期刊
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
卷 57, 期 -, 页码 -出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2021.128517
关键词
Indenoquinolinyl phosphonates; Topoisomerase I; Enzyme inhibition; Antiproliferative effect
资金
- Gobierno Vasco, Universidad del Pais Vasco (GV, UPV) [IT 992-16]
- Ministerio de Ciencia, Innovacion y Universidades (MCIU), Agencia Estatal de Investigacion (AEI) y Fondo Europeo de Desarrollo Regional (FEDER
- UE) [RTI2018-101818-B-I00]
This work describes the first synthesis of a series of indenoquinoline compounds and demonstrates a highly selective and efficient synthetic method. The synthetic route is concise, efficient, and reliable, providing a suitable pathway for the synthesis of indenoquinolinones with potential biological activities.
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]quinolinylphospho-nates 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 selective 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.
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