Aminofluoren

Hydrazine hydrate, in preparation of sulfonylhydrazides, 40, 93, OS in reduction of 2-nitrofiuorene to 2-aminofluorene, 40, 5 in Wolff-Kishner reduction, 43, 34 Hydrazines, asymmetrically substituted by N-aminatiou of amines by hydroxylamine-O-sulfonic acid, 43,2... 

Phenobarbital, trans stilbene oxide, 2-acetyl aminofluorene Various, including phenobarbital... 

Very interesting information relevant to the stereochemical results of alkylation of DNA comes from studies of nucleosides alkylated by activated PAHs. Eight such structures have been reported (115-118). Three are products of the interaction of chloromethyl PAHs with N6 of adenosine XXX-XXXII, two with deoxyadenosine (XXXIII, XXXIV), two are para-substituted benzyl derivatives of guanosine, alkylated at 0-6 (XXXV, XXXVI) (117) and one is an acetyl aminofluorene derivative of guanosine, alkylated at C8 (XXXVII) (118). 

The metabolic formation of N-sulfonyloxy-N-acetyl-2-aminofluorene (N-sulfonyloxy-AAF) and its observed electrophilic reactivity, provided the first evidence for the importance of enzymatic conjugation reactions in chemical carcinogenesis (23,24). This reaction was shown to be catalyzed by PAPS-dependent sulfotrans-ferases that are located predominantly in liver cytosol and has been subsequently demonstrated for N-hydroxy arylamide metabolites of several other carcinogens, including N-acetyl-4-aminobiphenyl (AABP), benzidine, N-acetyl-2-aminophenanthrene and phenacetin. 

Certain nitro PAHs appear to require metabolism of their N-hydroxy arylamine derivatives in order to induce mutations. For example, while 2-nitrofluorene showed decreased mutagenicity in the nitroreductase-deficient mutant, TA98NR, and in strain TA98/1,8-DNP, its presumed ultimate mutagenic derivative, N-hydroxy-2-aminofluorene was inactive in only strain TA98/1,8-DNP (117). Observations such as these led McCoy t al. (117) to... 

Attempts to utilize an in situ diazotization procedure (1.2 equiv. isoamyl nitrite, acetic acid, 25 °C, 30 min) [58,60-62] for DNA cleavage were made via generation of diazonium compound 17 directly from commercially available 9-aminofluorene (Fig. 18) [58]. However, addition of this solution to aqueous buffers (pH = 4-7) did not produce any DNA cleavage neither did the addition of cuprous chloride, which had been demonstrated to be successful in activating diazonium compounds for DNA cleavage [60-62]. This may be explained by ... 

A closer look at Figs. 18 and 19 helps explain the lack of DNA cleavage obtained on diazotization of 9-aminofluorene and its potential in DNA cleavage. The diazonium salt 17 (once formed) may either ... 

The isolation of diazobenzo[fr ]fluorenes as stable antitumor natural products raises several questions about their mode of action. The inability to cleave DNA by diazotization of 9-aminofluorene may imply that if the diazo functionality is involved in the mode of interaction of kinamycins with DNA, its conversion to diazonium and the ensuing reduction may seem to be of negligible importance. An additional possibility, which will be discussed later, is that 9-diazofluorene may not be the ideal model for these natural products. In exploring DNA cleavage as a possible route to the kinamycins role as a stable antitumor agent, which may supplement their speculative and as yet unconfirmed role as alkylating molecules [67], this early model seemed to suggest that the well-established activation of diazonium may not be relevant. 

Lai CC, Miller JA, Miller EC, et al. N-sulfooxy-2-aminofluorene is the major ultimate electrophilic and carcinogenic metabolite of N-hydroxy-2-acetylaminofluorene in the livers of infant male C57BL/6J x C3H/HeJ FI (B6C3F1) mice. Carcinogenesis 1985 6(7) 1037— 1045. 

Several 2-amino-2-deoxy-D-gulononitrile derivatives (68) have been obtained by treating D-xylose with hydrogen cyanide and an amine. Among the amines that were used in preparing these derivatives were aniline,107-109 9-aminofluorene,110 p-methylphenylamine,109 and benzylamine.109 In all cases, as expected, both the D- and L-gly-cero configurations at C-2 are formed. When a solution of 68 (R = Ph)... 

Benzo[a]pyrene and other polycyclic aromatic hydrocarbons CYP1A2 Acetaminophen 2-Acetylaminofluorene 4-Aminobiphenyl 2-Aminofluorene 2-Naphthylamine NNK ... 

C. C. Lai, E. C. Miller, A. Liem, The Essential Role of Microsomal Deacetylase Activity in the Metabolic Activation, DNA-(Deoxyguanosin-8-yl)-2-aminofluorene Adduct Formation and Initiation of Liver Tumors by A-Hydroxy-2-acetylaminofluorene in the Livers of Infant Male B6C3Fj Mice , Carcinogenesis 1988, 9, 1295-1302. 

Synonyms AAF 2-AAF 2-Acetamidofluorene 2-Acetaminofluorene 2-Acetoaminofluorene 2-(Acetylamino)fluorene A-Acetyl-2-aminofluorene 2-Aminoacetylfluorene AI3-52433 BRN 2807677 CCRIS 1 EINECS 200-188-6 FAA 2-FAA 2-Fluorenilacetamide A-9 -Fluoren-2-ylacetamide 2-Fluorenylacetamide 7V-2-Fluorenylacetamide A-Fluoren-2-acetylacetamide N-Fluorenyl-2-acetamlde NSC 12279 RCRA waste number U005 UN 3143. 

Acetoxypropane, see Isopropyl acetate Acetyl acetate, see Acetic anhydride Acetyl aldehyde, see Acetaldehyde 2-(Acetylamino)fluorene, see 2-Acetylaminofluorene A-Acetyl-2-aminofluorene, see 2-Acetylaminofluorene Acetyl anhydride, see Acetic anhydride... 

Figure 1. The "spot test. Each petri plate contains, in a thin overlay of top agar, the tester strain TA98 and, in the cases of plates C and D, a liver microsomal activation system (S-9 Mix). Mutagens were applied to 6-mm filter-paper discs which were then placed in the center of each plate (A) spontaneous revertants (B) furyl-furamide (AF-2) (1 fig) (C) aflotoxin Bi(l fig) (D) 2-aminofluorene (10 fig). Mutagen-induced revertants appear as a ring of colonies around each disc (3).

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