Abstract
An indazole derivative, 1-(3-amino-4-morpholino-1H-indazole-1-carbonyl)-N-phenylcyclopropa ne-1-carboxamide (C22H23N5O3, Mr = 405.45) has been synthesized by condensation of 1-(phenylcarbamoyl)cyclopropane-1-carboxylic acid with 4-morpholino-1H-indazol-3-amine, which was prepared from 2,6-difluorobenzonitrile by amination with morpholine and then cyclisation with hydrazine hydrate. Spectro-elemental characterizations and single-crystal X-ray analysis were done for the structure elucidation. C22H23N5O3 has a monoclinic system, space group P21/c with a = 10.427(2) Å, b = 17.283(4) Å, c = 13.759(2) Å, α = 90°, β = 122.773(12) °, γ = 90°. The optimized geometric bond lengths and bond angles obtained by using density functional theory (DFT) have been compared with X-ray diffraction values. The calculated HOMO - LUMO energy gap and electrostatic potential map were computed by DFT and reaction sites in the molecule are represented in molecular electrostatic potential maps (MEP) plot. The molecular electrostatic potential (MEP) surface map of the related molecule were investigated with theoretical calculations at the B3LYP/6-31G(d,p) levels. A quantitative analysis of the intermolecular interactions in the crystal structures has been performed using Hirshfeld surface analysis. In addition, the compound possesses distinct effective inhibition on the proliferation of HT-29, K562 and MKN45 cancer cell lines.
Published Version
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