RESUMEN

Reported is the synthesis of azo mutual prodrugs of the nonsteroidal anti-inflammatory agents (NSAIDs) 4-aminophenylacetic acid (4-APAA) or 5-aminosalicylic acid (5-ASA) with peptides, including an antibiotic peptide temporin analogue modified at the amino terminal by an α-aminoisobutyric acid (Aib) residue. These prodrugs are designed for colonic delivery of two agents to treat infection and inflammation by the bacterial pathogen Clostridium difficile .

Asunto(s)

Ácidos Aminoisobutíricos/síntesis química , Antibacterianos/síntesis química , Antiinflamatorios no Esteroideos/síntesis química , Compuestos Azo/síntesis química , Péptidos/química , Profármacos/síntesis química , Ácidos Aminoisobutíricos/química , Ácidos Aminoisobutíricos/farmacología , Antibacterianos/química , Antibacterianos/farmacología , Antiinflamatorios no Esteroideos/química , Antiinflamatorios no Esteroideos/farmacología , Compuestos Azo/química , Compuestos Azo/farmacología , Clostridioides difficile/efectos de los fármacos , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Péptidos/farmacología , Profármacos/química , Profármacos/farmacología

RESUMEN

The title mol-ecule, C(21)H(18)O(8), crystallizes in two crystal polymorphs, see also Nallasivam, Nethaji, Vembu & Jaswant [Acta Cryst. (2009), E65, o314-o315]. The mol-ecules of both polymorphs differ by the conformation of the oxomethyl-acetate groups. The title mol-ecules are rather planar compared to the mol-ecules of the other polymorph. In the title mol-ecule, one of the oxomethyl-acetate groups is disordered (occupancies of 0.6058/0.3942). The structures of both polymorphs are stabilized by C-H⋯O and C-H⋯π inter-actions. Due to the planarity of the title mol-ecules and similar inter-molecular inter-actions, the title mol-ecules are more densely packed than those of the other polymorph.

RESUMEN

The title mol-ecule, C(21)H(18)O(8), crystallizes in two crystal polymorphs, see also Nallasivam, Nethaji, Vembu & Jaswant [Acta Cryst. (2009), E65, o312-o313]. The main difference between the two polymorphs is in the conformation of the oxomethyl-acetate groups with regard to the almost planar [total puckering amplitude 0.047 (2) Å] chromene ring. In the title compound, the best planes of the oxomethyl-acetate groups through the non-H atoms are almost perpendicular to the chromene ring [making dihedral angles of 89.61 (6) and 80.59 (5)°], while in the second polymorph the mol-ecules are close to planar. Both crystal structures are stabilized by C-H⋯O.

RESUMEN

The asymmetric unit of the title compound, C(17)H(14)O(4), contains two independent mol-ecules which differ in the relative orientations of the phenyl rings with repect to the essentially planar [maximum deviations of 0.029 (2) and 0.050 (2) Šin the two mol-ecules] chromene fused-ring system, forming dihedral angles of 10.3 (5) and 30.86 (5)° in the two mol-ecules. The crystal structure is stabilized by weak C-H⋯O and C--H⋯π inter-actions, and π-π stacking inter-actions.

RESUMEN

In the title compound, C(17)H(10)Br(2)O(5), the chromene ring is almost planar with minimal puckering [total puckering amplitude = 0.067 (4) Å]. The dihedral angle between chromeme ring system and phenyl ring is 3.7 (2)°. The crystal structure is stabilized by intermolecular C-H⋯O inter-actions and an intramolecular O-H⋯O hydrogen bond also occurs.

RESUMEN

In the title compound, C(14)H(17)N(3)O(2)·0.5H(2)O, the asymmetric unit consists of an N,N'-(phenyl-imino-dimethyl-ene)diprop-2-enamide mol-ecule and one half-mol-ecule of water, with the O atom of the latter having 2 site symmetry. The supra-molecular architecture is framed by the inter-play of two-dimensional networks of both O-H⋯O and N-H⋯O inter-actions supported by C-H⋯O and edge-to-face C-H⋯π inter-actions.

