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Article

2-Chloro-4,6-bis{(E)-3-methoxy-4-[(4-methoxybenzyl)oxy]styryl}pyrimidine: Synthesis, Spectroscopic and Computational Evaluation

1
Centro de Química de Coimbra (CQC), Departamento de Química, Universidade de Coimbra, Rua Larga, 3004-545 Coimbra, Portugal
2
Departamento de Química Orgânica, Instituto de Química, Universidade Federal Rural do Rio de Janeiro, Seropédica 23890-000, Brazil
3
Instituto Federal de Educação, Ciência e Tecnologia do Rio de Janeiro, Campus São Gonçalo, Rua José Augusto Pereira dos Santos, São Gonçalo 24425-004, Brazil
4
Departamento de Química Orgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, Centro de Tecnologia, Bloco A, Cidade Universitária, Rio de Janeiro 21941-909, Brazil
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Departamento de Microbiologia e Imunologia Veterinária, Instituto de Veterinária, Universidade Federal Rural do Rio de Janeiro, Seropédica 23890-000, Brazil
*
Author to whom correspondence should be addressed.
This work is dedicated to the memory of the honorable Brazilian scientist, teacher, friend and human being Vitor Sueth-Santiago (1987–2021). A victim from COVID-19.
Academic Editor: Giovanni Ribaudo
Molbank 2021, 2021(3), M1276; https://doi.org/10.3390/M1276
Received: 31 July 2021 / Revised: 25 August 2021 / Accepted: 29 August 2021 / Published: 7 September 2021
(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)
A novel curcumin analog namely 2-chloro-4,6-bis{(E)-3-methoxy-4-[(4-methoxybenzyl)oxy]-styryl}pyrimidine (compound 7) was synthesized by three-step reaction. The condensation reaction of protected vanillin with 2-chloro-4,6-dimethylpyrimidine (6) was the most efficient step, resulting in a total yield of 72%. The characterization of compound 7 was performed by 1H and 13C nuclear magnetic resonance (NMR), as well as high-resolution mass spectrometry. The experimental spectrometric data were compared with the theoretical spectra obtained by the density functional theory (DFT) method, showing a perfect match between them. UV-visible spectroscopy and steady-state fluorescence emission studies were performed for compound 7 in solvents of different polarities and the results were correlated with DFT calculations. Compound 7 showed a solvatochromism effect presenting higher molar extinction coefficient (log ε = 4.57) and fluorescence quantum yield (ϕ = 0.38) in toluene than in acetonitrile or methanol. The simulation of both frontier molecular orbitals (FMOs) and molecular electrostatic potential (MEP) suggested that the experimental spectra profile in toluene was not interfered by a possible charge transfer. These results are an indication of a low probability of compound 7 in reacting with unsaturated phospholipids in future applications as a fluorescent dye in biological systems. View Full-Text
Keywords: curcumin analog; organic synthesis; photophysical properties; steady-state fluorescence; DFT calculation curcumin analog; organic synthesis; photophysical properties; steady-state fluorescence; DFT calculation
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MDPI and ACS Style

Chaves, O.A.; Sueth-Santiago, V.; Pinto, D.C.d.A.; Netto-Ferreira, J.C.; Decote-Ricardo, D.; Lima, M.E.F.d. 2-Chloro-4,6-bis{(E)-3-methoxy-4-[(4-methoxybenzyl)oxy]styryl}pyrimidine: Synthesis, Spectroscopic and Computational Evaluation. Molbank 2021, 2021, M1276. https://doi.org/10.3390/M1276

AMA Style

Chaves OA, Sueth-Santiago V, Pinto DCdA, Netto-Ferreira JC, Decote-Ricardo D, Lima MEFd. 2-Chloro-4,6-bis{(E)-3-methoxy-4-[(4-methoxybenzyl)oxy]styryl}pyrimidine: Synthesis, Spectroscopic and Computational Evaluation. Molbank. 2021; 2021(3):M1276. https://doi.org/10.3390/M1276

Chicago/Turabian Style

Chaves, Otávio A., Vitor Sueth-Santiago, Douglas C.d.A. Pinto, José C. Netto-Ferreira, Debora Decote-Ricardo, and Marco E.F.d. Lima 2021. "2-Chloro-4,6-bis{(E)-3-methoxy-4-[(4-methoxybenzyl)oxy]styryl}pyrimidine: Synthesis, Spectroscopic and Computational Evaluation" Molbank 2021, no. 3: M1276. https://doi.org/10.3390/M1276

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