Design, synthesis, and biological evaluation of novel C14-C3′BzN- linked macrocyclic taxoids

Journal of Organic Chemistry

Volumn 73, Issue 24, 2008, Pages 9584-9593

  Sun, Liang ^a   Geng, Xudong ^a   Geney, Raphaël ^a   Li, Yuan ^a   Simmerling, Carlos ^a   Li, Zhong ^a   Lauher, Joseph W ^a   Xia, Shujun ^b   Horwitz, Susan B ^b   Veith, Jean M ^c   Pera, Paula ^c   Bernacki, Ralph J ^c   Ojima, Iwao ^a  

^a STONY BROOK UNIVERSITY   (United States)

^b ALBERT EINSTEIN COLLEGE OF MEDICINE   (United States)

^c ROSWELL PARK CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE COMPOUNDS; BENZOYL GROUPS; BIOACTIVE CONFORMATIONS; BIOLOGICAL ACTIVITIES; BIOLOGICAL EVALUATIONS; CLOSING METATHESES; COMPUTATIONAL ANALYSES; CONFORMATIONAL CHANGES; COUPLING PROCESSES; HIGH SENSITIVITIES; KEY COMPONENTS; MACROCYCLIC; ORTHO POSITIONS; PACLITAXEL; RCM REACTIONS; STRUCTURE-ACTIVITY RELATIONSHIPS; TAXOIDS; TUMOR CELLS;

AMIDES; BIOCHEMISTRY; CELL GROWTH; GROWTH KINETICS; POLYMERS;

OPTICAL DEVICES;

1 (2 ALKENYLBENZOYL)BETA LACTAM; 1 (2 ALLYBENZOYL) 3 TRIETHYLSILOXY 4 PHENYLAZETIDIN 2 ONE; 1 (2 ALLYLBENZOYL) 3 TRIISOPROPYLSILOXY 4 (2 METHYLPROP 1 ENYL)AZETIDIN 2 ONE; 1 (2 ALLYLOXYBENZOYL) 3 TRIETHYLSILOXY 4 PHENYLAZETIDIN 2 ONE; 1 (2 ETHYLBENZOYL) 3 TRIETHYLSILOXY 4 PHENYLAZETIDIN 2 ONE; 14BETA ALLYLOXY 3'N DEBENZOYL 3'N(2 ALLYLBENZOYL) 7,2' TRIETHYLSILYLPACLITAXEL; 14BETA ALLYLOXY 3'N DEBENZOYL 3'N(2 ALLYLOXYBENZOYL) 7,2' TRIETHYLSILYPACLITAXEL; 14BETA ALLYLOXY 3'N DEBENZOYL 3'N(2 ETHENYLBENZOYL) 7,2' TRIETHYLSILYPACLITAXEL; 14BETA ALLYLOXY 7 TRIETHYLSILYBACCATIN III; 3 TERT BUTYLDIMETHYLSILOXY 4 (2 METHYLPROPEN 2 YL)AZETIDIN 2 ONE; 3 TRIETHYLSILOXY 4 PHENYLAZETIDIN 2 ONE; 3 TRIIOSOPROPYLSILOXY 4 PHENYLAZETIDINE ONE; 7 TRIETHYLSILYL 14BETA ALLYLOXY 2' TRIISOPROPYL 3' DEPHENYL 3' (2 METHYLPROP 1 ENYL) 3'N DEBENZOYL 3'N (2 ALLYLBENZOYL)PACLITAXEL; 7 TRIETHYLSILYL 14BETA HYDROBACCATIN III; 7,2' DISILYPACLITAXEL DIENE DERIVATIVE; ANTINEOPLASTIC AGENT; PACLITAXEL; RUTHENIUM; SB T 0253; SB T 2054; SB T 2061; TAXOID; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL CULTURE; CANCER CHEMOTHERAPY; CANCER INHIBITION; CATALYSIS; CELL ASSAY; CHEMICAL REACTION; CHEMOSENSITIVITY; COMPUTER MODEL; CONTROLLED STUDY; DRUG CONFORMATION; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MICROTUBULE ASSEMBLY; MOLECULAR MIMICRY; RING CLOSING METATHESIS; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; CELL LINE, TUMOR; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INDICATORS AND REAGENTS; MACROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MICROSCOPY, ELECTRON; MICROTUBULES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; TAXOIDS; TUBULIN;

