Synthesis, characterization, molecular docking, DNA binding, cytotoxicity and DFT studies of 1-(4-methoxyphenyl)-3-(pyridine-3-ylmethyl)thiourea

• Synthesized molecule adopted syn-anti configuration around sulphur atom.
• IC50 value against MCF-7 Cell line was 160.97 μM.
• Docking energy of was found to be −7.41 kcal/mol.
• DNA binding constant was found to be 3.71 × 106 Lmol−1.

A new compound 1-(4-methoxyphenyl)-3-(pyridine-3-ylmethyl)thiourea was synthesized and structure of compound (3) was elucidated by FT-IR, 1H-NMR, and mass spectrophotometer. The computational quantum chemical studies of compound (3) like, IR, UV, NBO analysis were performed by DFT with B3LYP exchange-correlation functional in combination with 6–311++G(d, p) basis sets. The compound (3) adopted syn-anti-configuration around sulphur atom, possessing stablization relative energy -740715 kcal/mol. The chemical potential of compound (3) is −3.37 eV and chemical hardness is −2.33 eV. However, ionization and electron affinity of compound (3) are −5.70 eV and −1.04 eV. The compound (3) was docked with B-DNA (1BNA) and the binding energy was found to be -7.41 kcal/mol. The nitrogen atom of thiourea of compound (3) binds with O3 and O4 of cytosine of A strand of DNA having bond lengths (1.92 Å) and (1.74 Å) respectively Furthermore, DNA binding constant was performed by UV–visible spectrophotometer. The binding constant was found 3.71 × 106 Lmol−1. In order to assess cytotoxic nature of the lead compound, MTT-assay was performed against MCF-7 cell line and IC50 value of compound (3) was observed at 160.97 μ M. Theoretical studies revealed that they are good agreement with experimental results.

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