Structural Analogues of Thyronamines: Some Aspects of the Structure and Bioactivity of 4-[4-(2-Aminoetoxy)benzyl]aniline
Molecular modelling of the structure and evaluation of the chemical shifts of <sup>1</sup>H and <sup>13</sup>C 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 f...
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| author | Alexander B. Eresko Elena V. Raksha Dmitry A. Filimonov Nadezhda N. Trubnikova Irina A. Kisilenko Dorota M. Chudoba |
| author_facet | Alexander B. Eresko Elena V. Raksha Dmitry A. Filimonov Nadezhda N. Trubnikova Irina A. Kisilenko Dorota M. Chudoba |
| author_sort | Alexander B. Eresko |
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| description | Molecular modelling of the structure and evaluation of the chemical shifts of <sup>1</sup>H and <sup>13</sup>C 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 <sup>1</sup>H and <sup>13</sup>C 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 <sup>1</sup>H and <sup>13</sup>C nuclei are in good agreement with the experimental ones obtained for 4-[4-(2-aminoethoxy)benzyl]aniline in DMSO-d<sub>6</sub> solution. Some aspects of the bioactivity of 4-[4-(2-aminoethoxy)benzyl]aniline are discussed. |
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| issn | 2673-4583 |
| language | English |
| publishDate | 2024-11-01 |
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| spelling | doaj-art-e79ae80f7f1a42528bdf546fe916bbf22025-08-20T02:24:42ZengMDPI AGChemistry Proceedings2673-45832024-11-011612210.3390/ecsoc-28-20165Structural Analogues of Thyronamines: Some Aspects of the Structure and Bioactivity of 4-[4-(2-Aminoetoxy)benzyl]anilineAlexander B. Eresko0Elena V. Raksha1Dmitry A. Filimonov2Nadezhda N. Trubnikova3Irina A. Kisilenko4Dorota M. Chudoba5Frank Laboratory of Neutron Physics, Joint Institute for Nuclear Research, Dubna 141980, RussiaFrank Laboratory of Neutron Physics, Joint Institute for Nuclear Research, Dubna 141980, RussiaFederal State Budgetary Institution “V.K. Gusak Institute of Emergency and Reconstructive Surgery” of the Ministry of Health of the Russian Federation, Donetsk 283045, RussiaFederal State Budgetary Institution “V.K. Gusak Institute of Emergency and Reconstructive Surgery” of the Ministry of Health of the Russian Federation, Donetsk 283045, RussiaFederal State Budgetary Institution “V.K. Gusak Institute of Emergency and Reconstructive Surgery” of the Ministry of Health of the Russian Federation, Donetsk 283045, RussiaFrank Laboratory of Neutron Physics, Joint Institute for Nuclear Research, Dubna 141980, RussiaMolecular modelling of the structure and evaluation of the chemical shifts of <sup>1</sup>H and <sup>13</sup>C 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 <sup>1</sup>H and <sup>13</sup>C 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 <sup>1</sup>H and <sup>13</sup>C nuclei are in good agreement with the experimental ones obtained for 4-[4-(2-aminoethoxy)benzyl]aniline in DMSO-d<sub>6</sub> solution. Some aspects of the bioactivity of 4-[4-(2-aminoethoxy)benzyl]aniline are discussed.https://www.mdpi.com/2673-4583/16/1/22thyronaminesintramolecular dynamicsconformersDFT calculationsNMR spectroscopychemical shift |
| spellingShingle | Alexander B. Eresko Elena V. Raksha Dmitry A. Filimonov Nadezhda N. Trubnikova Irina A. Kisilenko Dorota M. Chudoba Structural Analogues of Thyronamines: Some Aspects of the Structure and Bioactivity of 4-[4-(2-Aminoetoxy)benzyl]aniline Chemistry Proceedings thyronamines intramolecular dynamics conformers DFT calculations NMR spectroscopy chemical shift |
| title | Structural Analogues of Thyronamines: Some Aspects of the Structure and Bioactivity of 4-[4-(2-Aminoetoxy)benzyl]aniline |
| title_full | Structural Analogues of Thyronamines: Some Aspects of the Structure and Bioactivity of 4-[4-(2-Aminoetoxy)benzyl]aniline |
| title_fullStr | Structural Analogues of Thyronamines: Some Aspects of the Structure and Bioactivity of 4-[4-(2-Aminoetoxy)benzyl]aniline |
| title_full_unstemmed | Structural Analogues of Thyronamines: Some Aspects of the Structure and Bioactivity of 4-[4-(2-Aminoetoxy)benzyl]aniline |
| title_short | Structural Analogues of Thyronamines: Some Aspects of the Structure and Bioactivity of 4-[4-(2-Aminoetoxy)benzyl]aniline |
| title_sort | structural analogues of thyronamines some aspects of the structure and bioactivity of 4 4 2 aminoetoxy benzyl aniline |
| topic | thyronamines intramolecular dynamics conformers DFT calculations NMR spectroscopy chemical shift |
| url | https://www.mdpi.com/2673-4583/16/1/22 |
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