1 2-Nitrofluorene 2- Nitronaphthalene

Iodo-7-nitrofluorene gave 2-iodo-7-aminofluorene in 85% yield by reduction with hydrazine in the presence of Raney nickel [277], and 2-iodo-6-nitronaphthalene and 3-iodo-6-nitronaphthalene afforded the corresponding iodoaminonaphthalenes in almost quantitative yields on treatment with aqueous-alcoholic solutions of sodium hydrosulfite (hyposulfite, dithionite) [257]. 

TABLE 10.20 Direct Mutagenicities in Strain TA98 ( — S9) for 1- and 2-Nitronaphthalene and Several Nitrofluorenes and Nitrodibenzopyranones in the Salmonella typhimurium Plate Incorporation and Microsuspension Preincubation Assays"... 

FIGURE 10.37 Mutagrams of extracts of an ambient sample of gas-phase direct mutagens collected on a PUF plug in Claremont, California, and, for comparison, extracts of the vapor-phase products from the OH radical initiated gas-phase reactions of naphthalene and fluorene in an environmental chamber. For naphthalene, the mutagenicity of fraction 4 is primarily due to the presence of 1- and 2-nitronaphthalene. Fraction 4 from the fluorene reaction contains four nitrofluorene isomers, with 3-nitrofluorene being dominant (adapted from Arey et al., 1992 Harger et al., 1992). 

A comparison of mutagenic activity using normal and nitroreductase-deficient bacteria provides a method for detection and identification of nitroaromatic mutagens. But this idea is complicated by the existence of several bacterial nitroreductases with differing specificities (11). Three different nitroreductase-deficient derivatives of the normal tester strain TA98 were obtained from Dr H. S. Rosenkranz at Case Western University who has isolated and characterized these strains. Strain TA98NR was selected for its resistance to the nitrocompound niridazole and subsequently found to be resistant to the mutagenicity of niridazole, and also to that of the nitrofurans, nitronaphthalenes, and nitrofluorene (3). It is also resistant to 1-nitropyrene and a number of other nitro-PAH... 

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