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10α-Hydroxy-13-{[4-(2-hydroxyphenyl)piperazin-1-yl]methyl}-4,9-dimethyl-3,8,15-trioxatetracyclo[10.3.0.0(2,4).0(7,9)]pentadecan-14-one
The title compound, C(25)H(34)N(2)O(6), was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylene-3,14-dioxatricyclo[9.3.0.0(2,4)]tetradec-7-en-13-one), which was isolated from the chloroform extract of the aerial parts of Anvillea radiata. The ten-membered ring adopts...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2012
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3344453/ https://www.ncbi.nlm.nih.gov/pubmed/22590215 http://dx.doi.org/10.1107/S1600536812013876 |
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author | Moumou, Mohamed Benharref, Ahmed El Ammari, Lahcen Adil, Mina Berraho, Moha |
author_facet | Moumou, Mohamed Benharref, Ahmed El Ammari, Lahcen Adil, Mina Berraho, Moha |
author_sort | Moumou, Mohamed |
collection | PubMed |
description | The title compound, C(25)H(34)N(2)O(6), was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylene-3,14-dioxatricyclo[9.3.0.0(2,4)]tetradec-7-en-13-one), which was isolated from the chloroform extract of the aerial parts of Anvillea radiata. The ten-membered ring adopts an approximate chair–chair conformation, while the piperazine ring displays a near regular chair conformation and the five-membered ring an envelope conformation with the C atom closest to the hydroxy group forming the flap. The molecular conformation is stabilized by an O—H⋯N hydrogen bond, which generates an S(7) loop, and the crystal structure features weak C—H⋯O interactions. |
format | Online Article Text |
id | pubmed-3344453 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-33444532012-05-15 10α-Hydroxy-13-{[4-(2-hydroxyphenyl)piperazin-1-yl]methyl}-4,9-dimethyl-3,8,15-trioxatetracyclo[10.3.0.0(2,4).0(7,9)]pentadecan-14-one Moumou, Mohamed Benharref, Ahmed El Ammari, Lahcen Adil, Mina Berraho, Moha Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(25)H(34)N(2)O(6), was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylene-3,14-dioxatricyclo[9.3.0.0(2,4)]tetradec-7-en-13-one), which was isolated from the chloroform extract of the aerial parts of Anvillea radiata. The ten-membered ring adopts an approximate chair–chair conformation, while the piperazine ring displays a near regular chair conformation and the five-membered ring an envelope conformation with the C atom closest to the hydroxy group forming the flap. The molecular conformation is stabilized by an O—H⋯N hydrogen bond, which generates an S(7) loop, and the crystal structure features weak C—H⋯O interactions. International Union of Crystallography 2012-04-06 /pmc/articles/PMC3344453/ /pubmed/22590215 http://dx.doi.org/10.1107/S1600536812013876 Text en © Moumou et al. 2012 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Organic Papers Moumou, Mohamed Benharref, Ahmed El Ammari, Lahcen Adil, Mina Berraho, Moha 10α-Hydroxy-13-{[4-(2-hydroxyphenyl)piperazin-1-yl]methyl}-4,9-dimethyl-3,8,15-trioxatetracyclo[10.3.0.0(2,4).0(7,9)]pentadecan-14-one |
title | 10α-Hydroxy-13-{[4-(2-hydroxyphenyl)piperazin-1-yl]methyl}-4,9-dimethyl-3,8,15-trioxatetracyclo[10.3.0.0(2,4).0(7,9)]pentadecan-14-one |
title_full | 10α-Hydroxy-13-{[4-(2-hydroxyphenyl)piperazin-1-yl]methyl}-4,9-dimethyl-3,8,15-trioxatetracyclo[10.3.0.0(2,4).0(7,9)]pentadecan-14-one |
title_fullStr | 10α-Hydroxy-13-{[4-(2-hydroxyphenyl)piperazin-1-yl]methyl}-4,9-dimethyl-3,8,15-trioxatetracyclo[10.3.0.0(2,4).0(7,9)]pentadecan-14-one |
title_full_unstemmed | 10α-Hydroxy-13-{[4-(2-hydroxyphenyl)piperazin-1-yl]methyl}-4,9-dimethyl-3,8,15-trioxatetracyclo[10.3.0.0(2,4).0(7,9)]pentadecan-14-one |
title_short | 10α-Hydroxy-13-{[4-(2-hydroxyphenyl)piperazin-1-yl]methyl}-4,9-dimethyl-3,8,15-trioxatetracyclo[10.3.0.0(2,4).0(7,9)]pentadecan-14-one |
title_sort | 10α-hydroxy-13-{[4-(2-hydroxyphenyl)piperazin-1-yl]methyl}-4,9-dimethyl-3,8,15-trioxatetracyclo[10.3.0.0(2,4).0(7,9)]pentadecan-14-one |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3344453/ https://www.ncbi.nlm.nih.gov/pubmed/22590215 http://dx.doi.org/10.1107/S1600536812013876 |
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