ABSTRACT
Three isatin derivatives, namely, 1-allyl-3-hydroxy-3-(6-oxocyclohex-1-en-1-yl)indolin-2-one, C17H17NO3, 1-ethyl-3-hydroxy-3-(6-oxocyclohex-1-en-1-yl)indolin-2-one, C16H17NO3, and 5-bromo-3-hydroxy-1-methyl-3-(6-oxocyclohex-1-en-1-yl)indolin-2-one, C15H14BrNO3, were synthesized, crystallized by the slow-evaporation technique, characterized by 1H and 13C NMR spectroscopy, and analysed by the single-crystal X-ray diffraction (XRD) method. Quantum chemical parameters, such as the energy of the highest occupied molecular orbital, energy of the lowest unoccupied molecular orbital, energy gap, electronic energy, ionization potential, chemical potential, global hardness, global softness and electrophilicity index, were calculated. The druglikeness and bioactivity scores of the compounds were calculated. The activities of these isatin derivatives against bacterial strains, such as Eschericia coli, Proteus vulgaris, Shigella flexneri, Staphylococcus aureus and Micrococcus luteus, and the fungal strain Aspergillus niger, were determined using the well-diffusion assay method. Molecular docking studies were carried out to predict the binding mode of the isatin compounds with the penicillin binding protein enzyme and to identify the interactions between the enzyme and the ligands under study.
Subject(s)
Isatin/chemistry , Isatin/chemical synthesis , Crystallography, X-Ray , Hydrogen Bonding , Isatin/analogs & derivatives , Ligands , Magnetic Resonance Spectroscopy , Molecular Docking Simulation , Quantum TheoryABSTRACT
The crystal structures of three chalcones with a bromo-substituted but-oxy side chain, viz. (E)-1-[4-(4-bromo-but-oxy)-phen-yl]-3-phenyl-prop-2-en-1-one, C19H19BrO2, (I), (E)-1-[4-(4-bromo-but-oxy)-phen-yl]-3-(4-meth-oxy-phen-yl)prop-2-en-1-one, C20H21BrO3, (II), and (E)-1-[4-(4-bromo-but-oxy)-phen-yl]-3-(3,4-di-meth-oxy-phen-yl)prop-2-en-1-one, C21H23BrO4, (III), are reported. In all mol-ecules, the conformation of the keto group with respect to the olefinic bond is s-cis. Mol-ecules of (I) and (II) are nearly planar, while mol-ecule (III) is not planar. In the crystal of compounds (I) and (II), mol-ecules are linked into chains parallel to the c axis by C-Hâ¯π inter-actions. In the crystal of compound (III), mol-ecules are linked by a pairs of C-Hâ¯O hydrogen bonds, forming inversion dimers. Weak C-Brâ¯π inter-actions are also observed in (III).
ABSTRACT
The title compound, C29H24N2OS, contains a pheno-thia-zine moiety linked to a planar carbazole unit (r.m.s. deviation = 0.029â Å) by a C-C single bond. The pheno-thia-zine moiety possesses a typical non-planar butterfly structure with a fold angle of 27.36â (9)° between the two benzene rings. The dihedral angle between the mean planes of the carbazole and pheno-thia-zine units is 27.28â (5)°. In the crystal, mol-ecules stack in pairs along the c-axis direction, linked by offset π-π inter-actions [inter-centroid distance = 3.797â (1)â Å]. There are C-Hâ¯π inter-actions present linking these dimers to form a three-dimensional structure.
ABSTRACT
In the title compound, C35H30N4O3, the spiro C atom connects the five-membered pyrrolidine ring and the indeno-quinoxaline ring system. The pyrrolidine ring adopts a twist conformation. An intra-molecular N-Hâ¯N inter-action between the amino group and the pyrazine ring is observed. In the crystal, mol-ecules are linked by a pairs of C-Hâ¯O hydrogen bonds, forming inversion dimers.
ABSTRACT
In the title compound, C36H31NO4, two spiro links connect the methyl-substituted pyrrolidine ring to the ace-naphthyl-ene and cyclo-hexa-none rings. The cyclo-hexa-none ring is further connected to the dioxalane ring by a third spiro junction. The five-membered ring of the ace-naphthylen-1-one ring system adopts a flattened envelope conformation with the ketonic C atom as flap, whereas the dioxalane and pyrrolidine rings each have a twist conformation. The cyclo-hexa-none ring assumes a boat conformation. Three intra-molecular C-Hâ¯O hydrogen bonds involving both ketonic O atoms as acceptors are present. In the crystal, C-Hâ¯O hydrogen bonds connect centrosymmetrically related mol-ecule into chains parallel to the b axis, forming rings of R 2 (2)(10)and R 2 (2)(8) graph-set motifs.
ABSTRACT
In the title compound, C36H29Cl2NO4, two spiro links connect the methyl-substituted pyrrolidine ring to the ace-naphthyl-ene and cyclo-hexa-none rings. The cyclo-hexa-none ring is further connected to the dioxalane ring by a third spiro junction. The five-membered ring of the ace-naphthylen-1-one ring system adopts a flattened envelope conformation, with the ketonic C atom as the flap, whereas the dioxalane and pyrrolidine rings each have a twist conformation. The cyclo-hexenone ring assumes a boat conformation. An intra-molecular C-Hâ¯O hydrogen-bond inter-action is present. In the crystal, mol-ecules are linked by non-classical C-Hâ¯O hydrogen bonds, forming chains extending parallel to the a axis.
ABSTRACT
In the title compound, [Fe(C5H5)(C34H28N3O)], the four-fused-rings system of the 11H-indeno-[1,2-b]quinoxaline unit is approximately planar [maximum deviation = 0.167â (4)â Å] and forms a dihedral angle of 37.25â (6)° with the plane of the benzene ring of the methyl-benzoyl group. Both pyrrolidine rings adopt a twist conformation. An intra-molecular C-Hâ¯O hydrogen bond is observed. In the crystal, mol-ecules are linked by C-Hâ¯O hydrogen bonds and weak C-Hâ¯π inter-actions, forming double chains extending parallel to the c axis.