Computation and structural elucidation of compounds formed via epoxide alcoholysis

Alvarenga, Elson S.; Teixeira, Milena Galdino; Lopes, Dayane T.; Demuner, Antônio J.

doi:10.1002/mrc.4818

Cited by 10 publications

(12 citation statements)

References 20 publications

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“…The deshielding of H5 and H6 is strong evidence of the epoxide opening. Theoretical calculations for the stereochemistry assignment of these compounds were discussed in detail …”

Section: Resultsmentioning

confidence: 99%

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Herbicidal activity of isobenzofuranones and in silico identification of their enzyme target

Teixeira

Alvarenga

Lopes

et al. 2019

Pest Management Science

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BACKGROUND Given the weed resistance to various herbicides with different mechanisms of action, the search for new compounds that are more effective and exhibit low levels of impact to other species in nature has been imperative in the field of the agriculture. For this purpose, 16 phthalides, and furan‐2(5H)‐one were synthetized and evaluated for their effectiveness as herbicides in seeds of Sorghum bicolor (sorghum), Cucumis sativus (cucumber), and Allium cepa (onion). Furthermore, a preliminary in silico study was carried out to identify the enzyme target of the most active compounds. RESULTS In the assays with S. bicolor, the mixture rac‐(3aR,4R,5S,6S,7S,7aS)‐5,6‐dibromohexahydro‐4,7‐methanoisobenzofuran‐1(3H)‐one + rac‐(3aR,4R,5R,6R,7S,7aS)‐5,6‐dibromohexahydro‐4,7‐methanoisobenzofuran‐1(3H)‐one (15a + 15b) showed comparable inhibitory activity to (S)‐metolachlor, which was used as control herbicide at concentrations ranging from 50 μm to 1000 μm. The developments of the seeds evaluated were altered by all 17 compounds, either stimulating or inhibiting. The best results were presented by compounds 15a, and 15b, either in their pure form or as a mixture. CONCLUSION The results presented by 15a, and 15b were superior to the activity of the commercial herbicide (S)‐metolachlor in the assays with C. sativus, and A. cepa. The in silico study provides strong evidence that the most active compounds bind to strigolactones esterases D14 through the same binding site of (5R)‐5‐hydroxy‐3‐methylfuran‐2(5H)‐one (H3M), which is one of the strigolactones (SLs) cleavage products. © 2019 Society of Chemical Industry

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“…The deshielding of H5 and H6 is strong evidence of the epoxide opening. Theoretical calculations for the stereochemistry assignment of these compounds were discussed in detail …”

Section: Resultsmentioning

confidence: 99%

“…Theoretical calculations for the stereochemistry assignment of these compounds were discussed in detail. 50…”

Section: Synthesismentioning

confidence: 99%

Herbicidal activity of isobenzofuranones and in silico identification of their enzyme target

Teixeira

Alvarenga

Lopes

et al. 2019

Pest Management Science

Self Cite

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“…Theoretical calculations were performed at Density Functional Theory (DFT) level to confirm the structure of the lactam. This method has been used in several instances in the structure elucidation of organic compounds obtained from natural or synthetic sources (PINTO et al, 2022;ALVARENGA et al, 2019;OLIVEIRA et al, 2018;TEIXEIRA et al, 2016). The calculations were performed for three candidate structures, differentiated only by the position of the double bond (Figure 1).…”

Section: Resultsmentioning

confidence: 99%

Structural elucidation of a lactam isolated from Bunchosia glandulifera and antioxidant activity

Blank¹,

Demuner²,

Baía³

et al. 2023

PRW

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3,6-Diidropiridin-2(1H)-ona foi isolado do extrato das sementes de Bunchosia glandulifera e D-mannitol isolado do extrato da polpa. A elucidação estrutural da 3,6-diidropiridin-2(1H)-ona foi realizada empregando os métodos espectrométricos. Cálculos teóricos dos deslocamentos químicos de RMN de 1H e 13C para três estruturas candidatas foram realizados. Os deslocamentos químicos calculados foram comparados com os valores experimentais empregando o método estatístico DP4. A probabilidade de DP4 para carbono e hidrogênio foi de 100% para a estrutura candidata R1 (3,6-diidropiridin-2(1H)-ona), confirmando a estrutura proposta pela interpretação dos dados espectrométricos. Atividade antioxidante dos compostos isolados foi avaliada in vitro, usando o método ácido 2,2-azino-bis(3-etilbenzotiazolina-6-sulfônico) (ABTS), 2,2-difenil-1-picrilhidrazil (DPPH), redução do ferro (FRAP) e poder redutor.

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“…So far NMR has successfully identified novel molecules in multiple FBDD drug discovery experiments (39)(40)(41)(42)(43)(44). NMR can also be used in chemistry for the structural elucidation of a molecule (45)(46)(47). NMR can even be used in quality assessment for the food industry (48,49) and petroleum industry (50,51).…”

Section: The Application Of Nmr To Metabonomicsmentioning

confidence: 99%

1H Nuclear Magnetic Resonance: A Future Approach to the Metabolic Profiling of Psychedelics in Human Biofluids?

2021

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While psychedelics may have therapeutic potential for treating mental health disorders such as depression, further research is needed to better understand their biological effects and mechanisms of action when considering the development of future novel therapy approaches. Psychedelic research could potentially benefit from the integration of metabonomics by proton nuclear magnetic resonance (1H NMR) spectroscopy which is an analytical chemistry-based approach that can measure the breakdown of drugs into their metabolites and their metabolic consequences from various biofluids. We have performed a systematic review with the primary aim of exploring published literature where 1H NMR analysed psychedelic substances including psilocin, lysergic acid diethylamide (LSD), LSD derivatives, N,N-dimethyltryptamine (DMT), 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) and bufotenin. The second aim was to assess the benefits and limitations of 1H NMR spectroscopy-based metabolomics as a tool in psychedelic research and the final aim was to explore potential future directions. We found that the most current use of 1H NMR in psychedelic research has been for the structural elucidation and analytical characterisation of psychedelic molecules and that no papers used 1H NMR in the metabolic profiling of biofluids, thus exposing a current research gap and the underuse of 1H NMR. The efficacy of 1H NMR spectroscopy was also compared to mass spectrometry, where both metabonomics techniques have previously shown to be appropriate for biofluid analysis in other applications. Additionally, potential future directions for psychedelic research were identified as real-time NMR, in vivo1H nuclear magnetic resonance spectroscopy (MRS) and 1H NMR studies of the gut microbiome. Further psychedelic studies need to be conducted that incorporate the use of 1H NMR spectroscopy in the analysis of metabolites both in the peripheral biofluids and in vivo to determine whether it will be an effective future approach for clinical and naturalistic research.

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Computation and structural elucidation of compounds formed via epoxide alcoholysis

Cited by 10 publications

References 20 publications

Herbicidal activity of isobenzofuranones and in silico identification of their enzyme target

Herbicidal activity of isobenzofuranones and in silico identification of their enzyme target

Structural elucidation of a lactam isolated from Bunchosia glandulifera and antioxidant activity

1H Nuclear Magnetic Resonance: A Future Approach to the Metabolic Profiling of Psychedelics in Human Biofluids?

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