Synthesis and Anticancer Activity of New 1-Thia-4-azaspiro[4.5]decane, Their Derived Thiazolopyrimidine and 1,3,4-Thiadiazole Thioglycosides

Molecules. 2017 Jan 20;22(1):170. doi: 10.3390/molecules22010170.

Abstract

New 1-thia-azaspiro[4.5]decane derivatives, their derived thiazolopyrimidine and 1,3,4-thiadiazole compounds were synthesized. The thioglycoside derivatives of the synthesized (1,3,4-thiadiazolyl)thiaazaspiro[4.5]decane and thiazolopyrimidinethione compounds were synthesized by glycosylation reactions using acetylated glycosyl bromides. The anticancer activity of synthesized compounds was studied against the cell culture of HepG-2 (human liver hepatocellular carcinoma), PC-3 (human prostate adenocarcinoma) and HCT116 (human colorectal carcinoma) cell lines and a number of compounds showed moderate to high inhibition activities.

Keywords: 1,3,4-thiadiazoles anticancer activity; 1-thia-azaspiro[4.5]decane; thiazolopyrimidine; thioglycosides.

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Carcinoma, Hepatocellular / drug therapy*
  • Cell Line, Tumor
  • Colorectal Neoplasms / drug therapy*
  • Glycosylation
  • HCT116 Cells
  • Hep G2 Cells
  • Humans
  • Liver Neoplasms / drug therapy*
  • Male
  • Prostatic Neoplasms / drug therapy*
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Spiro Compounds / pharmacology
  • Structure-Activity Relationship
  • Thiadiazoles / chemical synthesis
  • Thiadiazoles / chemistry
  • Thiadiazoles / pharmacology*
  • Thiazolidines / chemical synthesis*
  • Thiazolidines / chemistry
  • Thiazolidines / pharmacology
  • Thioglycosides / chemical synthesis
  • Thioglycosides / chemistry
  • Thioglycosides / pharmacology

Substances

  • Antineoplastic Agents
  • Spiro Compounds
  • Thiadiazoles
  • Thiazolidines
  • Thioglycosides
  • 1,3,4-thiadiazole