Synthesis and characterization of the aqueous solution chemistry of the food-derived carcinogen model N-acetoxy-N-(1-methyl-5H-pyrido[4,5-b]indol-3-yl)acetamide and its N-pivaloyloxy analogue

Tetrahedron

Volumn 59, Issue 40, 2003, Pages 8003-8010

  Rajagopal, Sridharan ^a   Brooks, Michael E ^a   Nguyen, Thach Mien ^a   Novak, Michael ^a  

^a MIAMI UNIVERSITY   (United States)

Author keywords

Food derived carcinogens; Heterocyclic amines; Nitrenium ions

Indexed keywords

1 METHYL 5H PYRIDO[4,5 B]INDOL 3 YLAMMONIUM ACETATE; 3 NITRO 1 METHYL 5H PYRIDO[4,5 B]INDOLE; ACETAMIDE DERIVATIVE; CARCINOGEN; HYDROXAMIC ACID DERIVATIVE; INDOLE DERIVATIVE; N ACETOXY N (1 METHYL 5H PYRIDO[4,5 B]INDOL 3 YL)ACETAMIDE; N HYDROXY N (1 METHYL 5H PYRIDOL[4,5 B]INDOL 3 YL)ACETAMIDE; N PIVALOXY N (1 METHYL 5H PYRIDOL[4,5 B]INDOL 3 YL)ACETAMIDE; UNCLASSIFIED DRUG;

ALKALINITY; AQUEOUS SOLUTION; ARTICLE; CATALYST; COVALENT BOND; DECOMPOSITION; KINETICS; MODEL; OXIDATION; PH MEASUREMENT; PRIORITY JOURNAL; SYNTHESIS;

EID: 0141517554     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.08.005     Document Type: Article

References (38)

