Synthesis, antioxidant effectiveness, and docking study of new benzothiazolyl-chromenone-based fluorophores

Luminescence. 2023 Aug;38(8):1485-1492. doi: 10.1002/bio.4530. Epub 2023 Jun 10.

Abstract

As chromenones demonstrate significant push-pull fluorescence effects on the development and description of novel push-pull fluorescent compounds based on chromenone with exceptional molar extinction coefficients, benzothiazolyl-chromenone-based fluorophores were created by refluxing ethanol/piperidine over Knoevenagel's condensation. Many spectral methods, including 1 H-NMR, FT-IR analysis, and (C, H, N) analysis, were used to demonstrate the molecular structures of the synthesized benzothiazolyl-chromenone-based fluorophores. The synthesized fluorophore UV-vis absorption and emission spectra showed significant extinction coefficients, which were observed to be influenced by the substituted benzothiazole bridge in conjugation with the alkoxy donor moiety. It was discovered that the alkoxyl group-bonded substituents had an effect on the maximum absorbance wavelength. The benzothiazolyl-chromenone hybrid achieved antioxidant efficacy that compared favourably with commonly used medications [butylated hydroxytoluene (BHT) and vitamin C]. In contrast with the other hybrids, hybrid 3c, which has a hexyloxy tail, made good claims about its suitable action towards vitamins and reference medications. Additionally, the synthesized benzothiazolyl-chromenone-based hybrids showed marked coordination with antioxidant efficacy when docked studies of the hybrids towards the chosen 3NM8 protein were conducted.

Keywords: antioxidant; chromenone-based fluorophores; condensation; docking; p-alkoxy-salicylaldehyde.

MeSH terms

  • Antioxidants* / chemistry
  • Fluorescent Dyes*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Spectroscopy, Fourier Transform Infrared

Substances

  • Antioxidants
  • Fluorescent Dyes