Synthesis and Characterization of Some New Coumarins with in Vitro Antitumor and Antioxidant Activity and High Protective Effects against DNA Damage

Molecules. 2016 Feb 22;21(2):249. doi: 10.3390/molecules21020249.

Abstract

Coumarins are naturally occurring oxygen heterocyclic compounds having multifarious medicinal properties, hence used as lead compounds for designing new potent analogs. The chromene butenoic acid 3 and the benzochromene butenoic acid 4 which are derived from the reaction of glyoxalic acid with 3-acetylcoumarin and 3-acetylbenzocoumarin, respectively, were reacted with different nitrogen and carbon nucleophiles to give new heterocyclic compounds. The structures of the prepared compounds were elucidated by IR, ¹H-NMR, and mass spectroscopy. Some of the newly prepared compounds were tested in vitro against a panel of four human tumor cell lines namely; hepatocellular carcinoma (liver) HepG2, colon cancer HCT-116, human prostate cancer PC3, and mammary gland breast MCF-7. Also they were tested as antioxidants. Almost all of the tested compounds showed satisfactory activity.

Keywords: antioxidant activity; antitumor activity; functionalized coumarin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / therapeutic use
  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry*
  • Antioxidants / therapeutic use
  • Benzopyrans / chemistry
  • Coumarins / chemical synthesis
  • Coumarins / chemistry*
  • Coumarins / therapeutic use
  • DNA Damage / drug effects
  • Glyoxylates / chemistry
  • Hep G2 Cells
  • Humans
  • Neoplasms / drug therapy*
  • Oxidation-Reduction
  • Proton Magnetic Resonance Spectroscopy

Substances

  • Antineoplastic Agents
  • Antioxidants
  • Benzopyrans
  • Coumarins
  • Glyoxylates
  • glyoxylic acid