1. (a) Felton J.S., Jagerstad M., Knize M.G., Skog K., Wakabayashi K. Nagao M., Sugimura T. Food Borne Carcinogens: Heterocyclic Amines. 2000;31-72 Wiley, New York, (b) Nagao M. Nagao M., Sugimura T. Food Borne Carcinogens: Heterocyclic Amines. 2000;163-196 (c) Yamazoe Y., Nagata K. Nagao M., Sugimura T. Food Borne Carcinogens: Heterocyclic Amines. 2000;74-89 (d) King R.S., Kadlubar F.F., Turesky R.J. Nagao M., Sugimura T. Food Borne Carcinogens: Heterocyclic Amines. 2000;90-111.
2. (a) Felton J.S., Jagerstad M., Knize M.G., Skog K., Wakabayashi K. Nagao M., Sugimura T. Food Borne Carcinogens: Heterocyclic Amines. 2000;31-72 Wiley, New York, (b) Nagao M. Nagao M., Sugimura T. Food Borne Carcinogens: Heterocyclic Amines. 2000;163-196 (c) Yamazoe Y., Nagata K. Nagao M., Sugimura T. Food Borne Carcinogens: Heterocyclic Amines. 2000;74-89 (d) King R.S., Kadlubar F.F., Turesky R.J. Nagao M., Sugimura T. Food Borne Carcinogens: Heterocyclic Amines. 2000;90-111.
3. (a) Felton J.S., Jagerstad M., Knize M.G., Skog K., Wakabayashi K. Nagao M., Sugimura T. Food Borne Carcinogens: Heterocyclic Amines. 2000;31-72 Wiley, New York, (b) Nagao M. Nagao M., Sugimura T. Food Borne Carcinogens: Heterocyclic Amines. 2000;163-196 (c) Yamazoe Y., Nagata K. Nagao M., Sugimura T. Food Borne Carcinogens: Heterocyclic Amines. 2000;74-89 (d) King R.S., Kadlubar F.F., Turesky R.J. Nagao M., Sugimura T. Food Borne Carcinogens: Heterocyclic Amines. 2000;90-111.
4. (a) Felton J.S., Jagerstad M., Knize M.G., Skog K., Wakabayashi K. Nagao M., Sugimura T. Food Borne Carcinogens: Heterocyclic Amines. 2000;31-72 Wiley, New York, (b) Nagao M. Nagao M., Sugimura T. Food Borne Carcinogens: Heterocyclic Amines. 2000;163-196 (c) Yamazoe Y., Nagata K. Nagao M., Sugimura T. Food Borne Carcinogens: Heterocyclic Amines. 2000;74-89 (d) King R.S., Kadlubar F.F., Turesky R.J. Nagao M., Sugimura T. Food Borne Carcinogens: Heterocyclic Amines. 2000;90-111.
5. (a) Hatch F.T., Knize M.G., Felton J.S. Environ. Mol. Mutagen. 17:1991;419 (b) Felton J.S., Knize M.G., Shen N.H., Andersen B.D., Bjeldanes L.F., Hatch F.T. Environ. Health Perspect. 67:1986;17-24 (c) Sugimura T. Environ. Health Perspect. 67:1986;5-10.
6. (a) Hatch F.T., Knize M.G., Felton J.S. Environ. Mol. Mutagen. 17:1991;419 (b) Felton J.S., Knize M.G., Shen N.H., Andersen B.D., Bjeldanes L.F., Hatch F.T. Environ. Health Perspect. 67:1986;17-24 (c) Sugimura T. Environ. Health Perspect. 67:1986;5-10.
7. (a) Hatch F.T., Knize M.G., Felton J.S. Environ. Mol. Mutagen. 17:1991;419 (b) Felton J.S., Knize M.G., Shen N.H., Andersen B.D., Bjeldanes L.F., Hatch F.T. Environ. Health Perspect. 67:1986;17-24 (c) Sugimura T. Environ. Health Perspect. 67:1986;5-10.
8. (a) Sugimura T. Mutat. Res. 150:1985;33-41 (b) Ohgaki H., Matsukura N., Morino K., Kanachi T., Sugimura T., Takayama S. Carcinogenesis. 5:1984;815-819 (c) Eisenbrand O., Tang W. Toxicology. 84:1993;1-82.
9. (a) Sugimura T. Mutat. Res. 150:1985;33-41 (b) Ohgaki H., Matsukura N., Morino K., Kanachi T., Sugimura T., Takayama S. Carcinogenesis. 5:1984;815-819 (c) Eisenbrand O., Tang W. Toxicology. 84:1993;1-82.
