Synthesis of Hybrid Phosphorated Indenoquinolines and Biological Evaluation as Topoisomerase I Inhibitors and Antiproliferative agents

María Fuertes, Asier Selas, Angela Trejo, Birgitta R. Knudsen, Francisco Palacios, Concepción Alonso
2021 Bioorganic & Medicinal Chemistry Letters  
This work describes the first synthesis of diethyl 6,6a,7,11b-tetrahydro-5H-indeno[2,1-c]quinolinylphosphonates 5, diethyl 7H-indeno[2,1-c]quinolinylphosphonates 6 and diethyl 7-oxo-7H-indeno[2,1-c]quinolinylphosphonates 7, which were prepared in good to high overall yields. The synthetic route involves a multicomponent reaction of 2-phosphonateaniline, aldehydes and indene as olefin and allows the selective generation of three stereogenic centres in a short, efficient and reliable manner. The
more » ... elective dehydrogenation of 1,2,3,4-tetrahydroindenoquinolines leads to the formation of corresponding indenoquinolines, and subsequent oxidation of methylene group of the indenoquinolines allows the access to indenoquinolinones.
doi:10.1016/j.bmcl.2021.128517 pmid:34952177 fatcat:2dv7srqzxrddjntun2tzs5w3ai