Synthesis of Novel Spiro-Tetrahydroquinoline Derivatives and Evaluation of Their Pharmacological Effects on Wound Healing

Int J Mol Sci. 2021 Jun 10;22(12):6251. doi: 10.3390/ijms22126251.

Abstract

A highly diastereoselective method for the synthesis of novel spiro-tetrahydroquinoline derivatives is reported here, using a one-pot reaction method. All compounds were characterized by 1H-nuclear magnetic resonance (NMR) and mass spectroscopy, and their stereo configurations were confirmed by X-ray analysis. These activities of these derivatives were then tested in human keratocyte cells. The responses of cells to treatment with selected compounds were studied using scratch analysis, and the compounds were tested in a mouse excision wound model. Three of the derivatives demonstrated significant wound-healing activities.

Keywords: 1,3-indandione; one-pot reaction; spiro-tetrahydroquinoline; tetrahydroquinoline; wound healing.

MeSH terms

  • Animals
  • Humans
  • Keratinocytes / cytology
  • Keratinocytes / drug effects*
  • Male
  • Mice
  • Mice, Inbred C57BL
  • Models, Molecular
  • Quinolines / chemistry*
  • Spiro Compounds / chemistry
  • Spiro Compounds / pharmacology*
  • Stereoisomerism
  • Wound Healing / drug effects*

Substances

  • Quinolines
  • Spiro Compounds
  • 1,2,3,4-tetrahydroquinoline