Conformational profile, vibrational assignments, NLO properties and molecular docking of biologically active herbicide1,1-dimethyl-3-phenylurea

Heliyon

S.A. Popoola¹  Renjith Thomas²  K. Haruna³  M.S. Roxy⁴  Y. Sheena Mary⁵  A.A. Al-Saadi⁶  Veena S. Kumar⁶ 

[1] Corresponding author.;Department of Chemistry, Islamic University of Madinah, MadinahMunawara, Saudi Arabia;Department of Chemistry, King Fahd University of Petroleum and Minerals, Dhahran, Saudi Arabia;Department of Chemistry, St. Berchmans College (Autonomous), Changanacherry, Kerala, India;Department of Physics, Fatima Mata National College(Autonomous), Kollam, Kerala, India;Department of Physics, SN College, Kollam, Kerala, India;

关键词: Organic chemistry;    Pharmaceutical chemistry;    Theoretical chemistry;    DFT;    Fenuron;    Molecular docking;   

DOI  :  

来源: DOAJ

【 摘 要 】

1,1-Dimethyl-3-phenylurea (known as fenuron) which is a phenyl urea-based widely used herbicide exhibits interesting structural and conformational properties and a notable biological activity. A detailed analysis on the vibrational, molecular and electronic characteristics of fenuron has been carried out. Potential energy scans (PESs) performed at the B3LYP/6-311++G(d,p) level of theory predicted two possible minima corresponding to the optimized anti and synforms resulting from the internal rotation about the N-C bond. The presence of an auxochrome together with the interaction with DMSO solvent exhibited a blue shift corresponding to the C=O orbitals. Delocalization of HOMO and LUMO orbital facilitated the charge transfer effect in the molecule. The calculated HOMO-LUMO energies, chemical potential, energy gap and global hardness suggested a low softness value for the compound while its biological activity was described by the value of electrophilicity. Chlorine substitution in the phenyl ring influenced the orbital delocalization for ortho and para substitutions but that of meta remained unaffected. NLO properties were noticed to increase due to chlorine substitution in the parent molecule. The docking results suggested that the compound exhibits an inhibitory activity against mitochondrial ubiquinol-cytochrome-c reductase and can be developed as a potential anticancer agent.

【 授权许可】

Unknown