CBI prodrug analogs of CC-1065 and the duocarmycins

Synthesis

Volumn , Issue SPEC. ISS., 1999, Pages 1505-1509

  Boger, Dale L ^a   Boyce, Christopher W ^a   Garbaccio, Robert M ^a   Searcey, Mark ^a   Jin, Qing ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

CBI indole2; Cytoxicity; Duocarmycins; Prodrugs

Indexed keywords

1,2,9,9A TETRAHYDROCYCLOPROPA[C]BENZ[E]INDOL 4 ONE; 3 [5' [[(1H INDOL 2'' YL)CARBONYL]AMINO] 1H INDOL 2' YL]CARBONYL] 1 (CHLOROMETHYL) 5 [[(4 METHYL 1 PIPERAZINYL)CARBONYL]OXY] 1,2 DIHYDRO 3H BENZ[E]INDOLE; 3 [5' [[(1H INDOL 2'' YL)CARBONYL]AMINO] 1H INDOL 2' YL]CARBONYL] 5 (ACETYLOXY) 1 (CHLOROMETHYL) 1,2 DIHYDRO 3H BENZ[E]INDOLE; ANTINEOPLASTIC AGENT; DUOCARMYCIN A; DUOCARMYCIN SA; INDOLE DERIVATIVE; PRODRUG; RACHELMYCIN; UNCLASSIFIED DRUG;

ALKYLATION; ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG HYDROLYSIS; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; LEUKEMIA L 1210; MOUSE; NONHUMAN; STRUCTURE ANALYSIS;

EID: 0032813670     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3658     Document Type: Article

References (28)

