Science of Synthesis

Prager, R. H.; Williams, C. M., Science of Synthesis, (2005) 15, 987.

Acridine (‌1‌, dibenzo[b,e]pyridine; also previously known as benzo[b]quinoline or 10-azaanthracene; ‌Scheme 1‌) is a stable crystalline base, first isolated from coal tar by Graebe in 1870.[‌1‌] Some 40 years later, Browning discovered antibacterial activity in certain amino­acridines,[‌2‌] which led to the identification of antimalarial properties in other ­acridines, such as atebrin.[‌3‌] Dyestuffs based on acridines have been known since the early 20th century. Acridines are recognized as intercalating agents for DNA,[‌4‌] and nitracrine and amsacrine are undergoing clinical trials as antitumor agents.[‌5‌] Because of their cytotoxicity and antitumor activity,[‌8‌] there has been a growing interest in polycyclic aromatic alkaloids based on the pyrido[k,l]acridine skeleton, isolated from sponges or tunicates.[‌6‌,‌7‌] In addition, some of these compounds have antimalarial[‌9‌] and anti-HIV activities.[‌10‌] Acridines and acridinium salts are highly fluorescent,[‌11‌,‌12‌] and acridine-9-carboxylic acid derivatives have been shown to be useful in chemiluminescence assays for glucose oxidase alkaline phosphatase activities.[‌13‌]

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References

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• 8.Meeeee-Meee, (8888) M 8e, 888.