Carcinogenic nitrogen compounds. Part LVI. Benz[c]acridines and benzo[a]carbazoles methylated on the K-zone

Abstract

A number of benz [c]acridines and dibenz[a,h]-and dibenz[c,h] -acridines bearing a methyl substituent in a mesophenanthrenic region (K-zone) have been synthesised, and similarly-built polycyclic carbazoles methylated in the same region have been obtained from 3-methyl-1 -tetralone.AS in the benz[a]anthracene series,2 the site of methyl substitution that is the most favourable for carcinogenicity in the benz[c]acridines is position 7; indeed, all the benz[c]acridines so far found to be carcinogenic bear a methyl or an ethyl group in that position. If a similar analogy exists between the two series in respect of positions 5 and 6, the pronounced activity of 5-and 6-benz[a] anthracene (especially as sarcomagens 4, suggests that 5-and 6-benz[c]acridines would also display some degree of activity. Some such compounds had already been tested and found a ~t i v e , ~ but these carried an additional alkyl group in position 7, and hence it was desirable to prepare 5-and 6-methylbenz[c]acridines

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

“…First examples of these systems, published mostly in the 1950s, were provided by Buu-Hoı̈ and Jacquignon ( 171.2 ), Kloetzel et al ( 171.4 ), Campbell and Temple ( 171.5 ), and Barret and Buu-Hoı̈ ( 171.7 – 8 ). In the following decade, the Buu-Hoı̈ group synthesized a range of other fluoranthene derivatives, 171.9 , 171.10 – 13 , 171.14 , and 171.15 , which were explored as potential carcinogens. Shenbor and co-workers reported several further [ b ]­fused derivatives containing oxazole ( 171.19 – 20 ), imidazole ( 171.21 and 171.22 ), and pyrylium ( 171.23 ) moieties.…”