EID: 58049221274     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801713q     Document Type: Article

References (42)

1. Jemal, A.; Ward, E.; Hao, Y.; Thun, M. JAMA, J. Am. Med. Assoc. 2005, 294, 1255-1259.
2. Jemal, A.; Siegel, R.; Ward, E.; Murray, T.; Xu, J.; Smigal, C.; Thun Michael, J. Ca - Cancer J. Clin. 2006, 56, 106-130.
3. Rowinsky, E. K. Ann. Rev. Med. 1997, 48, 353-374.
4. Suffness, M., Ed. Taxol: Science and Applications, 1995.
5. Schiff, P. B.; Fant, J.; Horwitz, S. B. Nature 1979, 277, 665-667.
6. Schiff, P. B.; Horwitz, S. B. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 1561-1565.
7. Kingston, D. G. I.; Bane, S.; Snyder, J. P. Cell Cycle 2005, 4, 279-289.
8. Geney, R.; Sun, L.; Pera, P.; Bernacki, R. J.; Xia, S.; Horwitz, S. B.; Simmerling, C. L.; Ojima, I. Chem. Biol. 2005, 12, 339-348.
9. Dubois, J.; Guenard, D.; Gueritte-Voegelein, F.; Guedira, N.; Potier, P.; Gillet, B.; Beloeil, J. C. Tetrahedron 1993, 49, 6533-6544.
10. Williams, H. J.; Scott, A. I.; Dieden, R. A.; Swindell, C. S.; Chirlian, L. E.; Francl, M. M.; Heerding, J. M.; Krauss, N. E. Tetrahedron 1993, 49, 6545-6560.
11. Vander Velde, D. G.; Georg, G. I.; Grunewald, G. L.; Gunn, C. W.; Mitscher, L. A. J. Am. Chem. Soc. 1993, 115, 11650-11651.
12. Mastropaolo, D.; Camerman, A.; Luo, Y.; Brayer, G. D.; Camerman, N. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 6920-6924.
13. Ojima, I.; Kuduk, S. D.; Chakravarty, S.; Ourevitch, M.; Bégué, J.-P. J. Am. Chem. Soc. 1997, 119, 5519-5527.
14. Ojima, I.; Lin, S.; Inoue, T.; Miller, M. L.; Borella, C. P.; Geng, X.; Walsh, J. J. J. Am. Chem. Soc. 2000, 122, 5343-5353.
15. Ojima, I.; Zucco, M.; Duclos, O.; Kuduk, S. D.; Sun, C.-M.; Park, Y. H. Bioorg. Med. Chem. Lett. 1993, 3, 2479-2482.
16. Geng, X.; Miller, M. L.; Lin, S.; Ojima, I. Org. Lett. 2003, 5, 3733-3736.
17. Nogales, E.; Wolf, S. G.; Downing, K. H. Nature 1998, 391, 199-203.
18. Lowe, J.; Li, H.; Downing, K. H.; Nogales, E. J. Mol. Bol. 2001, 313, 1045-1057.
19. Snyder, J. P.; Nettles, J. H.; Comett, B.; Downing, K. H.; Nogales, E. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 5312-5316.
20. Ganesh, T.; Guza, R. C.; Bane, S.; Ravindra, R.; Shanker, N.; Lakdawala, A. S.; Snyder, J. P.; Kingston, D. G. I. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 10006-10011.
21. Querolle, O. D., J.; Thoret, S.; Roussi, F.; Gueritte, F.; Guénard, D. J. Med. Chem. 2004, 47, 5937-5944.
22. Ganesh, T.; Yang, C.; Norris, A.; Glass, T.; Bane, S.; Ravindra, R.; Banerjee, A.; Metaferia, B.; Thomas, S. L.; Giannakakou, P.; Alcaraz, A. A.; Lakdawala, A. S.; Snyder, J. P.; Kingston, D. G. I. J. Med. Chem. 2007, 50, 713-725.
