Synthesis, solvent role, absorption and emission studies of cytosine derivative

N Elangovan; Natarajan Arumugam; Abdulrahman I Almansour; Shanty Mathew; Sinouvassane Djearamane; Ling Shing Wong; Saminathan Kayarohanam

doi:10.1016/j.heliyon.2024.e28623

Synthesis, solvent role, absorption and emission studies of cytosine derivative

Heliyon. 2024 Mar 26;10(7):e28623. doi: 10.1016/j.heliyon.2024.e28623. eCollection 2024 Apr 15.

Authors

N Elangovan¹, Natarajan Arumugam², Abdulrahman I Almansour², Shanty Mathew³, Sinouvassane Djearamane^{4

5}, Ling Shing Wong⁶, Saminathan Kayarohanam⁷

Affiliations

¹ Research Centre for Computational and Theoretical Chemistry, Anjalam, 621208, Musiri, Tiruchirappalli, Tamilnadu, India.
² Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
³ Department of Chemistry, St. Joseph's College Research Center, Shanthinagar, 560027, Bangalore, India.
⁴ Department of Allied Health Sciences, Faculty of Science, Universiti Tunku Abdul Rahman, Jalan Universiti, Bandar Barat, Kampar, 31900, Malaysia.
⁵ Biomedical Research Unit and Lab Animal Research Centre, Saveetha Dental College, Saveetha Institute of Medical and Technical Sciences, Saveetha University, Chennai, 602 105, India.
⁶ Faculty of Health and Life Sciences, INTI International University, Nilai, 71800, Malaysia.
⁷ Faculty of Bioeconomics and Health Sciences, University Geomatika Malaysia, Kuala Lumpur, 54200, Malaysia.

Abstract

The (E)-4-((4-hydroxy-3-methoxy-5-nitrobenzylidene) amino) pyrimidin-2(1H)-one (C5NV) was synthesized from cytosine and 5-nitrovanilline by simple straightforward condensation reaction. The structural characteristics of the compound was determined and optimized by WB97XD/cc-pVDZ basis set. The vibrational frequencies were computed and subsequently compared to the experimental frequencies. We investiated the electronic properties of the synthesized compound in gas and solvent phases using the time-dependent density functional theory (TD-DFT) approach, and compared them to experimental values. The fluorescence study showed three different wavelengths indicating the nature of the optical material properties. Frontier molecular orbital (FMO) and molecular electrostatic potential (MEP) analyses were conducted for the title compound, and electron localized functions (ELF) and localized orbital locators (LOL) were used to identify the orbital positions of localized and delocalized atoms. Non-covalent interactions (H-bond interactions) were investigated using reduced density gradients (RDGs). The objective of the study was to determine the physical, chemical, and biological properties of the C5NV. The molecular docking study was conducted between C5NV and 2XNF protein, its lowest binding energy score is -7.92 kcal/mol.

Keywords: Cytosine; DFT; Molecular docking; Synthesis; Topology.