Synthesis and biological evaluation of novel urea, thiourea and squaramide diastereomers possessing sugar backbone

Işılar Ö., BULUT A., Sahin Yaglioglu A., Demirtaş İ., Arat E., Türk M.

Carbohydrate Research, vol.492, 2020 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 492
  • Publication Date: 2020
  • Doi Number: 10.1016/j.carres.2020.107991
  • Journal Name: Carbohydrate Research
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, BIOSIS, CAB Abstracts, Chimica, Compendex, EMBASE, Food Science & Technology Abstracts, MEDLINE, Veterinary Science Database
  • Keywords: Antiproliferative activity, Cytotoxicity, Squaramide, Sugar, Thiourea, Urea
  • Ondokuz Mayıs University Affiliated: No

Abstract

A series of novel chiral 14 urea, thiourea and squaramide stereoisomers possessing carbohydrate backbones as well as amide functional groups was synthesized and characterized by their, 1H NMR, 13C NMR, FT-IR, HRMS, optical rotation, and melting points. Their antiproliferative activities were investigated against HeLa and PC3 cell lines. The compounds 9, 11 and 12 showed better activities at 25 μM against PC3 cell line with respect to the standard 5-fluorouracil (5-FU). Especially, the compounds 9 and 11 showed higher activities than the standard 5-FU even at low concentration (5 μM) against HeLa cell line. IC50 results also confirm these activities. The compounds 9, 10 and 11 have the IC50 values of 1.10 μM, 1.51 μM and 1.02 μM, respectively while 5-FU has 2.51 μM. Moreover, their cytotoxicity tests have proven that their viabilities were in between 50% and 100%.