A series of triazolylcoumarins was synthesized by the cycloaddition of acetylenic derivatives to azide in the presence of Cu(I) catalyst at room temperature. All the synthesized compounds were evaluated for their anti-microbial activity against Gram-positive (B. subtilis and S. aureus), Gram-negative bacteria (K. pneumonia and P. vulgaris) and human pathogenic fungi (C. tropicalis and C. krusei), with tetracycline and fluconazole as standards for anti-microbial and anti-fungal activity. Triazolylcoumarins exhibit anti-microbial activity against all the tested pathogens, which is further supported by molecular docking studies.
In the title compound, C13H10O3, two prop-2-ynyloxy groups are attached to the benzaldehyde ring at positions 2 and 6. The crystal packing features C—H⋯O interactions.
In the title compound, C27H20O2, the central benzene ring makes dihedral angles of 64.86 (7) and 70.35 (7)° with the methyl-substituted ring and the biphenyl ring system, respectively. The crystal packing is stabilized by intermolecular C—H⋯O interactions, which link the molecules into chains parallel to the b axis.
The crystal studied of the title compound, C19H14O2S, was an inversion twin with a 0.7 (1):0.3 (1) domain ratio. The central benzene ring makes dihedral angles of 63.31 (9) and 60.86 (9)°, respectively, with the 4-methylphenyl and thiophene rings. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds and S⋯π [3.609 (3) Å] interactions.
In the title compound, C21H16O, the dihedral angle between the anthracene ring system and the benzene ring is 74.3 (5)°. The anthracene ring system is essentially planar (r.m.s. deviation = 0.0257 Å) and the methoxy group lies in the plane of the benzene ring [C1—O1—C2—C7 torsion angle = 0.5 (2)°]. The crystal structure features π–π [centroid–centroid distance = 3.9487 (12) Å] and C–H⋯π interactions, forming a sheet running along the a-axis direction.
The asymmetric unit of the title compound, C10H8O3, contains two independent molecules, both of which are almost planar (r.m.s deviations for all non-H atoms of 0.044 and 0.053 Å). The dihedral angles between the benzene ring and the prop-1-yne group are 3.47 (1) and 3.07 (1)° in the two molecules, and the prop-1-yne groups adopt extended conformations. In each molecule, an intramolecular O—H⋯O hydrogen bond involving the OH and aldehyde substituents forms an S(6) ring. In the crystal, molecules are linked into cyclic centrosymmetric dimers via C—H⋯O hydrogen bonds, generating R
2
2(14) ring motifs. The crystal structure is further stabilized by aromatic π–π stacking interactions between the benzene rings [centroid–centroid distances = 3.813 (2) and 3.843 (2) Å]
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.