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12-{[4-(4-Bromophenyl)piperazin-1-yl]methyl}-9α-hydroxy-4,8-dimethyl-3,14-dioxatricyclo[9.3.0.0(2,4)]tetradec-7-en-13-one
The title compound, C(25)H(33)BrN(2)O(4), was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylen-3,14-dioxa-tricyclo[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 molecule is built up...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998562/ https://www.ncbi.nlm.nih.gov/pubmed/24826186 http://dx.doi.org/10.1107/S1600536814006473 |
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author | Loubidi, Mohamed Benharref, Ahmed El Ammari, Lahcen Saadi, Mohamed Berraho, Moha |
author_facet | Loubidi, Mohamed Benharref, Ahmed El Ammari, Lahcen Saadi, Mohamed Berraho, Moha |
author_sort | Loubidi, Mohamed |
collection | PubMed |
description | The title compound, C(25)H(33)BrN(2)O(4), was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylen-3,14-dioxa-tricyclo[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 molecule is built up from two fused five- and ten-membered rings with an additional epoxy ring system and a bromophenylpiperazine group as a substituent. The ten-membered ring adopts an approximate chair–chair–chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring shows an envelope conformation with the C atom closest to the hydroxy group forming the flap. An intramolecular O—H⋯N hydrogen bond stabilizes the molecular conformation. The crystal packing features C—H⋯O hydrogen bonds, which link the molecules into zigzag chains running along the b-axis direction. |
format | Online Article Text |
id | pubmed-3998562 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-39985622014-05-13 12-{[4-(4-Bromophenyl)piperazin-1-yl]methyl}-9α-hydroxy-4,8-dimethyl-3,14-dioxatricyclo[9.3.0.0(2,4)]tetradec-7-en-13-one Loubidi, Mohamed Benharref, Ahmed El Ammari, Lahcen Saadi, Mohamed Berraho, Moha Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(25)H(33)BrN(2)O(4), was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylen-3,14-dioxa-tricyclo[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 molecule is built up from two fused five- and ten-membered rings with an additional epoxy ring system and a bromophenylpiperazine group as a substituent. The ten-membered ring adopts an approximate chair–chair–chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring shows an envelope conformation with the C atom closest to the hydroxy group forming the flap. An intramolecular O—H⋯N hydrogen bond stabilizes the molecular conformation. The crystal packing features C—H⋯O hydrogen bonds, which link the molecules into zigzag chains running along the b-axis direction. International Union of Crystallography 2014-03-29 /pmc/articles/PMC3998562/ /pubmed/24826186 http://dx.doi.org/10.1107/S1600536814006473 Text en © Loubidi et al. 2014 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 Loubidi, Mohamed Benharref, Ahmed El Ammari, Lahcen Saadi, Mohamed Berraho, Moha 12-{[4-(4-Bromophenyl)piperazin-1-yl]methyl}-9α-hydroxy-4,8-dimethyl-3,14-dioxatricyclo[9.3.0.0(2,4)]tetradec-7-en-13-one |
title | 12-{[4-(4-Bromophenyl)piperazin-1-yl]methyl}-9α-hydroxy-4,8-dimethyl-3,14-dioxatricyclo[9.3.0.0(2,4)]tetradec-7-en-13-one |
title_full | 12-{[4-(4-Bromophenyl)piperazin-1-yl]methyl}-9α-hydroxy-4,8-dimethyl-3,14-dioxatricyclo[9.3.0.0(2,4)]tetradec-7-en-13-one |
title_fullStr | 12-{[4-(4-Bromophenyl)piperazin-1-yl]methyl}-9α-hydroxy-4,8-dimethyl-3,14-dioxatricyclo[9.3.0.0(2,4)]tetradec-7-en-13-one |
title_full_unstemmed | 12-{[4-(4-Bromophenyl)piperazin-1-yl]methyl}-9α-hydroxy-4,8-dimethyl-3,14-dioxatricyclo[9.3.0.0(2,4)]tetradec-7-en-13-one |
title_short | 12-{[4-(4-Bromophenyl)piperazin-1-yl]methyl}-9α-hydroxy-4,8-dimethyl-3,14-dioxatricyclo[9.3.0.0(2,4)]tetradec-7-en-13-one |
title_sort | 12-{[4-(4-bromophenyl)piperazin-1-yl]methyl}-9α-hydroxy-4,8-dimethyl-3,14-dioxatricyclo[9.3.0.0(2,4)]tetradec-7-en-13-one |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998562/ https://www.ncbi.nlm.nih.gov/pubmed/24826186 http://dx.doi.org/10.1107/S1600536814006473 |
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