An experimental and computational study of pyrimidine based bis-uracil derivatives as efficient candidates for optical, nonlinear optical, and drug discovery applications

Abstract

Three novel pyrimidine based bis-uracil derivatives 1–3 were synthesized by the condensation reaction of 2-hydroxynaphthaldehyde with 6-amino-1,3-dimethylpyrimidine-2,-4(1H, 3H)-dione; 6-amino-1, 3-diethylpyrimidine-2,-4(1H, 3H)-dione, and 6-amino-1,-ethyl-3-methylpyrimidine-2,-4(1H, 3H)-dione, respectively and structurally characterized. The preliminary test of compounds was evaluated by SwissADME that can predict rapidly key parameters for a collection of molecules to support their drug discovery endeavors. Antimicrobial, photoluminescence, and molecular docking of compounds were also studied. The kinetic and thermal stabilities along with intramolecular charge transfer characters were obtained for compounds using frontier molecular orbitals, electrostatic potential diagrams as well as their orbital energies. Additionally, we applied state-of-art computational methods to assess the linear and nonlinear optical (NLO) properties of compounds at M06/6-311G** levels of theory. The third-order NLO properties of 1–3 were observed larger as compared to the standard indicating the considerable NLO character of all molecules, which may render the above derivatives as efficient candidates for NLO device fabrications.

Graphical Abstract

Keywords:

• Bis-uracil derivatives
• molecular docking
• NLO applications
• preliminary test
• SwissADME web tool

Acknowledgments

Author thanks the Sophisticated Analytical Instrument Facility (SAIF), IIT Madras for single crystal data collection of compound 1. We thank the Head, Department of Chemistry, NIT Patna and SAIF, IIT Patna for making available FT-IR and UV-Vis, and NMR spectral facility, respectively. The authors from the King Khalid University, Saudi Arabia acknowledge the financial and technical support from Research Center for Advanced Material Science at King Khalid University.

Disclosure statement

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Additional information

Funding

Financial assistance was received from the Council of Scientific and Industrial Research, New Delhi, India [01(2856)/16/EMR-II] is gratefully acknowledged. B. Mohan is thankful to CSIR, New Delhi, India for JRF fellowship (01(2856)/16/EMR-II). The authors from King Khalid University acknowledge the financial support from Research Center for Advanced Material Science (RCAMS) at King Khalid University for funding the work through grant number RCAMS/KKU/014-20.