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Proceeding Paper

Structural Analogues of Thyronamines: Some Aspects of the Structure and Bioactivity of 4-[4-(2-Aminoetoxy)benzyl]aniline †

by
Alexander B. Eresko
1,*,
Elena V. Raksha
1,
Dmitry A. Filimonov
2,
Nadezhda N. Trubnikova
2,
Irina A. Kisilenko
2 and
Dorota M. Chudoba
1
1
Frank Laboratory of Neutron Physics, Joint Institute for Nuclear Research, Dubna 141980, Russia
2
Federal State Budgetary Institution “V.K. Gusak Institute of Emergency and Reconstructive Surgery” of the Ministry of Health of the Russian Federation, Donetsk 283045, Russia
*
Author to whom correspondence should be addressed.
†
Presented at the 28th International Electronic Conference on Synthetic Organic Chemistry (ECSOC-28), 15–30 November 2024; Available online: https://sciforum.net/event/ecsoc-28.
Chem. Proc. 2024, 16(1), 22; https://doi.org/10.3390/ecsoc-28-20165
Published: 14 November 2024
(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)
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Abstract

Molecular modelling of the structure and evaluation of the chemical shifts of 1H and 13C nuclei were performed for the 4-[4-(2-aminoethoxy)benzyl]aniline, which is a structural analogue of thyronamines. The intramolecular dynamics of the key structural fragments of 4-[4-(2-aminoethoxy)benzyl]aniline were studied by the PM6-DH2 method as well as at the B3LYP/6-31G(d,p) level of theory. Nonspecific solvation with dimethyl sulfoxide was taken into account within the polarized continuum model. Specific solvation by one and two DMSO molecules was considered within supermolecule approximation. Chemical shifts of the 1H and 13C nuclei were estimated for the most stable conformer of 4-[4-(2-aminoethoxy)benzyl]aniline as well as for its solvates with DMSO. Calculated chemical shifts of the 1H and 13C nuclei are in good agreement with the experimental ones obtained for 4-[4-(2-aminoethoxy)benzyl]aniline in DMSO-d6 solution. Some aspects of the bioactivity of 4-[4-(2-aminoethoxy)benzyl]aniline are discussed.
Keywords: thyronamines; intramolecular dynamics; conformers; DFT calculations; NMR spectroscopy; chemical shift; antioxidant effects thyronamines; intramolecular dynamics; conformers; DFT calculations; NMR spectroscopy; chemical shift; antioxidant effects

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MDPI and ACS Style

Eresko, A.B.; Raksha, E.V.; Filimonov, D.A.; Trubnikova, N.N.; Kisilenko, I.A.; Chudoba, D.M. Structural Analogues of Thyronamines: Some Aspects of the Structure and Bioactivity of 4-[4-(2-Aminoetoxy)benzyl]aniline. Chem. Proc. 2024, 16, 22. https://doi.org/10.3390/ecsoc-28-20165

AMA Style

Eresko AB, Raksha EV, Filimonov DA, Trubnikova NN, Kisilenko IA, Chudoba DM. Structural Analogues of Thyronamines: Some Aspects of the Structure and Bioactivity of 4-[4-(2-Aminoetoxy)benzyl]aniline. Chemistry Proceedings. 2024; 16(1):22. https://doi.org/10.3390/ecsoc-28-20165

Chicago/Turabian Style

Eresko, Alexander B., Elena V. Raksha, Dmitry A. Filimonov, Nadezhda N. Trubnikova, Irina A. Kisilenko, and Dorota M. Chudoba. 2024. "Structural Analogues of Thyronamines: Some Aspects of the Structure and Bioactivity of 4-[4-(2-Aminoetoxy)benzyl]aniline" Chemistry Proceedings 16, no. 1: 22. https://doi.org/10.3390/ecsoc-28-20165

APA Style

Eresko, A. B., Raksha, E. V., Filimonov, D. A., Trubnikova, N. N., Kisilenko, I. A., & Chudoba, D. M. (2024). Structural Analogues of Thyronamines: Some Aspects of the Structure and Bioactivity of 4-[4-(2-Aminoetoxy)benzyl]aniline. Chemistry Proceedings, 16(1), 22. https://doi.org/10.3390/ecsoc-28-20165

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