Synthesis of a metal-free texaphyrin

Organic Letters

Volumn 3, Issue 24, 2001, Pages 3911-3914

  Hannah, Sharon ^a   Lynch, Vincent M ^a   Gerasimchuk, Nikolay ^b   Magda, Darren ^b   Sessler, Jonathan L ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^b PHARMACYCLICS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

METAL; PORPHYRIN; TEXAPHYRIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; METALS; MOLECULAR STRUCTURE; PORPHYRINS; SPECTROPHOTOMETRY, ULTRAVIOLET; SUPPORT, NON-U.S. GOV'T; SUPPORT, U.S. GOV'T, P.H.S.;

EID: 0035969602     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016757s     Document Type: Article

References (23)

1. Sessler, J. L.; Murai, T.; Lynch, V.; Cyr, M. J. Am. Chem. Soc. 1988, 110, 5586-5588.
2. Sessler, J. L.; Johnson, M. R.; Lynch, V. J. Org. Chem. 1987, 52, 4394-4397.
3. (a) Sessler, J. L.; Hemmi, G.; Mody, T. D.; Murai, T.; Burrell, A.; Young, S. W. Acc. Chem. Res. 1994, 27, 43-50.
4. (b) Sessler, J. L.; Mody, T. D.; Hemmi, G. W.; Lynch, V. Inorg. Chem. 1993, 32, 3175-3187.
5. Sessler, J. L.; Tvermoes, N. A.; Guldi, D. M.; Mody, T. D.; Allen, W. E. J. Phys. Chem. A 1999, 103, 787-794.
6. (a) Rosenthal, D. L; Nurenberg, P.; Becerra, C. R.; Frenkel, E. P.; Carbone, D. P.; Lum, B. L.; Miller, R.; Engel, J.; Young, S.; Miles, D.; Renschler, M. F. Clin. Cancer Res. 1999, 5, 739-745.
7. (b) Viala, J.; Vanel, D.; Meingan, P.; Lartigau, E.; Carde, P.; Renschler, M. Radiology 1999, 212, 755-759.
8. (c) Carde, P.; Timmerman, R.; Mehta, M. P.; Koprowski, C. D.; Ford, J.; Tishler, R. B.; Miles, D.; Miller, R. A.; Renschler, M. F. J. Clin. Onc. 2001, 19, 2074-2083.
9. Shimanovich, R.; Hannah, S.; Lynch, V.; Gerasimchuk, N.; Mody, T. D.; Magda, D.; Sessler, J.; Groves, J. T. J. Am. Chem Soc. 2001, 123, 3613-3614.
10. Sessler, J. L.; Murai, T.; Lynch, V. Inorg. Chem. 1989, 28, 1333-1341.
11. CRC Handbook of Chemistry and Physics, 63rd ed.; Weast, R. C., Astle, M. J., Eds.; CRC Press: Boca Raton, FL, 1982.
12. + produced by oxidation of 1. Since the acid-salt. 4, is recovered from the reaction, presumably 3 is a stronger base than lutidine.
13. 6: C, 58.68; H, 5.80; N, 10.07, Found: C, 58.53; H, 5.77; N, 10.27.
14. 3 -texaphyrin stoichiometry but at a higher concentration was found to increase the yield of 5 at the account of 4.
15. 2: C, 48.52; H, 4.91; N, 8.32. Found: C, 49.88; H, 4.95; N, 8.12.
16. 3), 8.67 (2H, s, H-aryl), 9.23 (2H, s, meso-H), 11.02 (2H, s, imine.)
17. Sessler, J. L.; Brucker, E. A.; Lynch, V.; Choe, M.; Sorey, S.; Vogel, E. Chem. Eur. J. 1996, 2, 1527-1532.
18. Sessler, J. L.; Weghorn, S. J. Expanded, Contracted, and Isomeric Porphyrins; Elsevier: Oxford, 1497.
19. 2OEP, leads to an upfield shift of 10.6 ppm for the NH protons; see: (a) Whitlock, H. W., Jr.; Buchanan, D. H. Tetrahedron Lett. 1969, 42, 3711-3714.
20. (b) Scheer, H.; Katz, J. J. In Porphyrins and Metalloporphyrins; Smith, K., Ed.; Elsevier: Amsterdam, 1975; Chapter 10.
21. Gong, L.-C: Dolphin, D. Can. J. Chem. 1985, 63, 401-405.
22. Magda, D.; Lepp, C.; Gerasimchuk, N.; Sessler, J. L.; Lin, A.; Biaglow, J.; Miller, R. A. Int. J. Radiat. Oncol., Biol., Phys. In press.
23. Unpublished results.