Antibonding molecular orbital Medicinal chemistry Adduct chemistry.chemical_compound Botrytis cinerea sulfonamides X-ray crystallography Molecule Molecular orbital Density functional theory Acrylonitrile ESTRUTURA MOLECULAR (QUÍMICA TEÓRICA) |
| Zdroj: | Repositório Institucional da USP (Biblioteca Digital da Produção Intelectual) Universidade de São Paulo (USP) instacron:USP Journal of the Brazilian Chemical Society, Volume: 32, Issue: 11, Pages: 2033-2046, Published: 25 OCT 2021 Journal of the Brazilian Chemical Society v.32 n.11 2021 Journal of the Brazilian Chemical Society Sociedade Brasileira de Química (SBQ) instacron:SBQ |
| Popis: | Two 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. |
| Databáze: | OpenAIRE |
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