Publication
New insights in the discovery of novelh-MAO-B inhibitors: structural characterization of a series ofN-phenyl-4-oxo-4H-chromene-3-carboxamide derivatives
| dc.contributor.author | Gomes, Ligia R. | |
| dc.contributor.author | Low, John Nicolson | |
| dc.contributor.author | Cagide, Fernando | |
| dc.contributor.author | Chavarria, Daniel | |
| dc.contributor.author | Borges, Fernanda | |
| dc.date.accessioned | 2019-10-24T17:37:17Z | |
| dc.date.available | 2019-10-24T17:37:17Z | |
| dc.date.issued | 2015 | |
| dc.description.abstract | Six N-substituted-phenyl 4-oxo-4H-chromene-3-carboxamides, namely N-(2-nitrophenyl)-4-oxo-4H-chromene-3-carboxamide, C16H10N2O5 (2b), N-(3-methoxyphenyl)-4-oxo-4H-chromene-3-carboxamide, C17H13NO4, (3a), N-(3-bromophenyl)-4-oxo-4H-chromene-3-carboxamide, C16H10BrNO3, (3b), N-(4-methoxyphenyl)-4-oxo-4H-chromene-3-carboxamide, C17H13NO4, (4a), N-(4-methylphenyl)-4-oxo-4H-chromene-3-carboxamide, C17H13NO3, (4d), and N-(4-hydroxyphenyl)-4-oxo-4H-chromene-3-carboxamide, C16H11NO4, (4e), have been structurally characterized. All compounds exhibit an anti conformation with respect to the C—N rotamer of the amide and a trans-related conformation with the carbonyl groups of the chromone ring of the amide. These structures present an intramolecular hydrogen-bonded network comprising an N—H⋯O hydrogen bond between the amide N atom and the O atom of the carbonyl group of the pyrone ring, forming an S(6) ring, and a weak Car—H⋯O hydrogen bond in which the carbonyl group of the amide acts as acceptor for the H atom of an ortho-C atom of the exocyclic phenyl ring, which results in another S(6) ring. The N—H⋯O intramolecular hydrogen bond constrains the carboxamide moiety such that it is virtually coplanar with the chromone ring. | pt_PT |
| dc.description.version | info:eu-repo/semantics/publishedVersion | pt_PT |
| dc.identifier.citation | Gomes, L. R., Low, J. N., Cagide, F., Chavarria, D., & Borges, F. (2015). New insights in the discovery of novel h-MAO-B inhibitors: structural characterization of a series of N-phenyl-4-oxo-4H-chromene-3-carboxamide derivatives. Acta crystallographica. Section E, Crystallographic communications, 71(Pt 5), 547–554. doi:10.1107/S2056989015007859 | pt_PT |
| dc.identifier.doi | 10.1107/S2056989015007859 | pt_PT |
| dc.identifier.issn | 2056-9890 | |
| dc.identifier.uri | http://hdl.handle.net/10284/8167 | |
| dc.language.iso | eng | pt_PT |
| dc.peerreviewed | yes | pt_PT |
| dc.publisher | International Union of Crystallography | pt_PT |
| dc.relation.publisherversion | http://scripts.iucr.org/cgi-bin/paper?lh5762 | pt_PT |
| dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | pt_PT |
| dc.subject | Crystal structure | pt_PT |
| dc.subject | Drug design | pt_PT |
| dc.subject | Chromones | pt_PT |
| dc.subject | Conformation | pt_PT |
| dc.subject | Supramolecular structure | pt_PT |
| dc.subject | Hydrogen bonding | pt_PT |
| dc.title | New insights in the discovery of novelh-MAO-B inhibitors: structural characterization of a series ofN-phenyl-4-oxo-4H-chromene-3-carboxamide derivatives | pt_PT |
| dc.type | journal article | |
| dspace.entity.type | Publication | |
| oaire.citation.endPage | 554 | pt_PT |
| oaire.citation.issue | 5 | pt_PT |
| oaire.citation.startPage | 547 | pt_PT |
| oaire.citation.title | Acta Crystallographica Section E: Crystallographic Communications | pt_PT |
| oaire.citation.volume | 71 | pt_PT |
| person.familyName | Maria da Silva Rebelo Gomes | |
| person.givenName | Lígia | |
| person.identifier.ciencia-id | A41A-22BE-18F0 | |
| person.identifier.orcid | 0000-0002-3496-6052 | |
| rcaap.rights | openAccess | pt_PT |
| rcaap.type | article | pt_PT |
| relation.isAuthorOfPublication | 66614656-b892-46ad-93f3-7586580fd733 | |
| relation.isAuthorOfPublication.latestForDiscovery | 66614656-b892-46ad-93f3-7586580fd733 |