Fluorinated benzo[h]quinolines and benzo[f]quinolines

Chemical and Pharmaceutical Bulletin

Volumn 44, Issue 12, 1996, Pages 2254-2258

  Saeki, Ken Ichi ^a   Tomomitsu, Masato ^a   Kawazoe, Yutaka ^a   Momota, Kunitaka ^b   Kimoto, Hiroshi ^c  

^a NAGOYA CITY UNIVERSITY   (Japan)

^b Morita Chemical Industries Co Ltd   (Japan)

^c NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

benzoquinolines; electrochemical fluorination; fluorine substitution

Indexed keywords

BENZO[A]QUINOLIZINE DERIVATIVE;

ARTICLE; DRUG EFFECT; ELECTROLYSIS; FLUORINATION; GENOTOXICITY; MOLECULAR INTERACTION; MUTAGENESIS;

EID: 0030466494     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.44.2254     Document Type: Article

References (30)

1. Jerina D. M., Yagi H., Lehr R. E., Thakker D. R., Schaefer-Ridder M., Karle J. M., Levin W., Wood A. W., Chang R. L., Conney A. H., "Polycyclic Hydrocarbons Cancer," Vol. 1, ed. by Gelboin H. V., Ts'o Paul O. P., Academic Press, New York, 1978, pp. 173-188.
2. McCann J., Choi E., Yamazaki E., Ames B. N., Proc. Natl. Acad. Sci. U.S.A., 72, 5135-5139 (1975); Hirano K., Shinohara Y., Tsuda H., Fukushima S., Takahashi M., Ito N., Cancer Res., 36, 329-335 (1976).
3. McCann J., Choi E., Yamazaki E., Ames B. N., Proc. Natl. Acad. Sci. U.S.A., 72, 5135-5139 (1975); Hirano K., Shinohara Y., Tsuda H., Fukushima S., Takahashi M., Ito N., Cancer Res., 36, 329-335 (1976).
4. Tada M., Takahashi K., Kawazoe Y., Chem. Pharm. Bull., 30, 3834-3837 (1982); idem, Chem.-Biol. Interactions, 29, 257-266 (1980); Saeki K., Takahashi K., Kawazoe Y., Biol. Pharm. Bull., 19, 541-546 (1996).
5. Tada M., Takahashi K., Kawazoe Y., Chem. Pharm. Bull., 30, 3834-3837 (1982); idem, Chem.-Biol. Interactions, 29, 257-266 (1980); Saeki K., Takahashi K., Kawazoe Y., Biol. Pharm. Bull., 19, 541-546 (1996).
6. Tada M., Takahashi K., Kawazoe Y., Chem. Pharm. Bull., 30, 3834-3837 (1982); idem, Chem.-Biol. Interactions, 29, 257-266 (1980); Saeki K., Takahashi K., Kawazoe Y., Biol. Pharm. Bull., 19, 541-546 (1996).
7. Takahashi K., Kamiya M., Sengoku Y., Kohda K., Kawazoe Y., Chem. Pharm. Bull., 36, 4630-4633 (1988); Kamiya M., Sengoku Y., Takahashi K., Kohda K., Kawazoe Y., "Antimutagenesis and Anticarcinogenesis," II, ed. by Kuroda Y., Shankel D. M., Waters M. D., Plenum Publishing Corp., New York, 1990, pp. 441-446; Saeki K., Takahashi K., Kawazoe Y., Biol. Pharm. Bull., 16, 232-234 (1993).
8. Takahashi K., Kamiya M., Sengoku Y., Kohda K., Kawazoe Y., Chem. Pharm. Bull., 36, 4630-4633 (1988); Kamiya M., Sengoku Y., Takahashi K., Kohda K., Kawazoe Y., "Antimutagenesis and Anticarcinogenesis," II, ed. by Kuroda Y., Shankel D. M., Waters M. D., Plenum Publishing Corp., New York, 1990, pp. 441-446; Saeki K., Takahashi K., Kawazoe Y., Biol. Pharm. Bull., 16, 232-234 (1993).
9. Takahashi K., Kamiya M., Sengoku Y., Kohda K., Kawazoe Y., Chem. Pharm. Bull., 36, 4630-4633 (1988); Kamiya M., Sengoku Y., Takahashi K., Kohda K., Kawazoe Y., "Antimutagenesis and Anticarcinogenesis," II, ed. by Kuroda Y., Shankel D. M., Waters M. D., Plenum Publishing Corp., New York, 1990, pp. 441-446; Saeki K., Takahashi K., Kawazoe Y., Biol. Pharm. Bull., 16, 232-234 (1993).
