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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

Compound (3): mol­ecular C(6) chain running parallel to the c axis. Mol­ecules i and ii are at (−x + , −y + 1, z + ) and (−x + , −y + 1, z − ), respectively. Hydrogen atoms not involved in the hydrogen bonding are omitted.
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fig7: Compound (3): mol­ecular C(6) chain running parallel to the c axis. Mol­ecules i and ii are at (−x + , −y + 1, z + ) and (−x + , −y + 1, z − ), respectively. Hydrogen atoms not involved in the hydrogen bonding are omitted.

Mentions: In compound (3) the mol­ecules are linked by C—H⋯O inter­actions and by C—H⋯π inter­actions. The C8—H8⋯O4(−x + , −y + 1, z + ) and C314—H31E⋯O3(−x + , −y + 2, z − ) contacts both form C(6) chains running parallel to the c axis which are propagated by the twofold screw axes at (, , z) and (, 1, z), respectively, Figs. 7 ▸ and 8 ▸. These combine to form a corrugated sheet in the bc plane, Fig. 9 ▸. The C2—H2⋯O4(x + , −y + , −z + 1) inter­action links the mol­ecules into C(5) chains running along the a axis propagated by the twofold screw axis at (x, , ), Fig. 10 ▸. The C6—H6⋯O4(−x + 1, y − , −z + ) inter­action links the mol­ecules into C(6) chains running along the b axis which are propagated by the twofold screw axis at (, y, ), Fig. 11 ▸. There is also a C—H⋯π inter­action C313—H31D⋯Cg(x − 2, y + , −z + ). These inter­actions combine to form a complex three-dimensional network.


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 (3): mol­ecular C(6) chain running parallel to the c axis. Mol­ecules i and ii are at (−x + , −y + 1, z + ) and (−x + , −y + 1, z − ), respectively. 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

fig7: Compound (3): mol­ecular C(6) chain running parallel to the c axis. Mol­ecules i and ii are at (−x + , −y + 1, z + ) and (−x + , −y + 1, z − ), respectively. Hydrogen atoms not involved in the hydrogen bonding are omitted.
Mentions: In compound (3) the mol­ecules are linked by C—H⋯O inter­actions and by C—H⋯π inter­actions. The C8—H8⋯O4(−x + , −y + 1, z + ) and C314—H31E⋯O3(−x + , −y + 2, z − ) contacts both form C(6) chains running parallel to the c axis which are propagated by the twofold screw axes at (, , z) and (, 1, z), respectively, Figs. 7 ▸ and 8 ▸. These combine to form a corrugated sheet in the bc plane, Fig. 9 ▸. The C2—H2⋯O4(x + , −y + , −z + 1) inter­action links the mol­ecules into C(5) chains running along the a axis propagated by the twofold screw axis at (x, , ), Fig. 10 ▸. The C6—H6⋯O4(−x + 1, y − , −z + ) inter­action links the mol­ecules into C(6) chains running along the b axis which are propagated by the twofold screw axis at (, y, ), Fig. 11 ▸. There is also a C—H⋯π inter­action C313—H31D⋯Cg(x − 2, y + , −z + ). These inter­actions combine to form a complex three-dimensional network.

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