Organocatalytic cascade reaction for the asymmetric synthesis of novel chroman-fused spirooxindoles that potently inhibit cancer cell proliferation.

Abstract

The enantioselective preparation of pharmacologically interesting chroman-fused spirooxindole derivatives is described based on an organocatalytic multicomponent cascade reaction. The compounds synthesized using this method potently inhibited the proliferation of various cancer cell lines. The most potent compound (7e) induced caspase-independent apoptosis and cell cycle arrest in MCF-7 breast cancer cells by interfering with the p53-MDM2 interaction and downstream pathways.

• Authors: Rui Zhou, Qinjie Wu, Mingrui Guo, Wei Huang, Xianghong He, Lei Yang, Fu Peng, Gu He, Bo Han
• Journal: Chemical communications (Cambridge, England) (Chem Commun (Camb)) Vol. 51 Issue 66 Pg. 13113-6 (Aug 25 2015) ISSN: 1364-548X [Electronic] England
• PMID: 26186061 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antineoplastic Agents
• Chromans
• Indoles
• Tumor Suppressor Protein p53
• Proto-Oncogene Proteins c-mdm2

Topics

• Antineoplastic Agents (chemical synthesis, chemistry, metabolism, pharmacology)
• Apoptosis (drug effects)
• Catalysis
• Cell Cycle Checkpoints (drug effects)
• Cell Proliferation (drug effects)
• Chemistry Techniques, Synthetic
• Chromans (chemical synthesis, chemistry, metabolism, pharmacology)
• Humans
• Indoles (chemistry)
• MCF-7 Cells
• Models, Molecular
• Protein Conformation
• Proto-Oncogene Proteins c-mdm2 (chemistry, metabolism)
• Tumor Suppressor Protein p53 (metabolism)