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(1S,2R,3R,6R,7S,8R,10S,11S)-13-{[4-(4-Chlorophenyl)piperazin-1-yl]methyl}-10-hydroxy-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(33)ClN(2)O(5), 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 molecule is built up...
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/PMC3344091/ https://www.ncbi.nlm.nih.gov/pubmed/22606094 http://dx.doi.org/10.1107/S1600536812011816 |
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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(33)ClN(2)O(5), 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 molecule is built up from fused five- and ten-membered rings with two additional epoxy ring systems and a chlorophenylpiperazine group as a substituent. The ten-membered ring adopts an approximate 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. The molecular conformation is stabilized by an intramolecular O—H⋯N hydrogen bond between the hydroxy group and a piperazine N atom. The crystal structure is stabilized by weak C—H⋯O interactions. |
format | Online Article Text |
id | pubmed-3344091 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-33440912012-05-17 (1S,2R,3R,6R,7S,8R,10S,11S)-13-{[4-(4-Chlorophenyl)piperazin-1-yl]methyl}-10-hydroxy-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(33)ClN(2)O(5), 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 molecule is built up from fused five- and ten-membered rings with two additional epoxy ring systems and a chlorophenylpiperazine group as a substituent. The ten-membered ring adopts an approximate 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. The molecular conformation is stabilized by an intramolecular O—H⋯N hydrogen bond between the hydroxy group and a piperazine N atom. The crystal structure is stabilized by weak C—H⋯O interactions. International Union of Crystallography 2012-03-24 /pmc/articles/PMC3344091/ /pubmed/22606094 http://dx.doi.org/10.1107/S1600536812011816 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 (1S,2R,3R,6R,7S,8R,10S,11S)-13-{[4-(4-Chlorophenyl)piperazin-1-yl]methyl}-10-hydroxy-4,9-dimethyl-3,8,15-trioxatetracyclo[10.3.0.0(2,4).0(7,9)]pentadecan-14-one |
title | (1S,2R,3R,6R,7S,8R,10S,11S)-13-{[4-(4-Chlorophenyl)piperazin-1-yl]methyl}-10-hydroxy-4,9-dimethyl-3,8,15-trioxatetracyclo[10.3.0.0(2,4).0(7,9)]pentadecan-14-one |
title_full | (1S,2R,3R,6R,7S,8R,10S,11S)-13-{[4-(4-Chlorophenyl)piperazin-1-yl]methyl}-10-hydroxy-4,9-dimethyl-3,8,15-trioxatetracyclo[10.3.0.0(2,4).0(7,9)]pentadecan-14-one |
title_fullStr | (1S,2R,3R,6R,7S,8R,10S,11S)-13-{[4-(4-Chlorophenyl)piperazin-1-yl]methyl}-10-hydroxy-4,9-dimethyl-3,8,15-trioxatetracyclo[10.3.0.0(2,4).0(7,9)]pentadecan-14-one |
title_full_unstemmed | (1S,2R,3R,6R,7S,8R,10S,11S)-13-{[4-(4-Chlorophenyl)piperazin-1-yl]methyl}-10-hydroxy-4,9-dimethyl-3,8,15-trioxatetracyclo[10.3.0.0(2,4).0(7,9)]pentadecan-14-one |
title_short | (1S,2R,3R,6R,7S,8R,10S,11S)-13-{[4-(4-Chlorophenyl)piperazin-1-yl]methyl}-10-hydroxy-4,9-dimethyl-3,8,15-trioxatetracyclo[10.3.0.0(2,4).0(7,9)]pentadecan-14-one |
title_sort | (1s,2r,3r,6r,7s,8r,10s,11s)-13-{[4-(4-chlorophenyl)piperazin-1-yl]methyl}-10-hydroxy-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/PMC3344091/ https://www.ncbi.nlm.nih.gov/pubmed/22606094 http://dx.doi.org/10.1107/S1600536812011816 |
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