Synthesis of a bifunctional monophosphinate DOTA derivative having a free carboxylate group in the phosphorus side chain

Synthesis

Volumn , Issue 9, 2008, Pages 1431-1435

  Řezanka, Pavel ^a   Kubíček, Vojtěch ^a   Hermann, Petr ^a   Lukeš, Ivan ^a  

^a CHARLES UNIVERSITY   (Czech Republic)

Author keywords

Macrocycles; MRI contrast agents; Phosphinate ligands; Phosphorus; Radiopharmaceuticals

Indexed keywords

CARBOXYLATION; DERIVATIVES; DRUG PRODUCTS; LIGANDS; MAGNETIC RESONANCE IMAGING; RADIOTHERAPY;

CARBOXYLATE GROUPS; MACROCYCLES; PHOSPHINATE LIGANDS; RADIOPHARMACEUTICALS;

PHOSPHORUS COMPOUNDS;

1,4,7,10 TETRAAZACYCLODODECANE 1,4,7,10 TETRAACETIC ACID; 3 [HYDROXY[[4,7,10 TRIS[(TERT BUTOXYCARBONYL)METHYL] 1,4,7,10 TETRAAZACYCLODODECAN 1 YL]METHYL]PHOSPHORYL]PROPANOIC ACID; ACETIC ACID DERIVATIVE; ETHYL 3 [ETHOXY(MESYLOXYMETHYL)PHOSPHORYL]PROPANOATE; MONOPHOSPHINATE 1,4,7,10 TETRAAZACYCLODODECANE 1,4,7,10 TETRAACETIC ACID DERIVATIVE; PHOSPHINOPROPANOIC ACID DERIVATIVE; PROPIONIC ACID DERIVATIVE; TRI TERT BUTYL 1,4,7,10 TETRAAZACYCLODODECANE 1,4,7 TRIACETATE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOGRAPHY; COMPLEX FORMATION; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE IMAGING; PEPTIDE SYNTHESIS; SYNTHESIS;

EID: 44049087794     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1072571     Document Type: Article

References (36)

1. (a) Caravan, P. Chem. Soc. Rev. 2006, 35, 512.
2. (b) Aime, S.; Botta, M.; Terreno, E. Adv. Inorg. Chem. 2005, 57, 173.
3. (c) Topics in Current Chemistry, Vol. 221; Springer: Heidelberg, 2002.
4. (d) The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging; Merbach, A. E.; Tóth, É., Eds.; Wiley: Chichester, 2001.
5. (e) Caravan, P.; Ellison, J. J.; McMurry, T. J.; Lauffer, R. B. Chem. Rev. 1999, 99, 2293.
6. (a) Li, W. P.; Meyer, L. A.; Anderson, C. J. Top. Curr. Chem. 2005, 252, 179.
7. (b) Liu, S. Chem. Soc. Rev. 2004, 33, 445.
8. (c) Handbook of Radiopharmaceuticals. Radiochemistry and Applications; Welch, M. J.; Redvanly, C. S., Eds.; Wiley: Chichester, 2003.
9. (d) Liu, S.; Edwards, D. S. Bioconjugate Chem. 2001, 12, 7.
10. Denat, F.; Brandés, S.; Guilard, R. Synlett 2000, 561.
11. Rudovsky, J.; Cígler, P.; Kotek, J.; Hermann, P.; Vojtíšek, P.; Lukeš I.; Peters, J. A.; Elst, L. V.; Muller, R. N. Chem. Eur. J. 2005, 11, 2373.
12. Rudovský, J.; Kotek, J.; Hermann, P.; Lukeš, I.; Mainero, V.; Aime, S. Org. Biomol. Chem. 2005, 3, 112.
13. Lebdušková, P.; Hermann, P.; Helm, L.; Tóth, É.; Kotek, J.; Binnemans, K.; Rudovský, J.; Lukeš, I.; Merbach, A. E. Dalton Trans. 2007, 493.
14. Rudovský, J.; Botta, M.; Hermann, P.; Koridze, A.; Aime, S. Dalton Trans. 2006, 2323.
15. Táborský, P.; Lubal, P.; Havel, J.; Kotek, J.; Hermann, P.; Lukeš, I. Collect. Czech. Chem. Commun. 2005, 70, 1909.
16. Försterová, M.; Svobodová, I.; Lubal, P.; Táborský, P.; Kotek, J.; Hermann, P.; Lukeš, I. Dalton Trans. 2007, 535.
17. (a) Rudovský, J.; Botta, M.; Hermann, P.; Hardcastle, K. I.; Lukeš, I.; Aime, S. Bioconjugate Chem. 2006, 17, 975.
18. (b) Rudovsky, J.; Hermann, P.; Botta, M.; Aime, S.; Lukeš, I. Chem. Commun. 2005, 2390.
19. Försterová, M.; Petrík, M.; Láznič ková, A.; Lázníček, M.; Hermann, P.; Lukeš, I.; Melichar, F. Appl. Radiat. Isotop. 2008, submitted.
20. (a) Broan, C. J.; Cole, E.; Jankowski, K. J.; Parker, D.; Pulukkody, K.; Boyce, B. A.; Beeley, N. R. A.; Millar, K.; Millican, A. T. Synthesis 1992, 63.
21. (b) Li, X.; Zhang, S.; Zhao, P.; Kovacs, Z.; Sherry, A. D. Inorg. Chem. 2001, 40, 6572.
22. (c) Chavez, M. R.; Zhao, P.; Kovacs, Z.; Sherry, A. D. Lett. Org. Chem. 2004, 1, 194.
23. (a) Fitch, S. J. J. Am. Chem. Soc. 1964, 86, 61.
24. (b) Pinnich, H. W.; Reynolds, M. A. Synth. Commun. 1979, 9, 535.
25. (c) Stawinski, J.; Thelin, M.; Westman, E.; Zain, R. J. Org. Chem. 1990, 55, 3505.
26. Maier, L. Helv. Chim. Acta 1973, 56, 489.
27. Montchamp, J.-L. J. Organomet. Chem. 2005, 690, 2388.
28. Deprele, S.; Montchamp, J.-L. J. Organomet. Chem. 2002, 643-644, 154.
29. Wróblewski, A. E.; Verkade, J. G. J. Am. Chem. Soc. 1996, 118, 10168.
30. (a) Issleib, K.; Mögelin, W.; Balszuweit, A. Z. Anorg. Allg. Chem. 1985, 530, 16.
31. (b) Boyd, E. A.; Corless, M.; James, K.; Regan, A. C. Tetrahedron Lett. 1990, 31, 2933.
32. (c) Boyd, E. A.; Regan, A. C.; James, K. Tetrahedron Lett. 1994, 35, 4223.
33. Kaestle, K. L.; Anwer, M. K.; Audhya, T. K.; Goldstein, G. Tetrahedron Lett. 1991, 32, 327.
34. Kafarski, P.; Lejczak, B. In Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity; Kukhar, V. P.; Hudson, H. R., Eds.; Wiley: Chichester, 2000, 173-203.
35. Dadabhoy, A.; Faulkner, S.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 2 2002, 348.
36. Petrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 4th. ed.; Pergamon Press: Oxford, 1988.