Synthesis of 1H-2,3-dihydropyrrolizine derivatives as precursors of bifunctional alkylating agents

Tetrahedron

Volumn 58, Issue 52, 2002, Pages 10407-10412

  Rajaraman, Shanthi ^a   Jimenez, Leslie S ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

Antitumor agents; Bifunctional alkylating agents; Dihydropyrrolizine

Indexed keywords

ALKYLATING AGENT; DANAIDONE; KETONE DERIVATIVE; PHEROMONE; POTASSIUM NITRATE; PYRROLIZINE DERIVATIVE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRON; HYDROGENATION; NITRATION; OXIDATION; PRIORITY JOURNAL;

EID: 0037164635     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01419-9     Document Type: Article

References (35)

1. (a) Iver V.N., Szybalski W. Science. 145:1964;55-58
2. (b) Tomasz M., Lipman R., Chowdary D., Pawlik J., Verdine G., Nakanishi K. Science. 235:1987;1204-1208
3. (c) Cera C., Egbertson M., Teng S., Crothers D., Danishefsky S. Biochemistry. 28:1989;5665-5669
4. (d) Li V.-S., Tang M.-, Kohn H. J. Am. Chem. Soc. 114:1992;5501-5509
5. (e) Woo J., Sigurdsson S.T., Hopkins P.B. J. Am. Chem. Soc. 115:1993;1199-1200
6. (f) Woo J., Sigurdsson S.T., Hopkins P.B. J. Am. Chem. Soc. 115:1993;3407-3415
7. (g) Paz M.M., Hopkins P.B. J. Am. Chem. Soc. 119:1997;5999-6005
8. (h) Williams R.M., Rajski S.R., Rollins S.B. Chem. Biol. 4:1997;127-137.
9. (i) For a good review of DNA cross-linking agents, see: Rajski S.R., Williams R.M. Chem. Rev. 98:1998;2723-2795.
10. Niwa H., Ogawa T., Okamoto O., Yamada K. Tetrahedron Lett. 32:1991;927-930.
11. Weidner M.F., Sigurdsson S.T., Hopkins P.B. Biochemistry. 29:1990;9225-9233.
12. Teng S., Woodson S., Crothers D. Biochemistry. 28:1989;3901-3907.
13. Bergeron M., Evans S.M., Sharp F.R., Koch C.J., Lord E.M., Ferriero D.M. Neuroscience. 89:1999;1357-1366.
14. (a) Siim B.G., Denny W.A., Wilson W.R. Oncol. Res. 9:1997;257-369
15. (b) Wilson W.R., Ferry D.M., Tercel M., Anderson R.F., Denny W.A. Radiat. Res. 149:1998;237-245
16. (c) Berry J.M., Watson C.Y., Whish W.J.D., Threadgill M.D. J. Chem. Soc., Perkin Trans. 1. 1997;1147-1156
17. (d) Hay M.P., Wilson W.R., Denny W.A. Tetrahedron. 56:2000;645-657
18. (e) Lee A.E., Wilson W.R. Toxicol. Appl. Pharmacol. 163:2000;50-59
19. (f) Kestell P., Pruijn F.B., Siim B.G., Palmer B.D., Wilson W.R. Cancer Chemother. Pharmacol. 46:2000;365-374.
20. Mattocks A.R. Chemistry and Toxicology of Pyrrolizine Alkaloids. 1986;Academic, Orlando.
21. (a) Meinwald J., Meinwald Y. J. Am. Chem. Soc. 88:1966;1305-1310
22. (b) Roeder E., Wiedenfeld H., Bourauel T. Liebigs Ann. Chem. 1985;1708-1710.
23. (a) Winterfeldt E. Synthesis. 1975;617-630
24. (b) Ruggeri R.B., Hansen M.M., Heathcock C.H. J. Am. Chem. Soc. 110:1988;8734-8736.
25. Jefford C.W., Thornton S.R., Sienkiewicz K. Tetrahedron Lett. 35:1994;3905-3908.
26. Cooksey A.R., Morgan K.J., Morrey D.P. Tetrahedron. 1970;5101-5111.
27. Sonnet P.E. J. Org. Chem. 36:1971;1005-1007.
28. Olah G.A., Kuhn. J. Am. Chem. Soc. 83:1961;4564-4571.
29. (a) Paine J.B., Dolphin D. Can. J. Chem. 54:1976;411-414
30. (b) Thyrann T., Lightner D.A. Tetrahedron Lett. 36:1995;4345-4348
31. (c) Thyrann T., Lightner D.A.J. Heterocycl. Chem. 33:1996;221-222
32. (d) Thyrann T., Lightner D.A. Tetrahedron Lett. 37:1996;315-318.
33. Baciocchi E., Muraglia E., Sleiter G. J. Org. Chem. 57:1992;2486-2490.
34. Anderson N.G., Carson J.R. J. Med. Chem. 23:1980;98-100.
35. Almerico A.M., Cirrincione G., Aiello E., Dattolo G.J. Heterocycl. Chem. 26:1989;1631-1633.