RESUMEN

A new series of N-[5-(4-(alkyl/aryl)-3-nitro-phenyl)-[1,3,4-thiadiazol-2-yl]-2,2-dimethyl-propionamide 4 (a-l) and 6-(4-Methoxy-phenyl)-2-(4-alkyl/aryl)-3-nitro-phenyl)-Imidazo [2,1-b] [1,3,4] thiadiazole 6 (a-l) were synthesized starting from 5-(4-Fluoro-3-nitro-phenyl)-[1,3,4] thiadiazole-2-ylamine. The synthesized compounds were characterized by IR, NMR, mass spectral and elemental analysis. All the compounds were tested for antibacterial and antifungal activities. The antimicrobial activities of the compounds were assessed by well plate method (zone of inhibition). Compounds 4a, 4c and 6e, 6g displayed appreciable activity at the concentration 0.5-1.0 mg/mL.

Asunto(s)

Antibacterianos/química , Antibacterianos/farmacología , Antifúngicos/química , Antifúngicos/farmacología , Tiadiazoles/química , Tiadiazoles/farmacología , Antibacterianos/síntesis química , Antifúngicos/síntesis química , Bacterias/efectos de los fármacos , Infecciones Bacterianas/tratamiento farmacológico , Hongos/efectos de los fármacos , Humanos , Pruebas de Sensibilidad Microbiana , Micosis/tratamiento farmacológico , Tiadiazoles/síntesis química

RESUMEN

In the title compound, C(24)H(20)BrF(2)N(3)O(3)S, the triazole ring (r.m.s. deviation = 0.0107 Å) makes dihedral angles of 28.18 (14), 63.76 (14) and 77.01 (18)°, respectively, with the trimeth-oxy-, bromo-, and difluoro-substituted benzene rings. The C atoms of the meta meth-oxy groups are roughly coplanar with their ring [displacements = -0.289 (4) and 0.083 (7) Å], whereas the C atom of the para group is displaced [1.117 (3) Å]. In the crystal, inversion dimers linked by two pairs of C-H⋯O hydrogen bonds occur. The ring motif of the two hydrogen bonds to their symmetry-generated O-atom acceptors is R(2) (2)(8).

RESUMEN

In the crystal structur of the achiral title compound, C(9)H(8)N(2), N-H⋯N hydrogen bonds connect the mol-ecules into zigzag chains in [100]. Weak inter-molecular N-H⋯π inter-actions further consolidate the crystal packing.

RESUMEN

In the title compound, C(24)H(20)ClF(2)N(3)O(3)S, the essentially planar triazole ring (r.m.s. deviation = 0.001 Å) forms dihedral angles of 22.35 (10), 68.17 (10) and 42.01 (10)° with the mean planes of the trimeth-oxy-phenyl, chloro-phenyl and difluoro-phenyl rings, respectively. A weak intra-molecular C-H⋯π inter-action occurs. In the crystal, mol-ecules are linked into sheets lying parallel to the bc plane by C-H⋯O and C-H⋯N hydrogen bonds. The crystal packing also features weak C-H⋯π inter-actions.

RESUMEN

In the title compound, C(19)H(24)N(2)O(3), the benzene ring forms a dihedral angle of 65.34 (7)° with the pyrazole ring. The cyclo-hexane ring adopts a chair conformation. In the crystal, mol-ecules are linked into a inversion dimers by pairs of C-H⋯O hydrogen bonds, generating R(2) (2)(22) ring motifs.

RESUMEN

In the title compound, C(17)H(20)N(2)O(3), the meth-oxy-phenyl unit is disordered over two sets of sites in a 0.715 (4):0.285 (4) ratio. The pyrazole ring forms dihedral angles of 55.88 (16) and 72.6 (4)° with the benzene rings of its major and minor components, respectively. The cyclo-hexane ring adopts a chair conformation and its C-N bond is in an equatorial orientation. In the crystal, mol-ecules are linked into inversion dimers by pairs of O-H⋯O hydrogen bonds, generating R(2) (2)(8) loops.

RESUMEN

The asymmetric unit of the title compound, C(5)H(2)Cl(2)N(2)O(2), consists of two crystallographically independent mol-ecules. The pyridine ring in each mol-ecule is essentially planar, with maximum deviations of 0.004 (4) and 0.007 (4) Å. Short Cl⋯O [3.09 (3) and 3.13 (4) Å] and Cl⋯Cl [3.38 (12) Å] contacts were observed. No significant inter-molecular inter-actions were observed in the crystal packing.

RESUMEN

In the title mol-ecular salt, C(11)H(17)N(2) (+)·Cl(-), the piperazin-1-ium ring adopts a chair conformation with the aromatic ring in a pseudo-equatorial orientation. The dihedral angle between the benzene ring and the mean plane of the piperazin-1-ium ring is 51.22 (6)°. In the crystal, N-H⋯Cl hydrogen bonds link the mol-ecules into chains propagating in [100]. Weak C-H⋯π inter-actions also ocur.

RESUMEN

In the present study a series of new 1,3,4-oxadiazole derivatives containing 2-fluoro-4-methoxy moiety were synthesized. These newly synthesized compounds were characterized by NMR, mass spectral, IR spectral study and also by C, H, N analyses. All the newly synthesized compounds were screened for their antibacterial and antifungal studies. Antimicrobial studies revealed that compounds 4a and 4b showed significant antibacterial activity against Escherichia coli and Pseudomonas aeruginosa Compound 4i showed significant antifungal activity against C. albicans.

