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Crystal structures of butyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate and 2-methoxyethyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate
The title benzofuran derivatives 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate (BF1), C(19)H(18)N(2)O(6), and 2-methoxyethyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate (BF2), C(18)H(16)N(2)O(7), recently attracted attention because of their promising anti...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6658937/ https://www.ncbi.nlm.nih.gov/pubmed/31391987 http://dx.doi.org/10.1107/S205698901900728X |
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author | Diana, Rosita Tuzi, Angela Panunzi, Barbara Carella, Antonio Caruso, Ugo |
author_facet | Diana, Rosita Tuzi, Angela Panunzi, Barbara Carella, Antonio Caruso, Ugo |
author_sort | Diana, Rosita |
collection | PubMed |
description | The title benzofuran derivatives 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate (BF1), C(19)H(18)N(2)O(6), and 2-methoxyethyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate (BF2), C(18)H(16)N(2)O(7), recently attracted attention because of their promising antitumoral activity. BF1 crystallizes in the space group P [Image: see text]. BF2 in the space group P21/c. The nitrophenyl group is inclined to benzofuran moiety with a dihedral angle between their mean planes of 69.2 (2)° in BF1 and 60.20 (6)° in BF2. A common feature in the molecular structures of BF1 and BF2 is the intramolecular N—H⋯O(carbonyl) hydrogen bond. In the crystal of BF1, the molecules are linked head-to-tail into a one-dimensional hydrogen-bonding pattern along the a-axis direction. In BF2, pairs of head-to-tail hydrogen-bonded chains of molecules along the b-axis direction are linked by O—H⋯O(methoxy) hydrogen bonds. In BF1, the butyl group is disordered over two orientations with occupancies of 0.557 (13) and 0.443 (13). |
format | Online Article Text |
id | pubmed-6658937 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-66589372019-08-07 Crystal structures of butyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate and 2-methoxyethyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate Diana, Rosita Tuzi, Angela Panunzi, Barbara Carella, Antonio Caruso, Ugo Acta Crystallogr E Crystallogr Commun Research Communications The title benzofuran derivatives 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate (BF1), C(19)H(18)N(2)O(6), and 2-methoxyethyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate (BF2), C(18)H(16)N(2)O(7), recently attracted attention because of their promising antitumoral activity. BF1 crystallizes in the space group P [Image: see text]. BF2 in the space group P21/c. The nitrophenyl group is inclined to benzofuran moiety with a dihedral angle between their mean planes of 69.2 (2)° in BF1 and 60.20 (6)° in BF2. A common feature in the molecular structures of BF1 and BF2 is the intramolecular N—H⋯O(carbonyl) hydrogen bond. In the crystal of BF1, the molecules are linked head-to-tail into a one-dimensional hydrogen-bonding pattern along the a-axis direction. In BF2, pairs of head-to-tail hydrogen-bonded chains of molecules along the b-axis direction are linked by O—H⋯O(methoxy) hydrogen bonds. In BF1, the butyl group is disordered over two orientations with occupancies of 0.557 (13) and 0.443 (13). International Union of Crystallography 2019-05-24 /pmc/articles/PMC6658937/ /pubmed/31391987 http://dx.doi.org/10.1107/S205698901900728X Text en © Diana et al. 2019 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/ |
spellingShingle | Research Communications Diana, Rosita Tuzi, Angela Panunzi, Barbara Carella, Antonio Caruso, Ugo Crystal structures of butyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate and 2-methoxyethyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate |
title | Crystal structures of butyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate and 2-methoxyethyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate |
title_full | Crystal structures of butyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate and 2-methoxyethyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate |
title_fullStr | Crystal structures of butyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate and 2-methoxyethyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate |
title_full_unstemmed | Crystal structures of butyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate and 2-methoxyethyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate |
title_short | Crystal structures of butyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate and 2-methoxyethyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate |
title_sort | crystal structures of butyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate and 2-methoxyethyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6658937/ https://www.ncbi.nlm.nih.gov/pubmed/31391987 http://dx.doi.org/10.1107/S205698901900728X |
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