7- Methylbenz acridine

Nagano, M., and Yu H. (2003) Photoreaction of 9-Methylbenz[c]acridine with Diphenylacetic Acid in the Chiral Cocrystal, Heterocycles, 60, 2251-2258... 

Some methylbenz[c]acridines are strongly carcinogenic, whereas their derivatives are inactive [18-22]. Previously, we reported on the relationship between the carcinogenic activity of benz[a]acridines [30-40] and the zr-spin density [25] and the relationship between the carcinogenic activity of benz[a]acridines [30-41] and the values of the resonance energy per. v-elecIron (REPE) [26,27]. Consequently, by clockwise rotation on an angular ring or naphthalene moiety, the distribution of the zr-spin dens-... 

Chang RJ, Levin W, Wood AW, Shirai N, Ryan AJ, Duke CC, Jerina DM, Holder GM, Conney AH (1986) High tumorigenicity of the 3,4-dihydrodiol of 7-methylbenz[c] acridines on mouse skin and in newborn mice. Cancer Res 46 4552-4555... 

Other drugs studied by Moore et al. include chlorine containing photosensitizers (178), the effect of surfactants on photosensitizers (179), photosensitization by malarial drugs (180), nalidic and oxolinic acids (181), 6-mercaptopurine (182), azathioprine and nitroimidazole (183), 7-methylbenz[c]acridine and related products (184), naproxen, ben-oxaprofen and indomethacin (185), mefloquine (186), sulfamethoxazole and trimethoprim (187), benzydamine (188), photodecomposition of hydrochlorthiazide (189), tetracycline (190), frusemide (191), 6-mercaptopurine (192), 7-methylbenz[c]acridine (193), metronidazole, misonidazole and azathioprine (194), misonidazole and metronidazole (195), benzydamine (196), components in drug formulations (197) and sulfamethoxazole (198,199). 

Burt CD, Moore DE. Photochemical sensitization by 7-methylbenz[c]acridine and related compounds. Photochem Photobiol 1987 45 729-739. 

Burt CD, Cheung HT A, Holder G, Moore DE. Photooxidation of 7-methylbenz[c]acridine in methanol—identification of two primary photoproducts. J Chem Soc Perkin Trans 1986 1 741-745. 

Several routes to benz[c]acridines involve electrophilic aromatic substitution to form the heterocyclic ring. Thus, 9-nitrobenz[c]acridine results from the cyclisation of the 2-(l-naphtlylamino)benzaldehyde derived from 1-naphthylamine and 2-fluoro-5-nitrobenzaldehyde (J. Rosevear and J.F.K. Wilshire, Austral. J. Qiem., 1981, 34, 839). The reaction between a ff-aryl-l-naphthylamine and acetic anhydride has been used to synthesise 9- and ll-hydroxy-7-methylbenz[c]acridines and cyclisation of partially reduced 2-(l-naphtltylamino)benzoic acid by phosphorus oxychloride affords the 7-chloro-l,2,3,4-tetralydro derivative (B.V. Lap et ai,y J. heterocyclic Chem., 1983, 20, 281). 

Allylic bromination followed by dehydrobromination enables both 1,2,3,4- and 8,9,10,ll-tetrahydro-7-methylbenz[c]acridines to be converted into the respective dihydro derivative (C.C. Duke, P.T. hfcirphy and G.M. Holder, J. org. Chem., 1984, 4446). 

Metabolic oxidation of 7-methylbenz[c]acridine occurs at the methyl substituent and at the 1,2-, 5,6-, 8,9- and 10,11-positions (L.J. Boux et at.. Carcinogenesis, 1983, 4, 1429). Photo-oxidation of 7-methylbenz[c]acridine in methanol is complex, but the identified products involve reaction at the 5,6-position although not tia the epoxide this process is an alternative mechanism for the biological activation of the benzacridine (C.D. Burt et at., J. chem. Soc. Perkin I, 1986, 741). 

Irradiation of the enantiomorphous co-crystals obtained from mixed solutions of 9-methylbenz[c]acridine and diphenylacetic acid is reported to yield the photodecarboxylation-addition product (44) as essentially a racemic mixture, along with diphenylmethane and 1,2-tetraphenylethane. The lack of selectivity in the formation of (44) from the co-crystals is considered to arise from the molecular arrangement of the reactants in the lattice, and the same products are also formed from irradiation of the acridine and the acid in acetonitrile solution. 

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... 

Methylaniline, 164 Methylazoxymethanol, 222, 223 Methylazoxymethanol dehydrogenase, 223 10-Methylbenz[fl]acridine, 436 12-Methylbenz[a]acridine, 436... 

Methylbenz[c]acridine, 436 10-Methylbenz[c]acridine, 436 Methylbenzoquinoline, 429 Methyl-n-butylnitrosamine, 204... 

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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