10. (a) Sugimura T. Mutat. Res. 150:1985;33-41 (b) Ohgaki H., Matsukura N., Morino K., Kanachi T., Sugimura T., Takayama S. Carcinogenesis. 5:1984;815-819 (c) Eisenbrand O., Tang W. Toxicology. 84:1993;1-82.
11. (a) Yamazoe Y., Shimada M., Kamataki T., Kato R. Cancer Res. 43:1983;5768-5774 (b) Yamazoe Y., Tada M., Kamataki T., Kato R. Biochem. Biophys. Res. Commun. 102:1981;432-439 (c) Gilissen R.A.H., J ., Bamforth K.J., Stavenuiter J.F.C., Coughtrie M.W.H., Meerman J.H.N. Carcinogenesis. 15:1994;39-45 (d) Shinohara A., Saito K., Yamazoe Y., Kamataki T., Kato R. Cancer Res. 46:1986;4362-4367 (e) Yamazoe Y., Shimada M., Kamataki T., Kato R. Biochem. Biophys. Res. Commun. 107:1982;165-172 (f) Snyderwine E.G., Wirth P.J., Roller P.P., Adamson R.H., Sato S., Thorgeirsson S.S. Carcinogenesis. 9:1988;411-418 (g) Meerman J.H.N., Ringer D.P., Coughtrie M.W.H., Bamforth K.J., Gilissen R.A.H.J. Chem.-Biol. Interact. 92:1994;321-328.
12. (a) Yamazoe Y., Shimada M., Kamataki T., Kato R. Cancer Res. 43:1983;5768-5774 (b) Yamazoe Y., Tada M., Kamataki T., Kato R. Biochem. Biophys. Res. Commun. 102:1981;432-439 (c) Gilissen R.A.H., J ., Bamforth K.J., Stavenuiter J.F.C., Coughtrie M.W.H., Meerman J.H.N. Carcinogenesis. 15:1994;39-45 (d) Shinohara A., Saito K., Yamazoe Y., Kamataki T., Kato R. Cancer Res. 46:1986;4362-4367 (e) Yamazoe Y., Shimada M., Kamataki T., Kato R. Biochem. Biophys. Res. Commun. 107:1982;165-172 (f) Snyderwine E.G., Wirth P.J., Roller P.P., Adamson R.H., Sato S., Thorgeirsson S.S. Carcinogenesis. 9:1988;411-418 (g) Meerman J.H.N., Ringer D.P., Coughtrie M.W.H., Bamforth K.J., Gilissen R.A.H.J. Chem.-Biol. Interact. 92:1994;321-328.
13. (a) Yamazoe Y., Shimada M., Kamataki T., Kato R. Cancer Res. 43:1983;5768-5774 (b) Yamazoe Y., Tada M., Kamataki T., Kato R. Biochem. Biophys. Res. Commun. 102:1981;432-439 (c) Gilissen R.A.H., J ., Bamforth K.J., Stavenuiter J.F.C., Coughtrie M.W.H., Meerman J.H.N. Carcinogenesis. 15:1994;39-45 (d) Shinohara A., Saito K., Yamazoe Y., Kamataki T., Kato R. Cancer Res. 46:1986;4362-4367 (e) Yamazoe Y., Shimada M., Kamataki T., Kato R. Biochem. Biophys. Res. Commun. 107:1982;165-172 (f) Snyderwine E.G., Wirth P.J., Roller P.P., Adamson R.H., Sato S., Thorgeirsson S.S. Carcinogenesis. 9:1988;411-418 (g) Meerman J.H.N., Ringer D.P., Coughtrie M.W.H., Bamforth K.J., Gilissen R.A.H.J. Chem.-Biol. Interact. 92:1994;321-328.
14. (a) Yamazoe Y., Shimada M., Kamataki T., Kato R. Cancer Res. 43:1983;5768-5774 (b) Yamazoe Y., Tada M., Kamataki T., Kato R. Biochem. Biophys. Res. Commun. 102:1981;432-439 (c) Gilissen R.A.H., J ., Bamforth K.J., Stavenuiter J.F.C., Coughtrie M.W.H., Meerman J.H.N. Carcinogenesis. 15:1994;39-45 (d) Shinohara A., Saito K., Yamazoe Y., Kamataki T., Kato R. Cancer Res. 46:1986;4362-4367 (e) Yamazoe Y., Shimada M., Kamataki T., Kato R. Biochem. Biophys. Res. Commun. 107:1982;165-172 (f) Snyderwine E.G., Wirth P.J., Roller P.P., Adamson R.H., Sato S., Thorgeirsson S.S. Carcinogenesis. 9:1988;411-418 (g) Meerman J.H.N., Ringer D.P., Coughtrie M.W.H., Bamforth K.J., Gilissen R.A.H.J. Chem.-Biol. Interact. 92:1994;321-328.
15. (a) Yamazoe Y., Shimada M., Kamataki T., Kato R. Cancer Res. 43:1983;5768-5774 (b) Yamazoe Y., Tada M., Kamataki T., Kato R. Biochem. Biophys. Res. Commun. 102:1981;432-439 (c) Gilissen R.A.H., J ., Bamforth K.J., Stavenuiter J.F.C., Coughtrie M.W.H., Meerman J.H.N. Carcinogenesis. 15:1994;39-45 (d) Shinohara A., Saito K., Yamazoe Y., Kamataki T., Kato R. Cancer Res. 46:1986;4362-4367 (e) Yamazoe Y., Shimada M., Kamataki T., Kato R. Biochem. Biophys. Res. Commun. 107:1982;165-172 (f) Snyderwine E.G., Wirth P.J., Roller P.P., Adamson R.H., Sato S., Thorgeirsson S.S. Carcinogenesis. 9:1988;411-418 (g) Meerman J.H.N., Ringer D.P., Coughtrie M.W.H., Bamforth K.J., Gilissen R.A.H.J. Chem.-Biol. Interact. 92:1994;321-328.
16. (a) Yamazoe Y., Shimada M., Kamataki T., Kato R. Cancer Res. 43:1983;5768-5774 (b) Yamazoe Y., Tada M., Kamataki T., Kato R. Biochem. Biophys. Res. Commun. 102:1981;432-439 (c) Gilissen R.A.H., J ., Bamforth K.J., Stavenuiter J.F.C., Coughtrie M.W.H., Meerman J.H.N. Carcinogenesis. 15:1994;39-45 (d) Shinohara A., Saito K., Yamazoe Y., Kamataki T., Kato R. Cancer Res. 46:1986;4362-4367 (e) Yamazoe Y., Shimada M., Kamataki T., Kato R. Biochem. Biophys. Res. Commun. 107:1982;165-172 (f) Snyderwine E.G., Wirth P.J., Roller P.P., Adamson R.H., Sato S., Thorgeirsson S.S. Carcinogenesis. 9:1988;411-418 (g) Meerman J.H.N., Ringer D.P., Coughtrie M.W.H., Bamforth K.J., Gilissen R.A.H.J. Chem.-Biol. Interact. 92:1994;321-328.
17. (a) Yamazoe Y., Shimada M., Kamataki T., Kato R. Cancer Res. 43:1983;5768-5774 (b) Yamazoe Y., Tada M., Kamataki T., Kato R. Biochem. Biophys. Res. Commun. 102:1981;432-439 (c) Gilissen R.A.H., J ., Bamforth K.J., Stavenuiter J.F.C., Coughtrie M.W.H., Meerman J.H.N. Carcinogenesis. 15:1994;39-45 (d) Shinohara A., Saito K., Yamazoe Y., Kamataki T., Kato R. Cancer Res. 46:1986;4362-4367 (e) Yamazoe Y., Shimada M., Kamataki T., Kato R. Biochem. Biophys. Res. Commun. 107:1982;165-172 (f) Snyderwine E.G., Wirth P.J., Roller P.P., Adamson R.H., Sato S., Thorgeirsson S.S. Carcinogenesis. 9:1988;411-418 (g) Meerman J.H.N., Ringer D.P., Coughtrie M.W.H., Bamforth K.J., Gilissen R.A.H.J. Chem.-Biol. Interact. 92:1994;321-328.
18. (a) Novak M., Xu L., Wolf R.A. J. Am. Chem. Soc. 120:1998;1643-1644 (b) Novak M., Kazerani S. J. Am. Chem. Soc. 122:2000;3606-3616 (c) Novak M., Toth K., Rajagopal S., Brooks M.E., Hott L.L., Moslener M. J. Am. Chem. Soc. 124:2002;7972-7981 (d) Novak M., Nguyen T.-M. J. Org. Chem. 2003;. in press (e) Novak M., Rajagopal S. Richard J.P., Tidwell T.T. Advances in Physical Organic Chemistry. Vol. 36:2001;167-254 Academic, New York.
19. (a) Novak M., Xu L., Wolf R.A. J. Am. Chem. Soc. 120:1998;1643-1644 (b) Novak M., Kazerani S. J. Am. Chem. Soc. 122:2000;3606-3616 (c) Novak M., Toth K., Rajagopal S., Brooks M.E., Hott L.L., Moslener M. J. Am. Chem. Soc. 124:2002;7972-7981 (d) Novak M., Nguyen T.-M. J. Org. Chem. 2003;. in press (e) Novak M., Rajagopal S. Richard J.P., Tidwell T.T. Advances in Physical Organic Chemistry. Vol. 36:2001;167-254 Academic, New York.
20. (a) Novak M., Xu L., Wolf R.A. J. Am. Chem. Soc. 120:1998;1643-1644 (b) Novak M., Kazerani S. J. Am. Chem. Soc. 122:2000;3606-3616 (c) Novak M., Toth K., Rajagopal S., Brooks M.E., Hott L.L., Moslener M. J. Am. Chem. Soc. 124:2002;7972-7981 (d) Novak M., Nguyen T.-M. J. Org. Chem. 2003;. in press (e) Novak M., Rajagopal S. Richard J.P., Tidwell T.T. Advances in Physical Organic Chemistry. Vol. 36:2001;167-254 Academic, New York.
