Selective protection of 1,4,8,11-tetraazacyclotetradecane (cyclam) in position 1,4 with the phosphonothioyl group and synthesis of a cyclam-1,4-bis(methylphosphonic acid). Crystal structures of several cyclic phosphonothioamides

Collection of Czechoslovak Chemical Communications

Volumn 71, Issue 3, 2006, Pages 337-367

  Vitha, Tomáš ^a   Kotek, Jan ^a   Rudovský, Jakub ^a   Kubíček, Vojtěch ^a   Císařová, Ivana ^a   Hermann, Petr ^a   Lukes, Ivan ^a  

^a CHARLES UNIVERSITY   (Czech Republic)

Author keywords

Aminophosphonic acids; Azacrown; Azacycle; Crystal structure determination; Cyclam; Cyclam cis protection; Cyclen; Macrocyclic ligands; Phosphonate ligands; Radiopharmaceuticals; TETP; Thiophosphonic amides

Indexed keywords

EID: 33744727759     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc20060337     Document Type: Article

References (62)

1. a) Merbach A. E., Toth E. (Eds): The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging. Wiley, Chichester 2001;
2. b) Krause W. (Ed.): Topics in Current Chemistry. Vol. 221, Springer Verlag, Heidelberg 2002;
3. c) Caravan P., Ellison J. J., Mc Murry T. J., Laufer R. B.: Chem. Rev. 1999, 99, 2293.
4. a) Li W. P., Meyer L. A., Anderson C. J.: Top. Curr. Chem. 20O5, 252, 179;
5. b) Liu S.: Chem. Soc. Rev. 2004, 33, 445;
6. c) Welch M. J., Redvanly C. S. (Eds): Handbook of Radiopharmaceuticals. Radiochemistry and Applications. Wiley, Chichester 2003;
7. d) Liu S., Edwards D. S.: Bioconjugate Chem. 2001, 12, 7.
8. a) Faulkner S., Matthews J. L. in: Comprehensive Coordination Chemistry II (J. A. McCleverty and T. J. Meyer, Eds), Vol. 9, p. 913. Elsevier, Amsterdam 2004;
9. b) Parker D., Dickins R. S., Puschmann H., Crossland C., Howard J. A. K.: Chem. Rev. 2002, 102, 1977.
10. a) Epstein D. M., Chappell L. L., Khalili H., Supkowski R. M., Horrocks W. DeW., Jr., Morrow J. R.: Inorg. Chem. 2000, 39, 2130;
11. b) Huang L., Chappell L. L., Khalili H., Iranzo O., Baker B. F., Morrow J. R.: J. Inorg. Biol. Chem. 2000, 5, 85.
12. a) Kurosaki H., Bucher C., Espinosa E., Barbe J.-M., Guilard R.: Inorg. Chim. Acta 2001, 322, 145;
13. b) Bucher C., Duval E., Barbe J.-M., Verpeaux J.-N., Amatore C., Guilard R.: C. R. Acad. Sci., Ser. IIc, Chem. 2000, 3, 211;
14. c) Chapman J., Ferguson G., Gallagher J. F., Jennings M. C., Parker D.: J. Chem. Soc., Dalton Trans. 1992, 345;
15. d) Helps I. M., Parker D., Chapman J., Ferguson G.: J. Chem. Soc., Chem. Commun. 1988, 1094.
16. a) Woodin K. S., Heroux K. J., Boswell C. A., