Nitroquinoline-A-oxide

Among the aromaticSj it was found that 4-nitroquinoline A -oxide [56-57-5] is a powerful carcinogen producing malignant tumors when painted on the skin of mice (80). It was further estabHshed that the 2-methylj 2-ethyl, and 6-chloro derivatives of 4-nitro quinoline oxide are also carcinogens (81). 

Among the numerous quinoline derivatives known to exist, only a few have been tested for carcinogenicity. Positive results have been obtained with quinoline, 4-nitroquinoline A -oxide, and 4-hydroxyaminoquinoline 1-oxide (26). Dong et al. (17) have recently reported that quinoline may also display some activity as a tumor initiator in the two-stage mouse skin carcinogenesis system. Isoquinoline, however, was reportedly inactive under the same test conditions. 

W. Nakahara and F. Fukuoka, Study of carcinogenic mechanism based on experiments with 4-nitroquinoline A -oxide, Gann 50, 1-15 (1959). 

Meihyl-4-nitroquinoline-A/-oxide A/-Melhyl-W-nitrosoaniline W-MeJhyl-W-nitrosourea... 

It would be interesting to know if the mutational consequences of DNA lesions in mammalian cells were the same as those which obtain in bacteria. Methods for retrieving and sequencing mutations in mammalian cells and their viruses are now being developed (81-83) If yeast, a eukaryotic microorganism, can be considered representative of higher eukaryotes, then judging from the observations that the mutational spectra for UV-irradiation and 4-nitroquinoline-l-oxide treatment are identical for yeast (84) and bacteria (85), the spectrum of mutations induced by BPDE in mammalian cells could well resemble those induced in E. coli. 

Diekmann, M., Waldmann, P., Schnurstein, A., Grummt, T, Braunbeck, T. and Nagel, R. (2004) On the relevance of genotoxicity for fish populations 11 genotoxic effects in zebrafish [Danio rerio) exposed to 4-nitroquinoline-l-oxide in a complete life-cycle test. Aquatic Toxicology, 68, 27-37. 

Nishizuka, Y., Nakakuki, K., and Sakakura, T. (1964). Induction of pulmonary tumors and leukemia by a single injection of 4-nitroquinoline 1-oxide to newborn and infant mice, Garm 55,495. 

Sugimura, T., Okabe, K., and Nagao, M. (1966). The metabolism of 4-nitroquinoline-l-oxide, a carcinogen. 3. An enzyme catalyzing the conversion of 4-nitroquinoline-l-oxide to 4-hydroxyaminoquinoline-l-oxide in rat liver and hepatomas. Cancer Res. 26 1717-1721. 

A new approach to the synthesis of 4-alkoxy-l-methyl-2-quinolones has been described (Scheme 3).18 Irradiation of 4-alkoxy-2-methylquinoline 1-oxides (12) (prepared from 2-methyl-4-nitroquinoline 1-oxide) results in photo-rearrangement to give the 2-quinolones (13) as major products a mechanism (Scheme 3) has been proposed. The alkaloids (13 R = Me) and ravenine (13 R = CH2CH=CMe2), which have been synthesized by other means, were prepared in this way. 

Yoshida, K., Tanaka, T., Hirose, Y., Yamaguchi, F., Kohno, H., Toida, M., Hara, A., Sugie, S., Shibata, T. and Mori, H. (2005) Dietary garcinol inhibits 4-nitroquinoline 1-oxide-induced tongue carcinogenesis in rats. Cancer Letters 221 (1), 29-39. 

The reaction of 3-bromo-4-nitroquinoline 1-oxide (220) with 1-morpholinocyclohex-ene 14 gave furoquinoline 228 after treatment with base (equation 48)118. It was demonstrated that the reaction proceeds via a multistep ionic process involving the initial formation of 225 via 221-224 followed by a base-catalyzed enolization to 226 and cyclization to 227 and 228. Apparently, the strong electron-withdrawing effect of the nitro group is essential for the reaction to occur, because similar compounds without the nitro group do not undergo this conversion. 

Tanaka, T, Makita, H., Ohnisih, M., Hirose, Y, Wang, A., Mori, H., Satoh K., Kara, A., and Ogawa, H., Chemoprevention of 4-nitroquinoline 1-oxide-induced oral carcinogenesis by dietary curcumin and hesperidin comparison with the protective effect of P-carotene, Cancer Res., 54, 4653, 1994. 

C9H5CIN203 3>chloro-4 nitroquinoline-1-oxide 14100-52-8 405.90 34.922 2 16003 C9H7F302 a,a,a-trifluoro-p-tolyl)acetic acid 32857-62-8 476.15 41.597 2... 

Dunn III, W.J. and Wold, S. (1978). A Structure-Carcinogenicity Study of 4-Nitroquinoline 1-Oxides Using the SIMCA Method of Pattern Recognition. J.Med.Chem.,21,1001. 

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