Regioselectivity and nucleophilic control in the cyclopropane ring opening of duocarmycin SA derivatives under neutral and acid conditions: A quantum mechanical study in the gas phase and in solution

Journal of Organic Chemistry

Volumn 69, Issue 22, 2004, Pages 7414-7422

  Cimino, Paola ^a,b   Gomez Paloma, Luigi ^b   Barone, Vincenzo ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b UNIVERSITY OF SALERNO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTICS; DNA; METHANOL; SUBSTRATES;

ANTITUMOR ANTIBIOTICS; NUCLEOPHILIC CONTROL;

QUANTUM THEORY;

ANTINEOPLASTIC ANTIBIOTIC; CYCLOPROPANE; DNA; DUOCARMYCIN SA; DUOCARMYCIN SA DERIVATIVE; METHANOL; METHYLAMINE; NITROGEN; OXYGEN; PYRIDINE; RACHELMYCIN; SOLVENT; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; DENSITY FUNCTIONAL THEORY; DNA ALKYLATION; ELECTRON; ENERGY; GAS; HARDNESS; PH; QUANTUM MECHANICS; RING OPENING; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

CYCLOPROPANES; INDOLES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PYRIDINES; PYRROLES; STEREOISOMERISM; THERMODYNAMICS;

EID: 6344278411     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049178k     Document Type: Article

References (32)

1. Boger, D. L.; Johnson, D. L. Angew. Chem., Int. Ed. Engl. 1996, 35, 1438-1474.
2. Boger, D. L.; Hertzog, D. L.; Bollinger B.; Johnson, D. L.; Cai H.; Goldberg, J.; Turnbull, P. J. Am. Chem. Soc. 1997, 119, 4977-4986.
3. Boger, D. L.; Bollinger B.; Hertzog, D. L.; Johnson, D. L.; Cai H.; Mesini, P.; Garbaccio, R. M.; Jin, Q.; Kitos, P. A. J. Am. Chem. Soc. 1997, 119, 4987-4998.
4. Baraldi, P. G.; Balboni, G.; Pavani, M. G.; Spalluto, G.; Tabrizi, M. A.; De Clercq, E.; Balzarini, J.; Bando, T.; Sugiyama, H.; Romagnoli, R. J. Med. Chem. 2001, 44, 2536-2543.
5. Nagamura, S.; Asai, A.; Kobayashi, E.; Gomi, K.; Saito, H. Bioorg. Med. Chem. 1997, 5, 623-630.
6. Amishiro, N.; Nagamura, S.; Kobayashi, E.; Okamoto, A.; Gomi, K.; Okabe, M.; Saito, H. Bioorg. Med. Chem. 2000, 8, 1637-1643.
7. Boger, D. L.; Goldberg, J. A.; McKie, A. Bioorg. Med. Chem. Lett. 1996, 6, 1955-1960.
8. Boger, D. L.; Santillan, A., Jr.; Searcey, M.; Jin, Q. J. Org. Chem. 1999, 64, 5241-5244.
9. Boger, D. L.; Wysocki, R. J., Jr.; Ishizaki, T. J. Am. Chem. Sac. 1980, 112, 5230-5240.
10. Boger, D. L.; Mesini, P. J. Am. Chem. Soc. 1904, 116, 11335-11348.
11. Cimino, P.; Improta, R.; Bifulco, G.; Riccio, R.; Gomez-Paloma, L.; Barone, V. J. Org. Chem. 2004, 69, 2816-2824.
12. Boger, D. L.; Santillan, A., Jr.; Searcey, M.; Jin, Q. J. Am. Chem. Soc, 1998, 120, 11554-11557.
13. Boger, D. L.; Garbaccio, R. M. J. Org. Chem. 1999, 64, 5666-5669.
14. Boger, D. L.; Boyce, C. W.; Johnson, D. L. Bioorg. Med. Chem. Lett. 1997, 7, 233-238.
15. Ambroise, Y.; Boger, D. L. Bioorg. Med. Chem. Lett. 2002, 12, 303-306.
16. Adamo, C.; Barone, V. J. Chem. Phys. 1999, 110, 6158-6170.
17. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Chem. Phys. 2002, 117, 43-54.
18. Ciofini, I.; Hazebroueq, S.; Joubert, L.; Adamo, C. Theor. Chem. Acc. 2004, 111, 188-195.
19. Parr, R. G.; Szentpaly, L.; Liu, S. J. Am. Chem. Soc. 1999, 121, 1922-1924.
20. Boger, D. L.; Goldberg, J.; McKe, J. A. Bioorg. Med. Chem. Lett. 1996, 6, 1955-1960.
21. Roy, R. K; Pal, S.; Hirao, K. J. Phys. Chem. 1999, 110, 8236-8245.
22. Roy, R. K; Hirao, K.; Pal, S. J. Phys. Chem. 2000, 113, 1372-1379.
23. Gaussian 03, Revision B.4: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Durant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratehian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Parkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K; Foresman, J. B.; Ortiz, J. V.; Gui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 2003.
24. A description of basis sets and standard computational methods can be found in: Foresman, J. B.; Frisch, A. E. Exploring Chemistry with Electronic Structure Methods, 2nd ed.; Gaussian Inc., Pittsburgh, PA, 1996.
25. Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027.
26. Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 16, 1170-1176.
27. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926.
28. Chermette, H. J. Comput. Chem. 1999, 20, 129-154.
29. Parr, R.; Pearson, R. G. J. Am. Chem. Soc. 1983, 105, 7512-7516.
30. Pearson, R. G. Chemical Hardness; VCH: Weinheim, 1997.
31. Hirshfeld, F. L. Theor. Chim. Acta 1977, 44, 129-131.
32. Warpehoski, M. A.; Harper, D. E. J. Am. Chem. Soc. 1994,116, 7573-7580.