Chemistry of ecteinascidins. Part 3: Preparation of 2′-N-acyl derivatives of ecteinascidin 770 and evaluation of cytotoxicity

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 15, 2011, Pages 4421-4436

  Saktrakulkla, Panithi ^a   Toriumi, Satoru ^b   Tsujimoto, Mitsuhiro ^b   Patarapanich, Chamnan ^a   Suwanborirux, Khanit ^a   Saito, Naoki ^b  

^a CHULALONGKORN UNIVERSITY   (Thailand)

^b MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Cytotoxicity; Ecteinascidin; Marine natural product; Structure activity relationship study

Indexed keywords

2' N (3 NITROBENZOYL) ECTEINASCIDIN 770; 2' N (4 NITROBENZOYL) ECTEINASCIDIN 770; 2' N (4 NITROCINNAMOYL) ECTEINASCIDIN 770; 2' N (4 QUINOLINECARBONYL) ECTEINASCIDIN 770; 2' N (5 QUINOLINECARBONYL) ECTEINASCIDIN 770; 2' N (6 QUINOLINECARBONYL) ECTEINASCIDIN 770; 2' N (CINNAMOYL) ECTEINASCIDIN 770; 2' N (ISONICOTINYL) ECTEINASCIDIN 770; 2' N (NICOTINYL) ECTEINASCIDIN 770; 2' N ALLYL ECTEINASCIDIN 770; 2' N BENZOYL ECTEINASCIDIN 770; 2' N INDOLE 3 CARBONYL ECTEINASCIDIN 770; 6' O ALLYL ECTEINASCIDIN 770; AMIDE; CARBONYL DERIVATIVE; ECTEINASCIDIN 770; HETEROCYCLIC COMPOUND; ISOQUINOLINE DERIVATIVE; RENIERAMYCIN DERIVATIVE; SAFRAMYCIN; TRIALLYL ECTEINASCIDIN 770; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYTOTOXICITY; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; DRUG SCREENING ASSAYS, ANTITUMOR; HCT116 CELLS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; HUMANS; INHIBITORY CONCENTRATION 50; ISOQUINOLINES; NEOPLASMS; STRUCTURE-ACTIVITY RELATIONSHIP; UROCHORDATA;

EID: 79960559983     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.06.047     Document Type: Article

References (33)

1. J.D. Scott, and R.M. Williams Chem. Rev. 102 2002 1669
2. K.L. Rinehart Med. Drug Rev. 20 2000 1
3. R. Henriquez, G. Faircloth, and C. Cuevas G.M. Cragg, D.G. Kingston, D.J. Newman, Anticancer Agents from Natural Products 2005 Taylor & Francis New York 215 223
4. Ecteinascidin 743 (1a) has the international nonproprietary name of trabectedin, and is being developed under the trade name ″Yondelis.″
5. E.J. Corey, D.Y. Gin, and R.S. Kania J. Am. Chem. Soc. 118 1996 9202
6. E. Martinez, and E.J. Corey Org. Lett. 2 2000 993
7. A. Endo, A. Yanagisawa, M. Abe, S. Tohma, T. Kan, and T. Fukuyama J. Am. Chem. Soc. 124 2002 6552
8. J. Chen, M. Bois-Choussy, and J. Zhu J. Am. Chem. Soc. 128 2006 87
9. S. Zheng, C. Chan, T. Furuuchi, B.J.D. Wright, B. Zhou, Z.J. Gio, and S.J. Danishefsky Angew. Chem. Int. Edit. 45 2006 1754
10. D. Fishlock, and R.M. Williams J. Org. Chem. 73 2008 9594
11. Y. Ikeda, H. Idemoto, F. Hirayama, K. Yamamoto, K. Iwao, T. Asao, and T. Munakata J. Antibiot. 36 1983 1279
12. Y. Ikeda, H. Matsuki, T. Ogawa, and T. Munakata J. Antibiot. 36 1983 1284
13. Y. Ikeda, Y. Shimada, K. Honjo, T. Okumoto, and T. Munakata J. Antibiot. 36 1983 1290
14. T. Okumoto, M. Kawana, I. Nakamura, Y. Ikeda, and K. Isagai J. Antibiot. 38 1985 767
15. I. Ueda, S. Kawano, Y. Ikeda, H. Matsuki, and T. Ogawa Acta Crystallogr., Sect. C 40 1984 1578
16. E. Meyers, R. Cooper, W.H. Trejo, N. Georgopadakou, and R. Sykes J. Antibiot. 36 1983 190
17. R. Cooper, and S. Unoer J. Antibiot. 38 1985 24
18. C. Cuevas, M. Pérez, M.J. Martin, J.L. Chicharro, C. Fernández-Rivas, M. Flores, A. Francesch, P. Gallego, M. Zarzuelo, F. de la Calle, J. Garcia, C. Polanco, I. Rodríguez, and I. Manzanares Org. Lett. 2 2000 2545
19. C. Cuevas, and A. Francesch Nat. Prod. Rep. 26 2009 322
20. E.J. Martinez, T. Owa, S.L. Schreiber, and E.J. Corey Proc. Natl Acad. Sci. USA 96 1999 3496
21. J.W. Lane, A. Estevez, K. Mortara, O. Callan, J.L. Spencer, and R.M. Williams Bioorg. Med. Chem. Lett. 16 2006 3180
22. J.R. Spencer, M. Sendzik, J. Oeh, P. Sabbatini, S.A. Dalrymple, C. Magill, H.M. Kim, P. Zang, N. Squires, K.G. Moss, J. Sukbuntherng, A.G. Myers, and M.J. Green Bioorg. Med. Chem. Lett. 16 2006 4884
23. B.J. Wright, C. Chan, and S.L. Danishefsky J. Nat. Prod. 71 2008 409
24. J.F. Gonzlez, E. de la Cuesta, and C. Avendaño Bioorg. Med. Chem. 15 2007 112
25. Z.-Z. Liu, Y. Wang, Y.-F. Tang, S.-Z. Chen, X.-G. Chen, and H.-Y. Li Bioorg. Med. Chem. Lett. 16 2006 1282
26. K. Charupant, N. Daikuhara, E. Saito, S. Amnuoypol, K. Suwanborirux, T. Owa, and N. Saito Bioorg. Med. Chem. 17 2009 4548
27. W. Liu, W. Dong, X. Liao, Z. Yan, B. Guan, N. Wang, and Z. Liu Bioorg. Med. Chem. Lett. 21 2011 1419
28. R. Sakai, E.A. Jares-Erijman, I. Manzanares, M.V.S. Elipe, and K.L. Rinehart J. Am. Chem. Soc. 118 1996 9017
29. K. Suwanborirux, K. Charupant, S. Amnuoypol, S. Pummangura, A. Kubo, and N. Saito J. Nat. Prod. 65 2002 935
30. P. Puthongking, C. Patarapanich, S. Amnuoypol, K. Suwanborirux, A. Kubo, and N. Saito Chem. Pharm. Bull. 54 2006 1010
31. F. Guibé Tetrahedron 54 1998 2967
32. D.A. Evans, J.A. Ellman, and K.M. de Vries J. Am. Chem. Soc. 111 1989 8912
33. 1H NMR and MS measurements could be conducted (see, Experimental). It was proposed that the steric influence of the 18-O-allyl group might have hindered the deprotection reaction. When the reaction time (90 h) was prolonged both 5 and 18-O-allyl-2′-N-indole-3-carbonyl Et 770 were consumed in the reaction: however, the yield of 3 only 36.5%.