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A comparison of the structures of some 2- and 3-substituted chromone derivatives: a structural study on the importance of the secondary carboxamide backbone for the inhibitory activity of MAO-B.

Gomes LR, Low JN, Cagide F, Gaspar A, Borges F - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: Their structural features are discussed and compared with similar compounds namely with respect to their MAO-B inhibitory activities.The pyrrolidine derivatives also display a significant twist: the dihedral angles between the chromone system and the best plane formed by the pyrrolidine atoms are 48.9 (2) and 23.97 (12)° in (3) and (4), respectively.A simple statistical analysis of their geometric parameters is made in order to compare them with those of the mol-ecules determined in the present work.

View Article: PubMed Central - HTML - PubMed

Affiliation: FP-ENAS-Faculdade de Ciências de Saúde, Escola Superior de Saúde da UFP, Universidade Fernando Pessoa, Rua Carlos da Maia, 296, P-4200-150 Porto, Portugal ; REQUIMTE/Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, 4169-007 Porto, Portugal.

ABSTRACT
The crystal structures of the 3-substituted tertiary chromone carboxamide derivative, C17H13NO3, N-methyl-4-oxo-N-phenyl-4H-chromene-3-carboxamide (1), and the chromone carbonyl pyrrolidine derivatives, C14H13NO3, 3-(pyrrolidine-1-carbon-yl)-4H-chromen-4-one (3) and 2-(pyrrolidine-1-carbon-yl)-4H-chromen-4-one (4) have been determined. Their structural features are discussed and compared with similar compounds namely with respect to their MAO-B inhibitory activities. The chromone carboxamide presents a -syn conformation with the aromatic rings twisted with respect to each other [the dihedral angle between the mean planes of the chromone system and the exocyclic phenyl ring is 58.48 (8)°]. The pyrrolidine derivatives also display a significant twist: the dihedral angles between the chromone system and the best plane formed by the pyrrolidine atoms are 48.9 (2) and 23.97 (12)° in (3) and (4), respectively. Compound (3) shows a short C-H⋯O intra-molecular contact forming an S(7) ring. The supra-molecular structures for each compound are defined by weak C-H⋯O hydrogen bonds, which link the mol-ecules into chains and sheets. The Cambridge Structural Database gave 45 hits for compounds with a pyrrolidinecarbonyl group. A simple statistical analysis of their geometric parameters is made in order to compare them with those of the mol-ecules determined in the present work.

No MeSH data available.


Related in: MedlinePlus

A view of the asymmetric unit of (4) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 70% probability level.
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fig3: A view of the asymmetric unit of (4) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 70% probability level.

Mentions: As mentioned above, the compounds discussed in this work are presented in the Scheme. Compounds (2), (5) and (6) have previously been characterized. The ellipsoid plots for the remaining structures, e.g. for (1), (3) and (4), are given in Figs. 1 ▸–3 ▸ ▸. The results of the biological tests show that only (5) exhibits significant IMAO-B activity. Its isomer (6) is much less active while the remaining ones are inactive towards MAO-B, suggesting that substitution on position number 3 of the chromone is required and it must be a secondary carboxamide. As will be discussed, the presence of a tertiary amide induces significant conformational changes to the compounds that can explain the lack of activity for those compounds.


A comparison of the structures of some 2- and 3-substituted chromone derivatives: a structural study on the importance of the secondary carboxamide backbone for the inhibitory activity of MAO-B.

Gomes LR, Low JN, Cagide F, Gaspar A, Borges F - Acta Crystallogr E Crystallogr Commun (2015)

A view of the asymmetric unit of (4) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 70% probability level.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4645046&req=5

fig3: A view of the asymmetric unit of (4) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 70% probability level.
Mentions: As mentioned above, the compounds discussed in this work are presented in the Scheme. Compounds (2), (5) and (6) have previously been characterized. The ellipsoid plots for the remaining structures, e.g. for (1), (3) and (4), are given in Figs. 1 ▸–3 ▸ ▸. The results of the biological tests show that only (5) exhibits significant IMAO-B activity. Its isomer (6) is much less active while the remaining ones are inactive towards MAO-B, suggesting that substitution on position number 3 of the chromone is required and it must be a secondary carboxamide. As will be discussed, the presence of a tertiary amide induces significant conformational changes to the compounds that can explain the lack of activity for those compounds.

Bottom Line: Their structural features are discussed and compared with similar compounds namely with respect to their MAO-B inhibitory activities.The pyrrolidine derivatives also display a significant twist: the dihedral angles between the chromone system and the best plane formed by the pyrrolidine atoms are 48.9 (2) and 23.97 (12)° in (3) and (4), respectively.A simple statistical analysis of their geometric parameters is made in order to compare them with those of the mol-ecules determined in the present work.

View Article: PubMed Central - HTML - PubMed

Affiliation: FP-ENAS-Faculdade de Ciências de Saúde, Escola Superior de Saúde da UFP, Universidade Fernando Pessoa, Rua Carlos da Maia, 296, P-4200-150 Porto, Portugal ; REQUIMTE/Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, 4169-007 Porto, Portugal.

ABSTRACT
The crystal structures of the 3-substituted tertiary chromone carboxamide derivative, C17H13NO3, N-methyl-4-oxo-N-phenyl-4H-chromene-3-carboxamide (1), and the chromone carbonyl pyrrolidine derivatives, C14H13NO3, 3-(pyrrolidine-1-carbon-yl)-4H-chromen-4-one (3) and 2-(pyrrolidine-1-carbon-yl)-4H-chromen-4-one (4) have been determined. Their structural features are discussed and compared with similar compounds namely with respect to their MAO-B inhibitory activities. The chromone carboxamide presents a -syn conformation with the aromatic rings twisted with respect to each other [the dihedral angle between the mean planes of the chromone system and the exocyclic phenyl ring is 58.48 (8)°]. The pyrrolidine derivatives also display a significant twist: the dihedral angles between the chromone system and the best plane formed by the pyrrolidine atoms are 48.9 (2) and 23.97 (12)° in (3) and (4), respectively. Compound (3) shows a short C-H⋯O intra-molecular contact forming an S(7) ring. The supra-molecular structures for each compound are defined by weak C-H⋯O hydrogen bonds, which link the mol-ecules into chains and sheets. The Cambridge Structural Database gave 45 hits for compounds with a pyrrolidinecarbonyl group. A simple statistical analysis of their geometric parameters is made in order to compare them with those of the mol-ecules determined in the present work.

No MeSH data available.


Related in: MedlinePlus