23. Larroque, A.-L.; Dubois, J.; Thoret, S.; Aubert, G.; Chiaroni, A.; Gueritte, F.; Guenard, D. Bioorg. Med. Chem. 2007, 15, 563-574.
24. Li, Y.; Poliks, B.; Cegelski, L.; Poliks, M.; Cryczynski, A.; Piszcek, G.; Jagtap, P. G.; Studelska, D. R.; Kingston, D. G. I.; Schaefer, J.; Bane, S. Biochemistry 2000, 39, 281-291.
25. Rao, S.; He, L.; Chakravarty, S.; Ojima, I.; Orr, G. A.; Horwitz, S. B. J. Biol. Chem. 1999, 274, 37990-37994.
26. Paik, Y.; Yang, C.; Metaferia, B.; Tang, S.; Bane, S.; Ravindra, R.; Shanker, N.; Alcaraz, A. A.; Johnson, S. A.; Schaefer, J.; O'Connor, R. D.; Cegelski, L.; Snyder, J. P.; Kingston, D. G. I. J. Am. Chem. Soc. 2007, 129, 361-370.
27. Ojima, I.; Slater, J. C.; Michaud, E.; Kuduk, S. D.; Bounaud, P.-Y.; Vrignaud, P.; Bissery, M.-C.; Veith, J.; Pera, P.; Bernacki, R. J. J. Med. Chem. 1996, 39, 3889-3896.
28. Ojima, I.; Chen, J.; Sun, L.; Borella, C. P.; Wang, T.; Miller, M. L.; Lin, S.; Geng, X.; Kuznetsova, L. V.; Qu, C.; Gallager, D.; Zhao, X.; Zanardi, I.; Xia, S.; Horwtiz, S. B.; Mallen-St. Clair, J.; Guerriero, J. L.; Bar-Sagi, D.; Veith, J. M.; Pera, P.; Bernacki, R. J. J. Med. Chem. 2008, 51, 3203-3221.
29. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
30. Ojima, I.; Habus, I.; Zhao, M.; Zucco, M.; Park, Y. H.; Sun, C. M.; Brigaud, T. Tetrahedron 1992, 48, 6985-7012.
31. Ojima, I. Acc. Chem. Res. 1995, 28, 383-389, and references cited therein.
32. Ojima, I.; Chakravarty, S.; Inoue, T.; Lin, S.; He, L.; Horwitz, S. B.; Kuduk, S. D.; Danishefsky, S. J. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 4256-4261.
33. Ojima, I.; Geng, X.; Lin, S.; Pera, P.; Bernacki, R. J. Bioorg. Med. Chem. Lett. 2002, 12, 349-352.
34. Reich, S. H.; Melnick, M.; Pino, M. J.; Fuhry, M. A. M.; Trippe, A. J.; Appelt, K.; Davies, J. F.; Wu, B. W.; Musick, L. J. Med. Chem. 1996, 39, 2781-2794.
35. Chang, S.; Grubbs, R. H. J. Org. Chem. 1998, 63, 864-866.
36. Kim, B. M.; Park, J. K. Bull. Korean Chem. Soc. 1999, 20, 744-746.
37. Holton, R. A.; Zhang, Z.; Clarke, P. A.; Nadizadeh, H.; Procter, D. J. Tetrahedron Lett. 1998, 39, 2883-2886.
38. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R. J. Nat. Cancer Inst. 1990, 82, 1107-1112.
39. Motulsky, H. J.; Ransnas, L. A. FASEB J. 1987, 1, 365-74.
40. Weisenberg, R. C. Science 1972, 177, 1104-1105.
41. Shelanski, M. L.; Gaskin, F.; Cantor, C. R. Proc. Natl. Acad. Sci. U.S.A. 1973, 70, 765-768.
42. Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. J. Am. Chem. Soc. 1990, 112, 6127-9.