10. LaVoie E. J., Tulley-Freiler L., Bedenke V., Hoffmann D., Mutation Res., 116, 91-102 (1983); Hecht S. S., LaVoie E. J., Bedenko V., Pingaro L., Katayama S., Hoffmann D., Sardella D. J., Boger E., Lehr R. E., Cancer Res., 41, 4341-4345 (1981); Hubenman E., Slaga T. J., ibid., 39, 411-414 (1979); Diamond L., Cherian K., Harvey R. G., DiGiovanni J., Mutation Res., 136, 65-72 (1984); Miller E. C., Miller J. A., Cancer Res., 20, 133-137 (1960); Miller J. A., Miller E. C., Finger G. C., ibid., 13, 93-97 (1953); idem., ibid., 17, 387-398 (1957).
11. LaVoie E. J., Tulley-Freiler L., Bedenke V., Hoffmann D., Mutation Res., 116, 91-102 (1983); Hecht S. S., LaVoie E. J., Bedenko V., Pingaro L., Katayama S., Hoffmann D., Sardella D. J., Boger E., Lehr R. E., Cancer Res., 41, 4341-4345 (1981); Hubenman E., Slaga T. J., ibid., 39, 411-414 (1979); Diamond L., Cherian K., Harvey R. G., DiGiovanni J., Mutation Res., 136, 65-72 (1984); Miller E. C., Miller J. A., Cancer Res., 20, 133-137 (1960); Miller J. A., Miller E. C., Finger G. C., ibid., 13, 93-97 (1953); idem., ibid., 17, 387-398 (1957).
12. LaVoie E. J., Tulley-Freiler L., Bedenke V., Hoffmann D., Mutation Res., 116, 91-102 (1983); Hecht S. S., LaVoie E. J., Bedenko V., Pingaro L., Katayama S., Hoffmann D., Sardella D. J., Boger E., Lehr R. E., Cancer Res., 41, 4341-4345 (1981); Hubenman E., Slaga T. J., ibid., 39, 411-414 (1979); Diamond L., Cherian K., Harvey R. G., DiGiovanni J., Mutation Res., 136, 65-72 (1984); Miller E. C., Miller J. A., Cancer Res., 20, 133-137 (1960); Miller J. A., Miller E. C., Finger G. C., ibid., 13, 93-97 (1953); idem., ibid., 17, 387-398 (1957).
13. LaVoie E. J., Tulley-Freiler L., Bedenke V., Hoffmann D., Mutation Res., 116, 91-102 (1983); Hecht S. S., LaVoie E. J., Bedenko V., Pingaro L., Katayama S., Hoffmann D., Sardella D. J., Boger E., Lehr R. E., Cancer Res., 41, 4341-4345 (1981); Hubenman E., Slaga T. J., ibid., 39, 411-414 (1979); Diamond L., Cherian K., Harvey R. G., DiGiovanni J., Mutation Res., 136, 65-72 (1984); Miller E. C., Miller J. A., Cancer Res., 20, 133-137 (1960); Miller J. A., Miller E. C., Finger G. C., ibid., 13, 93-97 (1953); idem., ibid., 17, 387-398 (1957).
14. LaVoie E. J., Tulley-Freiler L., Bedenke V., Hoffmann D., Mutation Res., 116, 91-102 (1983); Hecht S. S., LaVoie E. J., Bedenko V., Pingaro L., Katayama S., Hoffmann D., Sardella D. J., Boger E., Lehr R. E., Cancer Res., 41, 4341-4345 (1981); Hubenman E., Slaga T. J., ibid., 39, 411-414 (1979); Diamond L., Cherian K., Harvey R. G., DiGiovanni J., Mutation Res., 136, 65-72 (1984); Miller E. C., Miller J. A., Cancer Res., 20, 133-137 (1960); Miller J. A., Miller E. C., Finger G. C., ibid., 13, 93-97 (1953); idem., ibid., 17, 387-398 (1957).
15. LaVoie E. J., Tulley-Freiler L., Bedenke V., Hoffmann D., Mutation Res., 116, 91-102 (1983); Hecht S. S., LaVoie E. J., Bedenko V., Pingaro L., Katayama S., Hoffmann D., Sardella D. J., Boger E., Lehr R. E., Cancer Res., 41, 4341-4345 (1981); Hubenman E., Slaga T. J., ibid., 39, 411-414 (1979); Diamond L., Cherian K., Harvey R. G., DiGiovanni J., Mutation Res., 136, 65-72 (1984); Miller E. C., Miller J. A., Cancer Res., 20, 133-137 (1960); Miller J. A., Miller E. C., Finger G. C., ibid., 13, 93-97 (1953); idem., ibid., 17, 387-398 (1957).
