Synthesis and anticancer activity of new [(Indolyl)pyrazolyl]-1,3,4-oxadiazole thioglycosides and acyclic nucleoside analogs

Nucleosides Nucleotides Nucleic Acids. 2017 Jul 3;36(7):474-495. doi: 10.1080/15257770.2017.1327665. Epub 2017 Jun 14.

Abstract

New [(Indolyl)pyrazolyl]-1,3,4-oxadiazole compounds and their derived thioglycosides as well as the corresponding sugar hydrazones were synthesized. The acyclo C-nucleoside analogs of the oxadiazoline base system were also prepared by reaction of acid hydrazides with aldehydo sugars followed by one pot process encompassing acetylation and cyclization of the synthesized hydrazones. The anticancer activity of the newly synthesized compounds was studied against colorectal carcinoma (HCT116), breast adenocarcinoma (MCF7) and prostate cancer (PC3) human tumor cell lines and a number of compounds showed moderate to high activities.

Keywords: C-Nucleosides; Indolyl(pyrazole); anticancer; oxadiazole; thioglycosides.

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / metabolism
  • Antineoplastic Agents / pharmacology*
  • Catalytic Domain
  • Cell Line, Tumor
  • Cyclin-Dependent Kinase 2 / chemistry
  • Cyclin-Dependent Kinase 2 / metabolism
  • Cyclization
  • Humans
  • Molecular Docking Simulation
  • Nucleosides / chemistry*
  • Oxadiazoles / chemistry*
  • Structure-Activity Relationship
  • Thioglycosides / chemical synthesis*
  • Thioglycosides / chemistry
  • Thioglycosides / metabolism
  • Thioglycosides / pharmacology*

Substances

  • Antineoplastic Agents
  • Nucleosides
  • Oxadiazoles
  • Thioglycosides
  • 1,3,4-oxadiazole
  • Cyclin-Dependent Kinase 2