1. Boger, D. L.; Johnson, D. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1439. Boger, D. L.; Boyce, C. W., Garbaccio, R. M.; Goldberg, J. Chem. Rev. 1997, 97, 787. Boger, D. L.; Johnson, D. S. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 3642. Boger, D. L. Acc. Chem. Res. 1995, 28, 20. Boger, D. L. Chemtracts: Org. Chem. 1991, 4, 329.
2. Boger, D. L.; Johnson, D. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1439. Boger, D. L.; Boyce, C. W., Garbaccio, R. M.; Goldberg, J. Chem. Rev. 1997, 97, 787. Boger, D. L.; Johnson, D. S. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 3642. Boger, D. L. Acc. Chem. Res. 1995, 28, 20. Boger, D. L. Chemtracts: Org. Chem. 1991, 4, 329.
3. Boger, D. L.; Johnson, D. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1439. Boger, D. L.; Boyce, C. W., Garbaccio, R. M.; Goldberg, J. Chem. Rev. 1997, 97, 787. Boger, D. L.; Johnson, D. S. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 3642. Boger, D. L. Acc. Chem. Res. 1995, 28, 20. Boger, D. L. Chemtracts: Org. Chem. 1991, 4, 329.
4. Boger, D. L.; Johnson, D. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1439. Boger, D. L.; Boyce, C. W., Garbaccio, R. M.; Goldberg, J. Chem. Rev. 1997, 97, 787. Boger, D. L.; Johnson, D. S. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 3642. Boger, D. L. Acc. Chem. Res. 1995, 28, 20. Boger, D. L. Chemtracts: Org. Chem. 1991, 4, 329.
5. Boger, D. L.; Johnson, D. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1439. Boger, D. L.; Boyce, C. W., Garbaccio, R. M.; Goldberg, J. Chem. Rev. 1997, 97, 787. Boger, D. L.; Johnson, D. S. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 3642. Boger, D. L. Acc. Chem. Res. 1995, 28, 20. Boger, D. L. Chemtracts: Org. Chem. 1991, 4, 329.
6. Warpehoski, M. A.; Hurley, L. H. Chem. Res. Toxicol. 1988, 1, 315. Hurley, L. H.; Needham-VanDevanter, D. R. Acc. Chem. Res. 1986, 19, 230. Warpehoski, M. A. In Advances in DNA Sequence Specific Agents; Hurley, L. H., Ed.; JAI: Greenwich, CT, 1992; Vol. 1, p 217. Hurley, L. H.; Draves, P. H. In Molecular Aspects of Anticancer Drug-DNA Interactions; Neidle, S.; Waring, M., Eds.; CRC: Ann Arbor, 1993; Vol. 1, p 89. Aristoff, P. A. In Advances in Medicinal Chemistry; Maryanoff, B. E., Maryanoff, C. E., Eds; JAI; Greenwich, CT, 1993; Vol. 2, p 67. Warpchoski, M. A.; McGovren, P.; Mitchell, M. A. In Molecular Basis of Specificity in Nucleic Acid-Drug Interactions; Pullman, B.; Jortner, J.; Eds.; Kluwer: Dordrecht, The Netherlands, 1990; 531.
7. Warpehoski, M. A.; Hurley, L. H. Chem. Res. Toxicol. 1988, 1, 315. Hurley, L. H.; Needham-VanDevanter, D. R. Acc. Chem. Res. 1986, 19, 230. Warpehoski, M. A. In Advances in DNA Sequence Specific Agents; Hurley, L. H., Ed.; JAI: Greenwich, CT, 1992; Vol. 1, p 217. Hurley, L. H.; Draves, P. H. In Molecular Aspects of Anticancer Drug-DNA Interactions; Neidle, S.; Waring, M., Eds.; CRC: Ann Arbor, 1993; Vol. 1, p 89. Aristoff, P. A. In Advances in Medicinal Chemistry; Maryanoff, B. E., Maryanoff, C. E., Eds; JAI; Greenwich, CT, 1993; Vol. 2, p 67. Warpchoski, M. A.; McGovren, P.; Mitchell, M. A. In Molecular Basis of Specificity in Nucleic Acid-Drug Interactions; Pullman, B.; Jortner, J.; Eds.; Kluwer: Dordrecht, The Netherlands, 1990; 531.
