Journal
MOLECULES
Volume 27, Issue 23, Pages -Publisher
MDPI
DOI: 10.3390/molecules27238112
Keywords
pyrido[3; 2; 1-de]phenanthridin-6-ones; N-aryl-N-(2-bromobenzyl) cinnamamides; intramolecular Friedel-Crafts alkylation; catalyzed direct C-H arylation; in silico computational methods; zebrafish embryos toxicity
Funding
- Colombian institute for science (Colciencias) [007-2017, 110274558597]
- RUDN University Scientific Projects Grant System [025233-2-000]
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A rapid and efficient synthesis of novel pyrido[3,2,1-de]phenanthridin-6-ones is reported, and the toxicological profile of the prepared compounds is explored.
A rapid, efficient, and original synthesis of novel pyrido[3,2,1-de]phenanthridin-6-ones is reported. First, the key cinnamamide intermediates 8a-f were easily prepared from commercial substituted anilines, cinnamic acid, and 2-bromobenzylbromide in a tandem amidation and N-alkylation protocol. Then, these N-aryl-N-(2-bromobenzyl) cinnamamides 8a-f were subjected to a TFA-mediated intramolecular Friedel-Crafts alkylation followed by a Pd-catalyzed direct C-H arylation to obtain a series of potentially bioactive 4-phenyl-4,5-dihydro-6H,8H-pyrido[3,2,1-de]phenanthridin-6-one derivatives 4a-f in good yields. Finally, the toxicological profile of the prepared final compounds, including their corresponding intermediates, was explored through in silico computational methods, while the acute toxicity toward zebrafish embryos (96 hpf-LC50, 50% lethal concentration) was also determined in the present study.
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