RESUMO
A highly stereoselective, three-component method has been developed to synthesize pyrrolidine and pyrrolizidine containing spirooxindole derivatives. The interaction between the dipolarophile α,ß-unsaturated carbonyl compounds and the dipole azomethine ylide formed in situ by the reaction of 1,2-dicarbonyl compounds and secondary amino acids is referred to as the 1,3-dipolar cycloaddition reaction. The reaction conditions were optimized to achieve excellent stereo- and regioselectivity. Shorter reaction time, simple work-up and excellent yields are the salient features of the present approach. Various spectroscopic methods and single crystal X-ray diffraction examinations of one example of compound 6i validated the stereochemistry of the expected products. The anti-diabetic activity of the newly synthesized spirooxindole derivatives was tested against the α-glucosidase and α-amylase enzymes. Compound 6i was found to exhibit potent inhibition activity against α-glucosidase and α-amylase enzymes which is further evidenced by molecular docking studies.
RESUMO
In this study, theoretical harmonic vibrational frequencies and geometric parameters of N-(4-methoxybenzoyl)-2-methylbenzenesulfonamide have been investigated by Hartree-Fock (HF), density functional theory (B3LYP hybrid functional) methods with 6-311++G (d,p) basis set, for the first time. Experimental FT-IR (400-4000cm(-1)) and Laser-Raman spectra (100-4000cm(-1)) of title compound in solid phase have been recorded. Interaction energies, N-Hâ¯O hydrogen bonds, C-Hâ¯O and aromatic πâ¯π stacking interactions in dimer structures of the title compound have been evaluated by the calculation methods. The dimer calculations have aimed to present the efficacy and performance of M06-2X hybrid functional on the intermolecular interactions and more strongly bound systems for the corrected and interaction energy by the counterpoise correction procedure. The interaction energies by M06-2X approach give more stable results than HF and B3LYP, extremely. The more strongly bonds, especially, on N-Hâ¯O hydrogen bonds and πâ¯π interaction for the both dimer structure have also supported that the M06-2X functional of density functional is more effective.
Assuntos
Derivados de Benzeno/química , Sulfonamidas/química , Dimerização , Ligação de Hidrogênio , Modelos Moleculares , Teoria Quântica , Espectroscopia de Infravermelho com Transformada de Fourier , Análise Espectral RamanRESUMO
In the title compound, C16H8F6N2, the dihedral angle between the pyrazole and di-fluoro-benzene rings is 50.30â (13)°, while those between the pyrazole and fluoro-benzene rings and between the di-fluoro-benzene and fluoro-benzene rings are 38.56â (13) and 53.50â (11)°, respectively. Aromatic π-π stacking inter-actions between adjacent di-fluoro-benzene rings [centroid-centroid separation = 3.6082â (11)â Å] link the mol-ecules into dimers parallel to [21-2].
RESUMO
In the title compound, C18H21F3N4O4, the piperazine ring adopts a chair conformation and the dihedral angle between the oxa-diazole and benzene rings is 6.45â (14)°. The C atoms and their attached H atoms in the piperazine ring are disordered, with site-occupation factors of 0.576â (12) and 0.424â (12). In the crystal, mol-ecules are linked through weak C-Hâ¯O inter-actions, generating an R 2 (2)(12) motif. Further, secondary C-Hâ¯O inter-molecular inter-actions link the mol-ecules into C(6) chains along [100].
RESUMO
In the title compound, C15H15NO4S, the dihedral angle between the benzene rings is 78.62â (16)°. In the crystal, adjacent mol-ecules are linked along the c axis into C(4) chains through strong N-Hâ¯O hydrogen bonds. Mol-ecules are further connected through C-Hâ¯O hydrogen bonds into a hexa-meric unit generating an R (6) 6(66) motif. Another C-Hâ¯O inter-action connects the mol-ecules along the c axis, forming C(5) chains. A region of disordered electron density, most probably disordered methanol-water solvent mol-ecules, was treated with the SQUEEZE routine in PLATON [Spek (2009 â¶). Acta Cryst. D65, 148-155]. The formula mass and unit-cell characteristics do not take into account this disordered solvent.
RESUMO
In the title sulfonamide derivative, C11H10ClN3O2S, the dihedral angle between the pyridine rings is 46.85â (12)°. The N atom of the chloro-pyridine ring is anti to the N-H bond. In the crystal, mol-ecules are linked through N-Hâ¯N hydrogen bonds into zigzag chains parallel to [001] with a C(7) graph-set motif.