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Unexpected synthesis and crystal structure of N-{2-[2-(2-acetylethenyl)phenoxy]ethyl}-N-ethenyl-4-methylbenzenesulfonamide
The title compound, C(21)H(23)NO(4)S, obtained by alkaline treatment of 1,5-bis(1-phenoxy)-3-azapentane at moderate heating, is a N-tosylated secondary vinylamine. An intramolecular S=O⋯H—C hydrogen bond generates a 13-membered ring. The benzalacetone moiety adopts a trans conformation with re...
| Autores principales: | , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
International Union of Crystallography
2020
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7784650/ https://www.ncbi.nlm.nih.gov/pubmed/33520267 http://dx.doi.org/10.1107/S2056989020015194 |
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| author | Temesgen, Ayalew W. Luong, Minh Duc Truong, Hong Hieu Nguyen, Van Tuyen Dang, Thi Tuyet Anh Le, Tuan Anh Tskhovrebov, Alexander G. Khrustalev, Victor N. |
| author_facet | Temesgen, Ayalew W. Luong, Minh Duc Truong, Hong Hieu Nguyen, Van Tuyen Dang, Thi Tuyet Anh Le, Tuan Anh Tskhovrebov, Alexander G. Khrustalev, Victor N. |
| author_sort | Temesgen, Ayalew W. |
| collection | PubMed |
| description | The title compound, C(21)H(23)NO(4)S, obtained by alkaline treatment of 1,5-bis(1-phenoxy)-3-azapentane at moderate heating, is a N-tosylated secondary vinylamine. An intramolecular S=O⋯H—C hydrogen bond generates a 13-membered ring. The benzalacetone moiety adopts a trans conformation with respect to the C=C double bond, which is slightly longer than usual due to the conjugation with a neighbouring acetyl group. Theoretical predictions of potential biological activities were performed, suggesting that the title compound can inhibit gluconate 2-dehydrogenase (85% probability), as well as to act as a mucomembranous protector (73%). |
| format | Online Article Text |
| id | pubmed-7784650 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2020 |
| publisher | International Union of Crystallography |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-77846502021-01-29 Unexpected synthesis and crystal structure of N-{2-[2-(2-acetylethenyl)phenoxy]ethyl}-N-ethenyl-4-methylbenzenesulfonamide Temesgen, Ayalew W. Luong, Minh Duc Truong, Hong Hieu Nguyen, Van Tuyen Dang, Thi Tuyet Anh Le, Tuan Anh Tskhovrebov, Alexander G. Khrustalev, Victor N. Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(21)H(23)NO(4)S, obtained by alkaline treatment of 1,5-bis(1-phenoxy)-3-azapentane at moderate heating, is a N-tosylated secondary vinylamine. An intramolecular S=O⋯H—C hydrogen bond generates a 13-membered ring. The benzalacetone moiety adopts a trans conformation with respect to the C=C double bond, which is slightly longer than usual due to the conjugation with a neighbouring acetyl group. Theoretical predictions of potential biological activities were performed, suggesting that the title compound can inhibit gluconate 2-dehydrogenase (85% probability), as well as to act as a mucomembranous protector (73%). International Union of Crystallography 2020-11-20 /pmc/articles/PMC7784650/ /pubmed/33520267 http://dx.doi.org/10.1107/S2056989020015194 Text en © Temesgen et al. 2020 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/ |
| spellingShingle | Research Communications Temesgen, Ayalew W. Luong, Minh Duc Truong, Hong Hieu Nguyen, Van Tuyen Dang, Thi Tuyet Anh Le, Tuan Anh Tskhovrebov, Alexander G. Khrustalev, Victor N. Unexpected synthesis and crystal structure of N-{2-[2-(2-acetylethenyl)phenoxy]ethyl}-N-ethenyl-4-methylbenzenesulfonamide |
| title | Unexpected synthesis and crystal structure of N-{2-[2-(2-acetylethenyl)phenoxy]ethyl}-N-ethenyl-4-methylbenzenesulfonamide |
| title_full | Unexpected synthesis and crystal structure of N-{2-[2-(2-acetylethenyl)phenoxy]ethyl}-N-ethenyl-4-methylbenzenesulfonamide |
| title_fullStr | Unexpected synthesis and crystal structure of N-{2-[2-(2-acetylethenyl)phenoxy]ethyl}-N-ethenyl-4-methylbenzenesulfonamide |
| title_full_unstemmed | Unexpected synthesis and crystal structure of N-{2-[2-(2-acetylethenyl)phenoxy]ethyl}-N-ethenyl-4-methylbenzenesulfonamide |
| title_short | Unexpected synthesis and crystal structure of N-{2-[2-(2-acetylethenyl)phenoxy]ethyl}-N-ethenyl-4-methylbenzenesulfonamide |
| title_sort | unexpected synthesis and crystal structure of n-{2-[2-(2-acetylethenyl)phenoxy]ethyl}-n-ethenyl-4-methylbenzenesulfonamide |
| topic | Research Communications |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7784650/ https://www.ncbi.nlm.nih.gov/pubmed/33520267 http://dx.doi.org/10.1107/S2056989020015194 |
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