Benzofuran hydrazones as potential scaffold in the development of multifunctional drugs: Synthesis and evaluation of antioxidant, photoprotective and antiproliferative activity

Eur J Med Chem. 2018 Aug 5:156:118-125. doi: 10.1016/j.ejmech.2018.07.001. Epub 2018 Jul 2.

Abstract

New benzofuranhydrazones 3-12 were easily prepared and assayed for their radical-scavenging ability. Hydrazones 3-12 showed different extent antioxidant activity in DPPH, FRAP and ORAC assays. Good antioxidant activity is related to the number and position of hydroxyl groups on the arylidene moiety. High antioxidant activity is showed by the 2-hydroxy-4-(diethylamino)benzylidene derivative 11. Furthermore, hydrazones 3-12 showed photoprotective capacities with satisfactory in vitro SPF as compared to the commercial PBSA sunscreen filter. The antiproliferative effects of the hydrazones 3-12 was tested on erythroleukemia K562 and Colo-38 melanoma human cells. All the compounds showed growth inhibition in the micromolar to sub micromolar concentration range. If taken together these results points to benzofuran hydrazones as potential multifunctional molecules especially in the treatment of neoplastic diseases being the good antioxidant properties of 5, 7 and 11 correlated to their high antiproliferative activity.

Keywords: Antioxidant activity; Antiproliferative activity; Benzofuran hydrazones; Photoprotective agents; Polyhydroxylated compounds.

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry*
  • Antioxidants / pharmacology
  • Benzofurans / chemical synthesis
  • Benzofurans / chemistry*
  • Benzofurans / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Drug Design*
  • Humans
  • Hydrazones / chemical synthesis
  • Hydrazones / chemistry*
  • Hydrazones / pharmacology
  • Leukemia, Erythroblastic, Acute / drug therapy
  • Melanoma / drug therapy
  • Structure-Activity Relationship
  • Sunscreening Agents / chemical synthesis
  • Sunscreening Agents / chemistry*
  • Sunscreening Agents / pharmacology

Substances

  • Antineoplastic Agents
  • Antioxidants
  • Benzofurans
  • Hydrazones
  • Sunscreening Agents