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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.


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View of compounds in the CSD with C—H⋯O short intra­molecular contacts involving an o-pyrolidine hydrogen atom.
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fig14: View of compounds in the CSD with C—H⋯O short intra­molecular contacts involving an o-pyrolidine hydrogen atom.

Mentions: Intra­molecular C—H⋯O short contacts similar to that in (3) are found in five compounds in the CSD: LISLAB, 1-(1-pyrrolidinylcarbon­yl)cyclo­propyl sulfamate (Morin et al., 2007 ▸), PEQHAU, 2-[3′-(4′′-chloro­phen­yl)-4′,6′-di­meth­oxy­indol-7′-yl]glyoxyl-1-pyrrolidine (Black et al., 1997 ▸), QIBBEJ, [2-hy­droxy-5-(2-hy­droxy­benzo­yl)phen­yl](pyrrolidin-1-yl)methanone (Holtz et al., 2007 ▸), SINHAZ, 2-meth­oxy-1-(1-pyrrolidinylcarbon­yl)naphthalene (Sakamoto et al., 2007 ▸) and TAJDIR, (4S,5S)-4,5-bis­(pyrrolidinylcarbon­yl)-2,2-dimethyl-1,3-dioxolane (Garcia et al., 1991 ▸), Fig. 10 ▸. In LISLAB and TAJDIR, S(6) rings are formed. In QIBBEJ and SINHAZ, an S(7) ring similar to that in (2) is formed. In PEQHAU, an S(8) ring is formed, Fig. 14 ▸.


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)

View of compounds in the CSD with C—H⋯O short intra­molecular contacts involving an o-pyrolidine hydrogen atom.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig14: View of compounds in the CSD with C—H⋯O short intra­molecular contacts involving an o-pyrolidine hydrogen atom.
Mentions: Intra­molecular C—H⋯O short contacts similar to that in (3) are found in five compounds in the CSD: LISLAB, 1-(1-pyrrolidinylcarbon­yl)cyclo­propyl sulfamate (Morin et al., 2007 ▸), PEQHAU, 2-[3′-(4′′-chloro­phen­yl)-4′,6′-di­meth­oxy­indol-7′-yl]glyoxyl-1-pyrrolidine (Black et al., 1997 ▸), QIBBEJ, [2-hy­droxy-5-(2-hy­droxy­benzo­yl)phen­yl](pyrrolidin-1-yl)methanone (Holtz et al., 2007 ▸), SINHAZ, 2-meth­oxy-1-(1-pyrrolidinylcarbon­yl)naphthalene (Sakamoto et al., 2007 ▸) and TAJDIR, (4S,5S)-4,5-bis­(pyrrolidinylcarbon­yl)-2,2-dimethyl-1,3-dioxolane (Garcia et al., 1991 ▸), Fig. 10 ▸. In LISLAB and TAJDIR, S(6) rings are formed. In QIBBEJ and SINHAZ, an S(7) ring similar to that in (2) is formed. In PEQHAU, an S(8) ring is formed, Fig. 14 ▸.

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