Cargando…
10α-Hydroxy-13-{[4-(4-methoxyphenyl)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(26)H(36)N(2)O(6), 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 fro...
Autores principales: | , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2012
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3295488/ https://www.ncbi.nlm.nih.gov/pubmed/22412599 http://dx.doi.org/10.1107/S1600536812005818 |
_version_ | 1782225589255536640 |
---|---|
author | Moumou, Mohamed Benharref, Ahmed Daran, Jean Claude Outouch, Rachid Berraho, Moha |
author_facet | Moumou, Mohamed Benharref, Ahmed Daran, Jean Claude Outouch, Rachid Berraho, Moha |
author_sort | Moumou, Mohamed |
collection | PubMed |
description | The title compound, C(26)H(36)N(2)O(6), 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 fused five- and ten-membered rings with two additional epoxy ring systems and a methoxyphenylpiperazine 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 determined by an O—H⋯N hydrogen bond between the hydroxy group and a piperazine N atom. The crystal structure is built up by weak C—H⋯O interactions. |
format | Online Article Text |
id | pubmed-3295488 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-32954882012-03-12 10α-Hydroxy-13-{[4-(4-methoxyphenyl)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 Daran, Jean Claude Outouch, Rachid Berraho, Moha Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(26)H(36)N(2)O(6), 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 fused five- and ten-membered rings with two additional epoxy ring systems and a methoxyphenylpiperazine 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 determined by an O—H⋯N hydrogen bond between the hydroxy group and a piperazine N atom. The crystal structure is built up by weak C—H⋯O interactions. International Union of Crystallography 2012-02-17 /pmc/articles/PMC3295488/ /pubmed/22412599 http://dx.doi.org/10.1107/S1600536812005818 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 Daran, Jean Claude Outouch, Rachid Berraho, Moha 10α-Hydroxy-13-{[4-(4-methoxyphenyl)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-(4-methoxyphenyl)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-(4-methoxyphenyl)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-(4-methoxyphenyl)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-(4-methoxyphenyl)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-(4-methoxyphenyl)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-(4-methoxyphenyl)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/PMC3295488/ https://www.ncbi.nlm.nih.gov/pubmed/22412599 http://dx.doi.org/10.1107/S1600536812005818 |
work_keys_str_mv | AT moumoumohamed 10ahydroxy1344methoxyphenylpiperazin1ylmethyl49dimethyl3815trioxatetracyclo1030024079pentadecan14one AT benharrefahmed 10ahydroxy1344methoxyphenylpiperazin1ylmethyl49dimethyl3815trioxatetracyclo1030024079pentadecan14one AT daranjeanclaude 10ahydroxy1344methoxyphenylpiperazin1ylmethyl49dimethyl3815trioxatetracyclo1030024079pentadecan14one AT outouchrachid 10ahydroxy1344methoxyphenylpiperazin1ylmethyl49dimethyl3815trioxatetracyclo1030024079pentadecan14one AT berrahomoha 10ahydroxy1344methoxyphenylpiperazin1ylmethyl49dimethyl3815trioxatetracyclo1030024079pentadecan14one |