Asunto(s)

Antibacterianos , Antiinfecciosos , Bacterias/efectos de los fármacos , Hongos/efectos de los fármacos , Oxadiazoles , Antibacterianos/síntesis química , Antibacterianos/química , Antibacterianos/farmacología , Antiinfecciosos/síntesis química , Antiinfecciosos/química , Antiinfecciosos/farmacología , Flúor/química , Espectroscopía de Resonancia Magnética , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Oxadiazoles/síntesis química , Oxadiazoles/química , Oxadiazoles/farmacología , Espectrofotometría Infrarroja

RESUMEN

The mol-ecule of the title compound, C(3)H(2)ClN(3)O(2), is almost planar; the dihedral angle between the imidazole ring and the nitro group is 1.7 (2)°. In the crystal structure, pairs of inter-molecular C-H⋯O hydrogen bonds link inversion-related mol-ecules into dimers, generating R(2) (2)(10) ring motifs. The dimers are inter-connected into two-dimensional networks parallel to (102) via inter-molecular N-H⋯N hydrogen bonds. Further stabilization is provided by short inter-molecular Cl⋯O inter-actions [3.142 (2) and 3.1475 (19) Å].

RESUMEN

In the title compound, C(16)H(20)N(2)O(2), the pyrazole ring is essentially planar [maximum deviation = 0.008 (2) Å] and is inclined at an angle of 82.82 (10)° with respect to the phenyl ring. The crystal packing is consolidated by pairs of inter-molecular C-H⋯O hydrogen bonds, which link the mol-ecules into centrosymmetric dimers stacked along the a axis.

RESUMEN

The asymmetric unit of the title compound, C(18)H(16)N(2)O(2), contains two independent mol-ecules (A and B). In mol-ecule A, the pyrazole ring is inclined at angles of 48.86 (6) and 60.80 (6)° with respect to the two phenyl rings; the corresponding angles for mol-ecule B are 46.86 (6) and 58.63 (6)°. In the crystal, mol-ecules of type A are linked into sheets parallel to (001) via weak C-H⋯O hydrogen bonds, whereas the mol-ecules of type B are linked into chains along [010] via weak C-H⋯O hydrogen bonds.

RESUMEN

The title mol-ecule, C(11)H(12)N(2)OS(2), is twisted with a dihedral angle of 83.63 (12)° between the 1,3,4-thia-diazole and benzene rings. The meth-oxy group deviates slightly from the attached benzene ring, with a C-C-O-C torsion angle of 4.2 (4)°. In the crystal, mol-ecules are linked by weak C-H⋯N inter-actions and stacked along the c axis.

RESUMEN

In the title compound, C(8)H(8)N(4), the dihedral angle between the triazole ring [maximum deviation = 0.003 (1) Å] and the benzene ring is 34.57 (7)°. In the crystal, mol-ecules are linked into sheets lying parallel to the ac plane via inter-molecular N-H⋯N and C-H⋯N hydrogen bonds. Aromatic π-π [centroid-centroid distance = 3.6750 (8) Å] stacking and N-H⋯π inter-actions are also observed.

RESUMEN

The mol-ecule of the title thia-diazole derivative, C(11)H(11)N(3)O(2)S(2), has a butterfly-like structure and the whole mol-ecule is disordered with a site-occupancy ratio of 0.629 (4):0.371 (4). The mol-ecule is disordered in such a way that the 3-methyl-4-nitro-phenyl units of the major and minor components are approximately related by 180° rotation around the C-N bond axis. The dihedral angle between the 1,3,4-thia-diazole and benzene rings is 70.8 (4)° in the major component and 74.9 (6)° in the minor component. In the crystal, mol-ecules are arranged into screw chains along the c axis. These chains are stacked along the b axis. Weak inter-molecular C-H⋯O and C-H⋯π inter-actions and a short C⋯O contact [3.005 (7) Å] are present.

RESUMEN

In the title compound, C(11)H(15)N(3)O(3), one of the methyl groups attached to the benzamide unit is slightly twisted with a C-N-C-C torsion angle of 4.04 (13)°. The crystal packing is stabilized by weak intermolecular C-H⋯O hydrogen bonds together with a weak C-H⋯π inter-action.

RESUMEN

In the title compound, C(16)H(11)F(4)N(3)S, the dihedral angles between the thia-diazole ring and the difluorobenzyl rings are 81.95 (7) and 81.96 (7)°, whereas the dihedral angle between the difluorobenzyl rings is 11.41 (7)°. In the crystal structure, C-H⋯N and C-H⋯F inter-actions link the mol-ecules into two-dimensional arrays parallel to the bc plane.

RESUMEN

The asymmetric unit of the title compound, C(8)H(7)Br(2)NO(3), comprises two crystallographically independent mol-ecules (A and B). The nitro groups are twisted from the attached benzene rings, making dihedral angles of 39.26 (9) and 35.90 (9)° in mol-ecules A and B, respectively. In each mol-ecule, the dibromo-methyl group is orientated in such a way that the two Br atoms are tilted away from the benzene ring. An inter-esting features of the crystal structure is the two short Br⋯Br inter-actions which, together with inter-molecular C-H⋯O hydrogen bonds, link the mol-ecules into an extended three-dimensional network. The crystal structure is further stabilized by weak C-H⋯π inter-actions.