Cargando…
13-(Imidazol-1-yl)-11,13-dihydromelampomagnolide B monohydrate
The title compound, C(18)H(24)N(2)O(4)·H(2)O {systematic name: (1aR,7aS,8R,10aS,10bS,E)-5-hydroxymethyl-8-[(1H-imidazol-1-yl)methyl]-1a-methyl-2,3,6,7,7a,8,10a,10b-octahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-9(1aH)-one monohydrate}, an imidazole derivative of melampomagnolide B was synt...
Autores principales: | , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2013
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3885019/ https://www.ncbi.nlm.nih.gov/pubmed/24454194 http://dx.doi.org/10.1107/S1600536813029188 |
_version_ | 1782298692669145088 |
---|---|
author | Janganati, Venumadhav Penthala, Narsimha Reddy Parkin, Sean Crooks, Peter A. |
author_facet | Janganati, Venumadhav Penthala, Narsimha Reddy Parkin, Sean Crooks, Peter A. |
author_sort | Janganati, Venumadhav |
collection | PubMed |
description | The title compound, C(18)H(24)N(2)O(4)·H(2)O {systematic name: (1aR,7aS,8R,10aS,10bS,E)-5-hydroxymethyl-8-[(1H-imidazol-1-yl)methyl]-1a-methyl-2,3,6,7,7a,8,10a,10b-octahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-9(1aH)-one monohydrate}, an imidazole derivative of melampomagnolide B was synthesized under Michael addition conditions. The molecule is built up from fused ten-, five- (lactone) and three-membered (epoxide) rings. The internal double bond of the ten-membered ring identifies it as the cis or E isomer. The lactone ring has an envelope-type conformation, with the (chiral) C atom opposite the lactone O atoms as the flap atom. In the crystal, O—H⋯O, O—H⋯N and weak C—H⋯O hydrogen bonds link the molecules (along with water) into sheets parallel to the bc plane. |
format | Online Article Text |
id | pubmed-3885019 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-38850192014-01-17 13-(Imidazol-1-yl)-11,13-dihydromelampomagnolide B monohydrate Janganati, Venumadhav Penthala, Narsimha Reddy Parkin, Sean Crooks, Peter A. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(18)H(24)N(2)O(4)·H(2)O {systematic name: (1aR,7aS,8R,10aS,10bS,E)-5-hydroxymethyl-8-[(1H-imidazol-1-yl)methyl]-1a-methyl-2,3,6,7,7a,8,10a,10b-octahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-9(1aH)-one monohydrate}, an imidazole derivative of melampomagnolide B was synthesized under Michael addition conditions. The molecule is built up from fused ten-, five- (lactone) and three-membered (epoxide) rings. The internal double bond of the ten-membered ring identifies it as the cis or E isomer. The lactone ring has an envelope-type conformation, with the (chiral) C atom opposite the lactone O atoms as the flap atom. In the crystal, O—H⋯O, O—H⋯N and weak C—H⋯O hydrogen bonds link the molecules (along with water) into sheets parallel to the bc plane. International Union of Crystallography 2013-11-06 /pmc/articles/PMC3885019/ /pubmed/24454194 http://dx.doi.org/10.1107/S1600536813029188 Text en © Janganati et al. 2013 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 Janganati, Venumadhav Penthala, Narsimha Reddy Parkin, Sean Crooks, Peter A. 13-(Imidazol-1-yl)-11,13-dihydromelampomagnolide B monohydrate |
title | 13-(Imidazol-1-yl)-11,13-dihydromelampomagnolide B monohydrate |
title_full | 13-(Imidazol-1-yl)-11,13-dihydromelampomagnolide B monohydrate |
title_fullStr | 13-(Imidazol-1-yl)-11,13-dihydromelampomagnolide B monohydrate |
title_full_unstemmed | 13-(Imidazol-1-yl)-11,13-dihydromelampomagnolide B monohydrate |
title_short | 13-(Imidazol-1-yl)-11,13-dihydromelampomagnolide B monohydrate |
title_sort | 13-(imidazol-1-yl)-11,13-dihydromelampomagnolide b monohydrate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3885019/ https://www.ncbi.nlm.nih.gov/pubmed/24454194 http://dx.doi.org/10.1107/S1600536813029188 |
work_keys_str_mv | AT janganativenumadhav 13imidazol1yl1113dihydromelampomagnolidebmonohydrate AT penthalanarsimhareddy 13imidazol1yl1113dihydromelampomagnolidebmonohydrate AT parkinsean 13imidazol1yl1113dihydromelampomagnolidebmonohydrate AT crookspetera 13imidazol1yl1113dihydromelampomagnolidebmonohydrate |