Chemical Properties
Light Pink Solid
Uses
An anticancer drug, showed strong activity against various murine tumors. A Camptothecin (CPT) derivative as antineoplastic agent against drug-resistant tumors. Irinotecan USP Related Compound E.
Definition
ChEBI: 7-ethylcamptothecin is a pyranoindolizinoquinoline.
Biological Activity
7-Ethylcamptothecin is one of the camptothecin analogs. Camptothecin (CPT), a cytotoxic alkaloid isolated from camptothecin analogues, has strong antitumor activity against L1210 leukemia and Walker 256 carcinosarcoma models.
Synthesis
To a 5L reactor were added 80 g of (S)-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione (camptothecin), 840 g of glacial acetic acid, and 368 g of concentrated sulfuric acid, and mechanical stirring was initiated until complete dissolution. Subsequently, 80 g of propionaldehyde was slowly added and 102 g of hydrogen peroxide was added dropwise. The reaction temperature was controlled in the range of -5 to 5°C for 10 minutes. After completion of the reaction, 10 kg of pure water was added to the system and stirring was continued for 2 hours. The precipitate was collected by filtration to give 72.5 g of (S)-4,11-diethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolo[1,2-b]quinoline-3,14(4H,12H)-dione (7-ethylcamptothecin) in 95.4% yield.
References
[1] Patent: CN108484624, 2018, A. Location in patent: Paragraph 0031; 0039; 0043; 0044
[2] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 6, p. 1446 - 1454
[3] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 10, p. 2574 - 2580
[4] Patent: WO2006/16203, 2006, A1. Location in patent: Page/Page column 9-10
[5] European Journal of Pharmaceutical Sciences, 2018, vol. 123, p. 546 - 559
