Synthesis of novel salicylic acid-pyrrolone conjugates and investigation of their cytotoxic and genotoxic effects in Allium cepa root tip cells


GÜMÜŞ M. , CAN S., EROĞLU H. E. , KOCA İ.

Organic Communications, vol.14, no.3, pp.280-293, 2021 (Journal Indexed in ESCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 14 Issue: 3
  • Publication Date: 2021
  • Doi Number: 10.25135/acg.oc.111.21.06.2118
  • Title of Journal : Organic Communications
  • Page Numbers: pp.280-293
  • Keywords: Salicylic acid, pyrrolone, hybrid compound, diastereotopic proton, chromosome, mitotic index, SUBSTITUTED PYRROLIN-4-ONES, CHROMOSOME-ABERRATION, DERIVATIVES, 2(3H)-PYRROLONES, 2(3H)-FURANONES, CYCLIZATION, SCAFFOLD, CYCLE

Abstract

In the 20th century, many new drugs have been designed and synthesized to be used for therapeutic purposes. In these syntheses, especially the salicylic acid group is included in the structure of many drugs. The salicylic acid molecule is the starting material of aspirin and is a structurally important compound. There are many commercial products on the market that are synthesized from salicylic acid or contain salicylic acid group. In this study, the synthesis of salicylic acid-pyrrolone hybrid compounds was carried out from the reactions of furan-3-one compounds with 4-aminosalicylic acid and 5-aminosalicylic acid reagents. The synthesis reactions were achieved in three steps and in these synthesis, biologically active pyrrolone and salicylic acid groups were integrated. The characterizations of these compounds that were purified by column chromatography and crystallization method were made by FTIR, NMR and HRMS techniques. The cytotoxic and genotoxic potentials of the novel compounds (7a-e) were evaluated at five different concentrations (6.25, 12.5, 25, 50 and 100 mu M) using the Allium test system. As a result of cytogenetic analysis, it was determined that high concentrations of some hybrid compounds significantly reduced the number of divisions of A. cepa cells (cytotoxicity in 7a and 7c) and caused chromosomal abnormalities in dividing cells (genotoxicity in 7a, 7c, 7e, and especially 7d).