This submission belongs to the session a. General Organic Synthesis of the event The 4th International Electronic Conference on Synthetic Organic Chemistry
Published date
11 Sep, 2000
Citation
Yoel Kashman, Marta Garcia Gravalos, Amira Rudi, Avi Koller, Synthesis And Electrophilic Substitution of Pyrido[2,3,4-kl]acridines, in Proceedings of The 4th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2000, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-4-01809
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Synthesis And Electrophilic Substitution of Pyrido[2,3,4-kl]acridines
Avi Koller 1
Amira Rudi 1
Marta Garcia Gravalos 2
Yoel Kashman 1
1. School of Chemistry, Tel Aviv University, Ramat Aviv 69978, Israel
2. PharmaMar, Tres- Cantos, Madrid, Spain
Abstract
Several new pyrido[2,3,4-kl]acridines were synthesized by reacting naphthoquinone, juglone and cyclohexan-1,3-dione with b,b’-diaminoketones in a biomimetic reaction. The structure of all new compounds (6a, b, 8, 10, 11, 12, 14, 15, 16, 17a, b, 20, 21) was elucidated by NMR and MS spectroscopy. Elecrophilic substitution, mainly nitration, of the various compounds was undertaken and the substitution positions determined. A series of derivatives were prepared and their cytotoxicity towards P-388 mouse lymphoma cells analysed. The most cytotoxic derivatives were found to have IC50’s of 0.1 ug/ml.