5.6- Dimethylbenz acridines

In the dibenzacridine series, carcinogenicity appears to decrease in the order dibenz[c,/i]acridine > dibenz[a,/2]acridine > dibenz[a J]acridine, with all compounds being less active than the monomethyl- and dimethylbenz[ ]acridines. Addition of K-region alkyl substituents will generally enhance carcinogeni-... 

Aminoazotoluene 7-10-Dimethylbenz[c]acridine Diazoacetylglycine ethyl ester... 

In another study reported by Wynder and Hoffmann (4317), mouse skin was initiated with a single application of 300 Xg of 7,12-dimethylbenz[a]anthracene and then painted with a 0.5% solution of dibenz[a,/ acridine, three times weekly. The same tumor response was observed as with dibenz[a,y ]acridine alone except that the tumors appeared 2 to 3 months earlier. The investigators interpreted this finding as indicating ... 

Benz[a]acridine 10-Methylbenz[a]acridine Benz[c]acridine 12-Methylbenz[a]acridine 10-Methylbenz[c Jacridine 8-Methylbenz[c]acridine 10,11-Dimethylbenz[c]acridine 8,9,12-Trimethylbenz[a]acridine 9,12>Dimethylbenz[a]acridine 8.12- Dimethylbenz[a]acridine 7.11- Dimethylbenz[c]acridine 8.10.12- Trimethylbenz[a]acridine 7,10-Dimethylbenz[c]acridine 7,9-Dimethylbenz[c]acridine 7.9.11- Trimethylbenz[c]acridine 7.8.9.11- Tetramethylbenz[c]acridine... 

The retention characteristics of 29 aza-arenes (e.g., pyridine, acridine, quinoline, benz[a]acridine, and numerous substituted analogs) were studied on a diol column using a 97.5/2.5 iso-octane/ethanol mobile phase [611]. Dimethylbenz[a]acridine was least retained k < 3) and indole had the greatest retention (k > 9). The study also worked with 29 phenols (e.g., numerous alkyl-substituted phenols, nitrophenols, and halogenated phenols). They were studied in detail on the diol column using a 50/50 iso-octane/dichloromethane mobile phase. Appropriate selection of solvent composition provided baseline resolution of isomeric groups (e.g., dimethylphenols using hexane/ethyl acetate). 

Metabolites of 7,9- and 7,10-dimethylbenz[c]acridine (e.g., 7-[hydroxymethyl]-9-mediylbenz[c]acridine, 7,9-ditnethylbenz[c]acridine-5,6-oxide) were separated in 80 min using a silica column (A = 270 nm) and 95/5 petroleum ether/ethanol or 90/10 petroleum ether/ethyl acetate, respectively. At least 23 metabolites were positively identified [621], The retention behavior of benz[c]acridines and 11 methyl, dimethyl, and trimethyl analogs were studied on silica and aminopropyl columns [622]. Individual solute retention times were tabulated. For the silica column a 95/5 hexane/ethanol mobile phase was used and retention times ranged fiom 2.5 to 33 min. Incomplete resolution of three isomers resulted. Hexane and the aminopropyl column produced retention times of 8-26 min with at least partial resolution obtained for all isomers. 

Six hq>atic metabolites of 7,9- and 7,10-dimethylbenz[c]aaidine (e.g., 7-[hydro-xymethyl]-10-methylbenz[c]acridine, 7,9-dimethylbenz[c]aciidine-5,6-oxide) were separated from the parent compounds on a C,g column (A = 270nm) using a complex 80-min 24/76 - 100/0 acetonitrile/water gradient [621]. Analytes eluted from 35 min to 75 min. Peak shapes were excellent, even at the long r ention times. Peaks of interest were well separated from other extracted compounds. 

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