8. Warpehoski, M. A.; Hurley, L. H. Chem. Res. Toxicol. 1988, 1, 315. Hurley, L. H.; Needham-VanDevanter, D. R. Acc. Chem. Res. 1986, 19, 230. Warpehoski, M. A. In Advances in DNA Sequence Specific Agents; Hurley, L. H., Ed.; JAI: Greenwich, CT, 1992; Vol. 1, p 217. Hurley, L. H.; Draves, P. H. In Molecular Aspects of Anticancer Drug-DNA Interactions; Neidle, S.; Waring, M., Eds.; CRC: Ann Arbor, 1993; Vol. 1, p 89. Aristoff, P. A. In Advances in Medicinal Chemistry; Maryanoff, B. E., Maryanoff, C. E., Eds; JAI; Greenwich, CT, 1993; Vol. 2, p 67. Warpchoski, M. A.; McGovren, P.; Mitchell, M. A. In Molecular Basis of Specificity in Nucleic Acid-Drug Interactions; Pullman, B.; Jortner, J.; Eds.; Kluwer: Dordrecht, The Netherlands, 1990; 531.
9. Warpehoski, M. A.; Hurley, L. H. Chem. Res. Toxicol. 1988, 1, 315. Hurley, L. H.; Needham-VanDevanter, D. R. Acc. Chem. Res. 1986, 19, 230. Warpehoski, M. A. In Advances in DNA Sequence Specific Agents; Hurley, L. H., Ed.; JAI: Greenwich, CT, 1992; Vol. 1, p 217. Hurley, L. H.; Draves, P. H. In Molecular Aspects of Anticancer Drug-DNA Interactions; Neidle, S.; Waring, M., Eds.; CRC: Ann Arbor, 1993; Vol. 1, p 89. Aristoff, P. A. In Advances in Medicinal Chemistry; Maryanoff, B. E., Maryanoff, C. E., Eds; JAI; Greenwich, CT, 1993; Vol. 2, p 67. Warpchoski, M. A.; McGovren, P.; Mitchell, M. A. In Molecular Basis of Specificity in Nucleic Acid-Drug Interactions; Pullman, B.; Jortner, J.; Eds.; Kluwer: Dordrecht, The Netherlands, 1990; 531.
10. Warpehoski, M. A.; Hurley, L. H. Chem. Res. Toxicol. 1988, 1, 315. Hurley, L. H.; Needham-VanDevanter, D. R. Acc. Chem. Res. 1986, 19, 230. Warpehoski, M. A. In Advances in DNA Sequence Specific Agents; Hurley, L. H., Ed.; JAI: Greenwich, CT, 1992; Vol. 1, p 217. Hurley, L. H.; Draves, P. H. In Molecular Aspects of Anticancer Drug-DNA Interactions; Neidle, S.; Waring, M., Eds.; CRC: Ann Arbor, 1993; Vol. 1, p 89. Aristoff, P. A. In Advances in Medicinal Chemistry; Maryanoff, B. E., Maryanoff, C. E., Eds; JAI; Greenwich, CT, 1993; Vol. 2, p 67. Warpchoski, M. A.; McGovren, P.; Mitchell, M. A. In Molecular Basis of Specificity in Nucleic Acid-Drug Interactions; Pullman, B.; Jortner, J.; Eds.; Kluwer: Dordrecht, The Netherlands, 1990; 531.
11. Warpehoski, M. A.; Hurley, L. H. Chem. Res. Toxicol. 1988, 1, 315. Hurley, L. H.; Needham-VanDevanter, D. R. Acc. Chem. Res. 1986, 19, 230. Warpehoski, M. A. In Advances in DNA Sequence Specific Agents; Hurley, L. H., Ed.; JAI: Greenwich, CT, 1992; Vol. 1, p 217. Hurley, L. H.; Draves, P. H. In Molecular Aspects of Anticancer Drug-DNA Interactions; Neidle, S.; Waring, M., Eds.; CRC: Ann Arbor, 1993; Vol. 1, p 89. Aristoff, P. A. In Advances in Medicinal Chemistry; Maryanoff, B. E., Maryanoff, C. E., Eds; JAI; Greenwich, CT, 1993; Vol. 2, p 67. Warpchoski, M. A.; McGovren, P.; Mitchell, M. A. In Molecular Basis of Specificity in Nucleic Acid-Drug Interactions; Pullman, B.; Jortner, J.; Eds.; Kluwer: Dordrecht, The Netherlands, 1990; 531.
12. Boger, D. L.; Ishizaki, T.; Wysocki, Jr, R. J.; Munk, S. A.; Kitos, P. A.; Suntornwat, O. J. Am. Chem. Soc. 1989, 111, 6461. Boger, D. L.; Ishizaki, T.; Kitos, P. A.; Suntomwat, O. J. Org. Chem. 1990, 55, 5824. Boger, D. L.; Yun, W.; Teegarden, B. R. J. Org. Chem. 1992, 57, 2873. Boger, D. L.; McKic, J. A. J. Org. Chem. 1995, 60, 1271.