RESUMEN

In the title mol-ecule, C(12)H(8)BrNO(5)S, the dihedral angle between the two benzene rings is 30.02 (7)°. The crystal structure is stabilized by weak C-H⋯O inter-actions.

RESUMEN

In the title mol-ecule, C(12)H(7)BrCl(2)O(3)S, the dihedral angle between the two benzene rings is 55.18 (5)°. The notable inter-molecular contacts include C-H⋯O and π-π inter-actions [centroid-centroid distances = 4.037 (1) and 3.349 (1) Å].

RESUMEN

The 1,3-benzodioxole ring systems in the title compound, C(22)H(22)O(8), are almost planar. The perhydro-furofuranyl system linking them adopts a distorted double-envelope conformation. Supra-molecular aggregation is effected by C-H⋯O, C-H⋯π and π-π [centroid-centroid distance of 3.755 Å, inter-planar distance of 3.633 Šand dihedral angle of 14.6°] inter-actions.

RESUMEN

In the title compound, C(29)H(22)O(4), the chromene ring is almost planar with a small puckering [0.143 (2) Å]. The crystal structure is stabilized by C-H⋯O and C-H⋯π inter-actions. Edge-to-face (centroid-centroid distances of 3.894 and 3.673 Å) and face-to-face (centroid-centroid distance of 3.460 Å) π-π-ring electron inter-actions are also observed.

RESUMEN

In the title compound, C(21)H(18)O(4), tthe dihedral angle between the chromene ring system and the pendant phenyl ring is 6.1 (1)°. The crystal structure is stabilized by an intermolecular C-H⋯O and C-H⋯π inter-actions.

RESUMEN

In the title compound, C(8)H(12)N(+)·C(6)H(2)N(3)O(7) (-), there are N-H⋯O and C-H⋯O inter-actions which generate R(2) (1)(5), R(2) (1)(6) and R(1) (2)(6) ring motifs. The supra-molecular aggregation is completed by the presence of edge-to-face and offset face-to-face π-π inter-actions with centroid-centroid distances of 3.673 and 3.697 Å, respectively.

RESUMEN

There are two independent formula units in the asymmetric unit of the title compound, C(4)H(10)NO(+)·C(6)H(2)N(3)O(7) (-). The morpholinium cations in both mol-ecules are puckered and adopt a chair conformation. Intermolecular N-H⋯O and C-H⋯O inter-actions generate rings of motifs R(2) (1)(5) and R(1) (2)(6). The supra-molecular aggregation is completed by the presence of two co-operative hydrogen-bonded networks of further N-H⋯O inter-actions, which generate an infinite one-dimensional chain along the base vector [100]. Two C-H⋯π interactions are also seen.

RESUMEN

The indole and phenyl ring systems in the title compound, C(18)H(18)N(2)S(2), are nearly coplanar, the indole and phenyl planes forming a dihedral angle of 6.5 (1)°. Supra-molecular aggregation is effected by N-H⋯S, C-H⋯S, N-H⋯π and C-H⋯π inter-actions. The crystal studied exhibited inversion twinning.

RESUMEN

The structures of the title compounds, C(12)H(8)N(2)O(7)S and C(12)H(8)ClNO(5)S, contain weak C-H.O interactions creating layers of molecules which, taking the conformation of the molecules into account, are arranged in an ABAB sequence. Both structures can be designated, therefore, as ordered racemates of rotameric species.

RESUMEN

In 2-chlorophenyl 3-nitrobenzenesulfonate, C(12)H(8)ClNO(5)S, and 2,4-dichlorophenyl 3-nitrobenzenesulfonate, C(12)H(7)Cl(2)NO(5)S, weak C-H...O interactions generate S(5), S(6) and R(2)(2)(7) rings. The supramolecular aggregation is completed by the presence of pi-pi interactions and intermolecular van der Waals short contacts.