16. LaVoie E. J., Tulley-Freiler L., Bedenke V., Hoffmann D., Mutation Res., 116, 91-102 (1983); Hecht S. S., LaVoie E. J., Bedenko V., Pingaro L., Katayama S., Hoffmann D., Sardella D. J., Boger E., Lehr R. E., Cancer Res., 41, 4341-4345 (1981); Hubenman E., Slaga T. J., ibid., 39, 411-414 (1979); Diamond L., Cherian K., Harvey R. G., DiGiovanni J., Mutation Res., 136, 65-72 (1984); Miller E. C., Miller J. A., Cancer Res., 20, 133-137 (1960); Miller J. A., Miller E. C., Finger G. C., ibid., 13, 93-97 (1953); idem., ibid., 17, 387-398 (1957).
17. For example; Welch J. T., Tetrahedron, 43, 3123-3197 (1987).
18. Takeuchi I., Hamada Y., Hirota M., Chem. Pharm. Bull., 41, 747-751 (1993).
19. Momota K., Morita M., Matsuda Y., Electrochimica Acta, 38, 619-624 (1993); idem, ibid., 38, 1123-1130 (1993); Momota K., Kato K., Morita M., Matsuda Y., ibid, 39, 41-47 (1994); Morita K., Kato K., Morita M., Matsuda Y., ibid., 39, 681-690 (1994); Momota K., Horio H., Kato K., Morita M., Matsuda Y., ibid., 40, 233-240 (1995); and references cited therein.
20. Momota K., Morita M., Matsuda Y., Electrochimica Acta, 38, 619-624 (1993); idem, ibid., 38, 1123-1130 (1993); Momota K., Kato K., Morita M., Matsuda Y., ibid, 39, 41-47 (1994); Morita K., Kato K., Morita M., Matsuda Y., ibid., 39, 681-690 (1994); Momota K., Horio H., Kato K., Morita M., Matsuda Y., ibid., 40, 233-240 (1995); and references cited therein.
21. Momota K., Morita M., Matsuda Y., Electrochimica Acta, 38, 619-624 (1993); idem, ibid., 38, 1123-1130 (1993); Momota K., Kato K., Morita M., Matsuda Y., ibid, 39, 41-47 (1994); Morita K., Kato K., Morita M., Matsuda Y., ibid., 39, 681-690 (1994); Momota K., Horio H., Kato K., Morita M., Matsuda Y., ibid., 40, 233-240 (1995); and references cited therein.
22. Momota K., Morita M., Matsuda Y., Electrochimica Acta, 38, 619-624 (1993); idem, ibid., 38, 1123-1130 (1993); Momota K., Kato K., Morita M., Matsuda Y., ibid, 39, 41-47 (1994); Morita K., Kato K., Morita M., Matsuda Y., ibid., 39, 681-690 (1994); Momota K., Horio H., Kato K., Morita M., Matsuda Y., ibid., 40, 233-240 (1995); and references cited therein.
23. Momota K., Morita M., Matsuda Y., Electrochimica Acta, 38, 619-624 (1993); idem, ibid., 38, 1123-1130 (1993); Momota K., Kato K., Morita M., Matsuda Y., ibid, 39, 41-47 (1994); Morita K., Kato K., Morita M., Matsuda Y., ibid., 39, 681-690 (1994); Momota K., Horio H., Kato K., Morita M., Matsuda Y., ibid., 40, 233-240 (1995); and references cited therein.
24. Momota K., Yonezawa T., Hayakawa Y., Kato K., Morita M., Matsuda Y., J. Applied Electrochem., 25, 651-658 (1995).
25. Wei W., Saeki K., Kawazoe Y., Heterocycles, 41, 315-322 (1995).
26. Saeki K., Kohda K., Kawazoe Y., Sakamoto Y., Heterocycles, 33, 35-38 (1992).
27. Iwai K., Hara S., Yakugaku Zasshi, 70, 394-400 (1950); Iwai K., Hara S., Saeki S., ibid., 71, 1152-1158 (1951); Ochiai E., Tamura S., ibid., 72, 985-988 (1952).
28. Iwai K., Hara S., Yakugaku Zasshi, 70, 394-400 (1950); Iwai K., Hara S., Saeki S., ibid., 71, 1152-1158 (1951); Ochiai E., Tamura S., ibid., 72, 985-988 (1952).
29. Iwai K., Hara S., Yakugaku Zasshi, 70, 394-400 (1950); Iwai K., Hara S., Saeki S., ibid., 71, 1152-1158 (1951); Ochiai E., Tamura S., ibid., 72, 985-988 (1952).
30. Adcock W., Dewar J. S., J. Am. Chem. Soc., 89, 386-390 (1967).