13. Boger, D. L.; Ishizaki, T.; Wysocki, Jr, R. J.; Munk, S. A.; Kitos, P. A.; Suntornwat, O. J. Am. Chem. Soc. 1989, 111, 6461. Boger, D. L.; Ishizaki, T.; Kitos, P. A.; Suntomwat, O. J. Org. Chem. 1990, 55, 5824. Boger, D. L.; Yun, W.; Teegarden, B. R. J. Org. Chem. 1992, 57, 2873. Boger, D. L.; McKic, J. A. J. Org. Chem. 1995, 60, 1271.
14. Boger, D. L.; Ishizaki, T.; Wysocki, Jr, R. J.; Munk, S. A.; Kitos, P. A.; Suntornwat, O. J. Am. Chem. Soc. 1989, 111, 6461. Boger, D. L.; Ishizaki, T.; Kitos, P. A.; Suntomwat, O. J. Org. Chem. 1990, 55, 5824. Boger, D. L.; Yun, W.; Teegarden, B. R. J. Org. Chem. 1992, 57, 2873. Boger, D. L.; McKic, J. A. J. Org. Chem. 1995, 60, 1271.
15. Boger, D. L.; Ishizaki, T.; Wysocki, Jr, R. J.; Munk, S. A.; Kitos, P. A.; Suntornwat, O. J. Am. Chem. Soc. 1989, 111, 6461. Boger, D. L.; Ishizaki, T.; Kitos, P. A.; Suntomwat, O. J. Org. Chem. 1990, 55, 5824. Boger, D. L.; Yun, W.; Teegarden, B. R. J. Org. Chem. 1992, 57, 2873. Boger, D. L.; McKic, J. A. J. Org. Chem. 1995, 60, 1271.
16. Warpehoski, M. A. Tetrahedron Lett. 1986, 27, 4103.
17. Boger, D. L.; Ishizaki, T.;. Sakya, S. M.; Munk, S. A.; Kitos, P. A.; Jin, Q.; Besterman, J. M. Bioorg. Med. Chem. Lett. 1991, 1, 115. Boger, D. L.; Yun, W.; Han, N. Bioorg. Med. Chem. 1995, 3, 1429.
18. Boger, D. L.; Ishizaki, T.;. Sakya, S. M.; Munk, S. A.; Kitos, P. A.; Jin, Q.; Besterman, J. M. Bioorg. Med. Chem. Lett. 1991, 1, 115. Boger, D. L.; Yun, W.; Han, N. Bioorg. Med. Chem. 1995, 3, 1429.
19. Nagamura, S.; Kanda, Y.; Kobayashi, E.; Gomi, K.; Saito, H. Chem. Pharm. Bull. 1995, 43, 1530.
20. Asai, A.; Nagamura, S.; Saito, H. J. Am. Chem. Soc. 1994, 116, 4171. Yasuzawa, T.; Muroi, K.; Ichimura, M.; Takahashi, I.; Ogawa, T.; Takahashi, K.; Sano, H.; Saitoh, Y. Chem. Pharm. Bull. 1995, 43, 378. Nagamura, S.; Asai, A.; Kanda, Y.; Kobayashi, E.; Gomi, K.; Saito, H. Chem. Pharm. Bull. 1996, 44, 1723. Nagamura, S.; Kobayashi, E.; Gomi, K.; Saito, H. Bioorg. Med. Chem. 1996, 4, 1379. Nagamura, S.; Kobayashi, E.; Gomi, K.; Saito, H. Bioorg. Med. Chem. Lett. 1996, 6, 2147. Alberts, S. R.; Erlichman, C.; Reid, J. M.; Sloan, J. A.; Ames, M. M.; Richardson, R. L.; Goldberg, R. M.; Clin. Cancer Res. 1998, 4, 2111.
21. Asai, A.; Nagamura, S.; Saito, H. J. Am. Chem. Soc. 1994, 116, 4171. Yasuzawa, T.; Muroi, K.; Ichimura, M.; Takahashi, I.; Ogawa, T.; Takahashi, K.; Sano, H.; Saitoh, Y. Chem. Pharm. Bull. 1995, 43, 378. Nagamura, S.; Asai, A.; Kanda, Y.; Kobayashi, E.; Gomi, K.; Saito, H. Chem. Pharm. Bull. 1996, 44, 1723. Nagamura, S.; Kobayashi, E.; Gomi, K.; Saito, H. Bioorg. Med. Chem. 1996, 4, 1379. Nagamura, S.; Kobayashi, E.; Gomi, K.; Saito, H. Bioorg. Med. Chem. Lett. 1996, 6, 2147. Alberts, S. R.; Erlichman, C.; Reid, J. M.; Sloan, J. A.; Ames, M. M.; Richardson, R. L.; Goldberg, R. M.; Clin. Cancer Res. 1998, 4, 2111.
22. Asai, A.; Nagamura, S.; Saito, H. J. Am. Chem. Soc. 1994, 116, 4171. Yasuzawa, T.; Muroi, K.; Ichimura, M.; Takahashi, I.; Ogawa, T.; Takahashi, K.; Sano, H.; Saitoh, Y. Chem. Pharm. Bull. 1995, 43, 378. Nagamura, S.; Asai, A.; Kanda, Y.; Kobayashi, E.; Gomi, K.; Saito, H. Chem. Pharm. Bull. 1996, 44, 1723. Nagamura, S.; Kobayashi, E.; Gomi, K.; Saito, H. Bioorg. Med. Chem. 1996, 4, 1379. Nagamura, S.; Kobayashi, E.; Gomi, K.; Saito, H. Bioorg. Med. Chem. Lett. 1996, 6, 2147. Alberts, S. R.; Erlichman, C.; Reid, J. M.; Sloan, J. A.; Ames, M. M.; Richardson, R. L.; Goldberg, R. M.; Clin. Cancer Res. 1998, 4, 2111.
