Synthesis of Biologically Active Indenoisoquinoline Derivatives via a One-Pot Copper(II)-Catalyzed Tandem Reaction

2017/02/08 by Chia‐Yu Huang, Veerababurao Kavala, Chun-Wei Kuo +3 · 1 citation
Biochemistry, Genetics and Molecular Biology · Chemistry · #Cancer therapeutics and mechanisms #Synthesis and Biological Evaluation #Synthesis and bioactivity of alkaloids

paper · doi:10.1021/acs.joc.6b02814

openalex publication_date 2017/02/08 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/01

Abstract

A concise route for the synthesis of indenoisoquinoline derivatives from 2-iodobenzamide and 1,3-indanedione derivatives in the presence of copper(II) chloride and cesium carbonate in acetonitrile solvent is reported. A wide variety of 2-iodobenzamide derivatives and indandiones could be used to synthesize indenoisoquinoline derivatives and other fused indenoisoquinoline in moderate to good yields. This methodology was adapted for the one-step synthesis of a series of clinically active topoisomerase I inhibitors such as NSC 314622, LMP-400, LMP-776.

Citations

• Nitrated Indenoisoquinolines as Topoisomerase I Inhibitors: A Systematic Study and Optimization
• Convenient synthesis of indeno[1,2-c]isoquinolines as constrained forms of 3-arylisoquinolines and docking study of a topoisomerase I inhibitor into DNA–topoisomerase I complex
• Design, Synthesis, and Biological Evaluation of Indenoisoquinoline Topoisomerase I Inhibitors Featuring Polyamine Side Chains on the Lactam Nitrogen
• Synthesis and Evaluation of Indenoisoquinoline Topoisomerase I Inhibitors Substituted with Nitrogen Heterocycles
• Synthesis of New Indeno[1,2-c]isoquinolines: Cytotoxic Non-Camptothecin Topoisomerase I Inhibitors
• Inhibition of Topoisomerase (DNA) I (TOP1): DNA Damage Repair and Anticancer Therapy
• Design, docking, and synthesis of novel indeno[1,2-c]isoquinolines for the development of antitumor agents as topoisomerase I inhibitors
• Stereoselective oxidation by thionyl chloride leading to the indeno[1,2-c]isoquinoline system

Cited by

• Topoisomerase inhibitor [wikipedia]