4-Nitroquinoline oxide

Nitroquinoline 1-oxide [56-57-5] M 190.2, m 157 . Recrystd from aqueous acetone [Seki et al. J Phys Chem 91 126 1987]. 

Stich, H.F. and San, R.H.C., Reduced DNA repair synthesis in Xeroderma pigmentosum cells exposed to the oncogenic 4-nitroquinoline 1-oxide and 4-hydroxayminoquinoline 1-oxide, Mutat. Res., 13,279,1971. 

Nitroquinoline 1-oxide Effect of substitution on /( H, H) in CDC13, including the potentially carcinogenic 2,6- and 2,7-dimethyl derivatives 72JHC1097... 

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. 

Painter, R.B. (1978) Inhibition of DNA replicon initiation by 4-nitroquinoline 1-oxide, adria-mycin, and ethyleneimine. Cancer Res., 38,4445-4449... 

Walker, I.G. (1984) Lack of effect of 4-nitroquinoline 1-oxide on cellular NAD levels. Mutat. Res., 139, 155-159... 

Ito, T., Mitui, H., Udaka, N., Hayashi, H., Okudela, K., Kanisawa, M., and Kitamura, H. 1998. Ki-67 (MIB 5) immunostaining of mouse lung tumors induced by 4-nitroquinoline 1-oxide. Histochem. Cell Biol. 110 589-593. 

AF-2, 2-(2-furyl)-3-(5-nitro-2-furyl)acrylamide AFBj, aflatoxin B1 4NQ0, 4-nitroquinoline 1-oxide B [sJP, benzota]-pyrene DEN, diethylnitrosamine DMN, dimethylnitrosamine. 

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. 

T. Sugimura, K. Okabe, and M. Nagao, The metabolism of 4-nitroquinoline-l-oxide, a carcinogen. 3. An enzyme catalyzing the conversion of 4-nitroquinoline-1-oxide to 4-hydroxyaminoquinoIine-l-oxide in rat liver and hepatomas. Cancer Res. 26 (1966), 1717-1721. 

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 5-chloro-4-nitroquinoline-1-oxide 14076-19-8 25.00 1.5169 2 15924 C9H60S2 di-2-thienylrnethanone 704-38-1 25.00 1.3236 2... 

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... 

C10H8N2O3 5-methyl-4-nitroquinoline-1-oxide 14094-43-0 385.15 32.968 2 18890 C10H9NO N-hydroxy-1 -aminonaphthalene 607-30-7 533.60 47.122 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. 

Dunn, W.J. Ill, and Wold, S. (1978) A structure-cardnogenicity study of 4-nitroquinoline 1-oxides using the SIMCA method of pattern recognition. /. Med. Chem., 21, 1001-1007. 

Nitroquinoline 1-oxide [56-57-5] M 190.2, m 154-155 , 157 . The V-oxide recrystallises from aqueous acetone as yellow needles or platelets. [Ochiai / Org Chem 18 534 1953, Seki et al. / Phys Chem 91 126 1987, Beilstein 20 IIEIV 3396.]... 

Hoshino H, Tanooka H. 1975. Interval effect of -irradiation and subsequent 4-nitroquinoline 1-oxide painting on skin tumor induction in mice. Cancer Res 35 3663-3666. 

Kakunaga, T., "Requirement for Cell Replication In the Fixation and Expression of the Transformed State In Mouse Cells Treated with 4-nItroquInolIne-1-oxIde",... 

Morita, T. Ikeda, S. Minoura, Y. Kojima, M. Tada, M. Polyclonal antibodies to DNA modified with 4 nitroquinoline 1-oxide application for the detection of 4 nitroquinoline 1-oxide-DNA adducts in-vivo. Jpn. J. Cancer Res. (GANN), 79 195-203. 1988. 

In 1992, bacteria were isolated from soils within 30 km of the power plant. Sporeforming bacilli collected nearest to the power plant were more resistant to X-radiation, ultraviolet radiation, and 4-nitroquinoline 1-oxide... 

A soln. of 3-bromo-4-nitroquinoline 1-oxide and 1-morpholinocyclohexene in chloroform stored 10 days at room temp. 6-nitro-l,2,3,4-tetrahydrobenzofuro-[3,2-b]quinoline. Y almost 100%. F. e. s. H. Noda et al., Heterocycles 4, 453 (1976). 

A soln. of 4-nitroquinoline 1-oxide and 2.2 moles 1-morpholinoisobutene in chloroform stored 4 days at room temp. l-hydroxy-2-oxo-3,3-dimethylpyrrolido-[3,2-c]quinoline 5-oxide. Y 49%. T. Yamamori, H. Noda, and M. Hamana, Tetrahedron 31, 945 (1975). 

---