23. Asai, A.; Nagamura, S.; Saito, H. J. Am. Chem. Soc. 1994, 116, 4171. Yasuzawa, T.; Muroi, K.; Ichimura, M.; Takahashi, I.; Ogawa, T.; Takahashi, K.; Sano, H.; Saitoh, Y. Chem. Pharm. Bull. 1995, 43, 378. Nagamura, S.; Asai, A.; Kanda, Y.; Kobayashi, E.; Gomi, K.; Saito, H. Chem. Pharm. Bull. 1996, 44, 1723. Nagamura, S.; Kobayashi, E.; Gomi, K.; Saito, H. Bioorg. Med. Chem. 1996, 4, 1379. Nagamura, S.; Kobayashi, E.; Gomi, K.; Saito, H. Bioorg. Med. Chem. Lett. 1996, 6, 2147. Alberts, S. R.; Erlichman, C.; Reid, J. M.; Sloan, J. A.; Ames, M. M.; Richardson, R. L.; Goldberg, R. M.; Clin. Cancer Res. 1998, 4, 2111.
24. Asai, A.; Nagamura, S.; Saito, H. J. Am. Chem. Soc. 1994, 116, 4171. Yasuzawa, T.; Muroi, K.; Ichimura, M.; Takahashi, I.; Ogawa, T.; Takahashi, K.; Sano, H.; Saitoh, Y. Chem. Pharm. Bull. 1995, 43, 378. Nagamura, S.; Asai, A.; Kanda, Y.; Kobayashi, E.; Gomi, K.; Saito, H. Chem. Pharm. Bull. 1996, 44, 1723. Nagamura, S.; Kobayashi, E.; Gomi, K.; Saito, H. Bioorg. Med. Chem. 1996, 4, 1379. Nagamura, S.; Kobayashi, E.; Gomi, K.; Saito, H. Bioorg. Med. Chem. Lett. 1996, 6, 2147. Alberts, S. R.; Erlichman, C.; Reid, J. M.; Sloan, J. A.; Ames, M. M.; Richardson, R. L.; Goldberg, R. M.; Clin. Cancer Res. 1998, 4, 2111.
25. Asai, A.; Nagamura, S.; Saito, H. J. Am. Chem. Soc. 1994, 116, 4171. Yasuzawa, T.; Muroi, K.; Ichimura, M.; Takahashi, I.; Ogawa, T.; Takahashi, K.; Sano, H.; Saitoh, Y. Chem. Pharm. Bull. 1995, 43, 378. Nagamura, S.; Asai, A.; Kanda, Y.; Kobayashi, E.; Gomi, K.; Saito, H. Chem. Pharm. Bull. 1996, 44, 1723. Nagamura, S.; Kobayashi, E.; Gomi, K.; Saito, H. Bioorg. Med. Chem. 1996, 4, 1379. Nagamura, S.; Kobayashi, E.; Gomi, K.; Saito, H. Bioorg. Med. Chem. Lett. 1996, 6, 2147. Alberts, S. R.; Erlichman, C.; Reid, J. M.; Sloan, J. A.; Ames, M. M.; Richardson, R. L.; Goldberg, R. M.; Clin. Cancer Res. 1998, 4, 2111.
26. Li, L. H.; DeKoning, T. F.; Kelly, R. C.; Krueger, W. C.; McGovren, J. P.; Padbury, G. E.; Petzold, G. L.; Wallace, T. L.; Ouding, R. J.; Prairie, M. D.; Gebhard, I. Cancer Res. 1992, 52, 4904. Houghton, P. J.; Cheshire, P. J.; Hallman, J. D.; Houghton, J. A. Cancer Chemother. Pharmacol. 1995, 36, 45. Van Tellingen, O.; Nooijen, W. J.; Schaaf, L. J.; Van Der Valk, M.; Van Asperen, J.; Henrar, R. E. C.; Beijnen, J. H. Cancer Res. 1998, 58, 2410.
27. Li, L. H.; DeKoning, T. F.; Kelly, R. C.; Krueger, W. C.; McGovren, J. P.; Padbury, G. E.; Petzold, G. L.; Wallace, T. L.; Ouding, R. J.; Prairie, M. D.; Gebhard, I. Cancer Res. 1992, 52, 4904. Houghton, P. J.; Cheshire, P. J.; Hallman, J. D.; Houghton, J. A. Cancer Chemother. Pharmacol. 1995, 36, 45. Van Tellingen, O.; Nooijen, W. J.; Schaaf, L. J.; Van Der Valk, M.; Van Asperen, J.; Henrar, R. E. C.; Beijnen, J. H. Cancer Res. 1998, 58, 2410.
28. Li, L. H.; DeKoning, T. F.; Kelly, R. C.; Krueger, W. C.; McGovren, J. P.; Padbury, G. E.; Petzold, G. L.; Wallace, T. L.; Ouding, R. J.; Prairie, M. D.; Gebhard, I. Cancer Res. 1992, 52, 4904. Houghton, P. J.; Cheshire, P. J.; Hallman, J. D.; Houghton, J. A. Cancer Chemother. Pharmacol. 1995, 36, 45. Van Tellingen, O.; Nooijen, W. J.; Schaaf, L. J.; Van Der Valk, M.; Van Asperen, J.; Henrar, R. E. C.; Beijnen, J. H. Cancer Res. 1998, 58, 2410.