Synthesis and cytotoxicity of amino-seco-DSA: An amino analogue of the DNA alkylating agent duocarmycin SA

Journal of Organic Chemistry

Volumn 64, Issue 16, 1999, Pages 5946-5953

  Tercel, Moana ^a   Gieseg, Michael A ^a   Denny, William A ^a   Wilson, William R ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

DUOCARMYCIN SA; METHYL 5 AMINO 1 (CHLOROMETHYL) 3 [(5,6,7 TRIMETHOXYINDOL 2 YL)CARBONYL] 1,2 DIHYDRO 3H PYRROLO[3,2]INDOLE 7 CARBOXYLIC ACID; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CONFORMATIONAL TRANSITION; CYTOTOXICITY; DNA ALKYLATION; DRUG CONFORMATION; DRUG DNA BINDING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; NONHUMAN; STRUCTURE ACTIVITY RELATION;

EID: 0033529886     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990464j     Document Type: Article

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23. Previous syntheses of duocarmycin SA: (a) Boger, D. L.; Machiya, K.; Hertzog, D. L.; Kitos, P. A.; Holmes, D. J. Am. Chem. Soc. 1993, 115, 9025. (b) Muratake, H.; Abe, I.; Natsume, M. Chem. Pharm. Bull. 1996, 44, 67. (c) Muratake, H.; Tonegawa, M.; Natsume, M. Chem. Pharm. Bull. 1998, 46, 400. (d) Muratake, H.; Matsumura, N.; Natsume, M. Chem. Pharm. Bull. 1998, 46, 559. (e) Fukuda, Y.; Terashima, S. Tetrahedron Lett. 1997, 38, 7207. For a concise synthesis of an oxaduocarmycin SA analogue, see: (f) Patel, V. F.; Andis, S. L.; Enkema, J. K.; Johnson, D. A.; Kennedy, J. H.; Mohamadi, F.; Schultz, R. M.; Soose, D. J.; Spees, M. M. J. Org. Chem. 1997, 62, 8868. See also: (g) Muratake, H.; Okabe, K.; Takahashi, M.; Tonegawa, M.; Natsume, M. Chem. Pharm. Bull. 1997, 45, 799.
24. Previous syntheses of duocarmycin SA: (a) Boger, D. L.; Machiya, K.; Hertzog, D. L.; Kitos, P. A.; Holmes, D. J. Am. Chem. Soc. 1993, 115, 9025. (b) Muratake, H.; Abe, I.; Natsume, M. Chem. Pharm. Bull. 1996, 44, 67. (c) Muratake, H.; Tonegawa, M.; Natsume, M. Chem. Pharm. Bull. 1998, 46, 400. (d) Muratake, H.; Matsumura, N.; Natsume, M. Chem. Pharm. Bull. 1998, 46, 559. (e) Fukuda, Y.; Terashima, S. Tetrahedron Lett. 1997, 38, 7207. For a concise synthesis of an oxaduocarmycin SA analogue, see: (f) Patel, V. F.; Andis, S. L.; Enkema, J. K.; Johnson, D. A.; Kennedy, J. H.; Mohamadi, F.; Schultz, R. M.; Soose, D. J.; Spees, M. M. J. Org. Chem. 1997, 62, 8868. See also: (g) Muratake, H.; Okabe, K.; Takahashi, M.; Tonegawa, M.; Natsume, M. Chem. Pharm. Bull. 1997, 45, 799.
25. Previous syntheses of duocarmycin SA: (a) Boger, D. L.; Machiya, K.; Hertzog, D. L.; Kitos, P. A.; Holmes, D. J. Am. Chem. Soc. 1993, 115, 9025. (b) Muratake, H.; Abe, I.; Natsume, M. Chem. Pharm. Bull. 1996, 44, 67. (c) Muratake, H.; Tonegawa, M.; Natsume, M. Chem. Pharm. Bull. 1998, 46, 400. (d) Muratake, H.; Matsumura, N.; Natsume, M. Chem. Pharm. Bull. 1998, 46, 559. (e) Fukuda, Y.; Terashima, S. Tetrahedron Lett. 1997, 38, 7207. For a concise synthesis of an oxaduocarmycin SA analogue, see: (f) Patel, V. F.; Andis, S. L.; Enkema, J. K.; Johnson, D. A.; Kennedy, J. H.; Mohamadi, F.; Schultz, R. M.; Soose, D. J.; Spees, M. M. J. Org. Chem. 1997, 62, 8868. See also: (g) Muratake, H.; Okabe, K.; Takahashi, M.; Tonegawa, M.; Natsume, M. Chem. Pharm. Bull. 1997, 45, 799.
26. Previous syntheses of duocarmycin SA: (a) Boger, D. L.; Machiya, K.; Hertzog, D. L.; Kitos, P. A.; Holmes, D. J. Am. Chem. Soc. 1993, 115, 9025. (b) Muratake, H.; Abe, I.; Natsume, M. Chem. Pharm. Bull. 1996, 44, 67. (c) Muratake, H.; Tonegawa, M.; Natsume, M. Chem. Pharm. Bull. 1998, 46, 400. (d) Muratake, H.; Matsumura, N.; Natsume, M. Chem. Pharm. Bull. 1998, 46, 559. (e) Fukuda, Y.; Terashima, S. Tetrahedron Lett. 1997, 38, 7207. For a concise synthesis of an oxaduocarmycin SA analogue, see: (f) Patel, V. F.; Andis, S. L.; Enkema, J. K.; Johnson, D. A.; Kennedy, J. H.; Mohamadi, F.; Schultz, R. M.; Soose, D. J.; Spees, M. M. J. Org. Chem. 1997, 62, 8868. See also: (g) Muratake, H.; Okabe, K.; Takahashi, M.; Tonegawa, M.; Natsume, M. Chem. Pharm. Bull. 1997, 45, 799.
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