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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.

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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.


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Compound (1): view of the sheets which lie parallel to [001] formed by the combination of the chains shown in Figs. 4 ▸ and 5 ▸. Hydrogen atoms not involved in the hydrogen bonding are omitted.
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fig6: Compound (1): view of the sheets which lie parallel to [001] formed by the combination of the chains shown in Figs. 4 ▸ and 5 ▸. Hydrogen atoms not involved in the hydrogen bonding are omitted.

Mentions: In compound (1) the C2—H2⋯O4(x + 1, y, z) and C5—H5⋯O1(x + 1, y, z) hydrogen bonds link the mol­ecules into (8) rings which link the, mol­ecules into chains running parallel to the a axis, Fig. 4 ▸. These chains are then linked by the C314—314⋯O3(x − 1, y + 1, z) hydrogen bond, Fig. 5 ▸, to form sheets lying parallel to [001], Fig. 6 ▸. A centrosymmetric sheet inter­penetrates the first sheet, and these two sheets are linked by π–π stacking between the chromone rings [centroid–centroid distance = 3.557 (2) Å].


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)

Compound (1): view of the sheets which lie parallel to [001] formed by the combination of the chains shown in Figs. 4 ▸ and 5 ▸. Hydrogen atoms not involved in the hydrogen bonding are omitted.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig6: Compound (1): view of the sheets which lie parallel to [001] formed by the combination of the chains shown in Figs. 4 ▸ and 5 ▸. Hydrogen atoms not involved in the hydrogen bonding are omitted.
Mentions: In compound (1) the C2—H2⋯O4(x + 1, y, z) and C5—H5⋯O1(x + 1, y, z) hydrogen bonds link the mol­ecules into (8) rings which link the, mol­ecules into chains running parallel to the a axis, Fig. 4 ▸. These chains are then linked by the C314—314⋯O3(x − 1, y + 1, z) hydrogen bond, Fig. 5 ▸, to form sheets lying parallel to [001], Fig. 6 ▸. A centrosymmetric sheet inter­penetrates the first sheet, and these two sheets are linked by π–π stacking between the chromone rings [centroid–centroid distance = 3.557 (2) Å].

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