Synthesis, Structural Analysis and Antiproliferative Activity of Nitrogen-Containing Hetero Spirostan Derivatives: Oximes, Heterocyclic Ring-Fused and Furostanes


İlkar Erdağı S., Yıldız U.

CHEMISTRYSELECT, vol.7, no.24, 2022 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 7 Issue: 24
  • Publication Date: 2022
  • Doi Number: 10.1002/slct.202200439
  • Journal Name: CHEMISTRYSELECT
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier
  • Keywords: Antiproliferative activity, Diosgenin, Heterocyclic ring-fused, Nitrogen heterocycles, Steroidal oximes, BIOLOGICAL EVALUATION, CYTOTOXIC ACTIVITY, ANTITUMOR-ACTIVITY, ANTICANCER AGENTS, DESIGN, PREGNENOLONE, ANTIOXIDANT, THIOPHENE, SAPONINS
  • Kocaeli University Affiliated: Yes

Abstract

The present study focuses on the synthesis of spirostan derivatives as potential drug candidates for biological applications. Recently, spirostan derivatives containing the hetero-atom have attracted great scientific attention due to their anti-cancer, anti-diabetes, and anti-inflammatory properties. In this study, nitrogen-containing novel spirostan derivatives with substituted oxime, nitrile, pyrazole, isoxazole structures in ring-A and F were designed and synthesized starting from diosgenin. The intermediates and target derivatives' chemical structures were characterized by FTIR, HRMS, (HNMR)-H-1, (CNMR)-C-13, elemental analysis, and HPLC techniques. The target compounds were evaluated for their cytotoxicities in two human cancer cell lines (MCF-7 and A549). The tested compounds exhibited potent anticancer activity against human breast adenocarcinoma (MCF-7) and lung adenocarcinoma (A549). On the other hand, the toxicity of the tested compounds against human healthy fetal lung fibroblasts (MCR-5) indicated that compounds were non-toxic for the human body. The results showed that compounds may be used as a promising agents for anticancer agents with improved efficacy.