Synthesis of an unusual quinazoline alkaloid: theoretical and experimental investigations of its structural, electronic, molecular and biological properties

An unusual quinazoline alkaloid (1) was obtained when 2-aminobenzaldehyde was refluxed with pyrrolidine in ethanol for 12 h. The synthesized compound was characterized using spectral data analysis augmented with X-ray and literature precedent. Single crystal analysis depicted four conformations differing slightly in bond angles and bond lengths. Compound 1 crystallizes in a triclinic crystal system with a P1̄ space group having two molecules within the unit cell. The experimentally obtained parameters were compared to those obtained theoretically, which depicted a good agreement. Using the DFT/B3LYP/6-31G (d,p) level of theory, HOMO–LUMO energy gap, molecular electrostatic potential (MEP), vibrational (IR) and NMR analyses were carried out. The HOMO–LUMO energy gap allowed the calculation of chemical hardness, chemical inertness, electronegativity and the electrophilicity index of the molecule, which depicted its potential kinetic stability and reactivity. Prediction of activity spectra of the target compound revealed that compound 1 possesses notable antineoplastic activity with P(a) = 0.884. The molecule was therefore evaluated against various cancerous cell lines in an in vitro SRB assay which depicted that compound 1 possesses the highest growth inhibition activity against THP-1 cell lines with an IC(50) of 7 μM.