21. (a) Novak M., Xu L., Wolf R.A. J. Am. Chem. Soc. 120:1998;1643-1644 (b) Novak M., Kazerani S. J. Am. Chem. Soc. 122:2000;3606-3616 (c) Novak M., Toth K., Rajagopal S., Brooks M.E., Hott L.L., Moslener M. J. Am. Chem. Soc. 124:2002;7972-7981 (d) Novak M., Nguyen T.-M. J. Org. Chem. 2003;. in press (e) Novak M., Rajagopal S. Richard J.P., Tidwell T.T. Advances in Physical Organic Chemistry. Vol. 36:2001;167-254 Academic, New York.
22. (a) Novak M., Xu L., Wolf R.A. J. Am. Chem. Soc. 120:1998;1643-1644 (b) Novak M., Kazerani S. J. Am. Chem. Soc. 122:2000;3606-3616 (c) Novak M., Toth K., Rajagopal S., Brooks M.E., Hott L.L., Moslener M. J. Am. Chem. Soc. 124:2002;7972-7981 (d) Novak M., Nguyen T.-M. J. Org. Chem. 2003;. in press (e) Novak M., Rajagopal S. Richard J.P., Tidwell T.T. Advances in Physical Organic Chemistry. Vol. 36:2001;167-254 Academic, New York.
23. (a) Molina P., Almendros P., Fresneda P.M. Tetrahedron Lett. 34:1993;4701-4704 (b) Akimoto H., Kawai A., Nomura H., Nagao M., Kawachi T., Sugimura T. Chem. Lett. 1977;1061-1064 (c) Hibino S., Sugino E., Kuwada T., Ogura N., Sato K., Choshi T. J. Org. Chem. 57:1992;5917-5921.
24. (a) Molina P., Almendros P., Fresneda P.M. Tetrahedron Lett. 34:1993;4701-4704 (b) Akimoto H., Kawai A., Nomura H., Nagao M., Kawachi T., Sugimura T. Chem. Lett. 1977;1061-1064 (c) Hibino S., Sugino E., Kuwada T., Ogura N., Sato K., Choshi T. J. Org. Chem. 57:1992;5917-5921.
25. (a) Molina P., Almendros P., Fresneda P.M. Tetrahedron Lett. 34:1993;4701-4704 (b) Akimoto H., Kawai A., Nomura H., Nagao M., Kawachi T., Sugimura T. Chem. Lett. 1977;1061-1064 (c) Hibino S., Sugino E., Kuwada T., Ogura N., Sato K., Choshi T. J. Org. Chem. 57:1992;5917-5921.
26. Takeda K., Ohta T., Shudo K., Okamoto T., Tsuji K., Kosuge T. Chem. Pharm. Bull. 25:1977;2145-2146.
27. Schindler W. Helv. Chim. Acta. 40:1957;2156-2159.
28. (a) Saito K., Yamazoe Y., Kamataki T., Kato R. Carcinogenesis. 4:1983;1547-1550 (b) Hashimoto Y., Shudo K., Okamoto T. Biochem. Biophy. Res. Commun. 96:1980;355-362.
29. (a) Saito K., Yamazoe Y., Kamataki T., Kato R. Carcinogenesis. 4:1983;1547-1550 (b) Hashimoto Y., Shudo K., Okamoto T. Biochem. Biophy. Res. Commun. 96:1980;355-362.
30. (a) Hashimoto Y., Shudo K., Okamoto T. J. Am. Chem. Soc. 104:1982;7636-7640 Toth, K. PhD Thesis, Miami University, 2001.
31. (a) Hashimoto Y., Shudo K., Okamoto T. J. Am. Chem. Soc. 104:1982;7636-7640 Toth, K. PhD Thesis, Miami University, 2001.
32. Novak M., Kazerani S. J. Org. Chem. 63:1998;895-897.
33. Famulok M., Bosold F., Boche G. Tetrahedron Lett. 30:1989;321-324.
34. -]≤10 mM.
35. Novak M., Rajagopal S. Chem. Res. Toxicol. 15:2002;1495-1503.
36. Sugimura T. Mutat. Res. 150:1985;33-41.
37. (a) Taft R.W. J. Am. Chem. Soc. 74:1952;2729-2732 (b) Revis C.L., Rajamaki M., Fishbein J.C. J. Org. Chem. 7733:1995;77381.
38. (a) Taft R.W. J. Am. Chem. Soc. 74:1952;2729-2732 (b) Revis C.L., Rajamaki M., Fishbein J.C. J. Org. Chem. 7733:1995;77381.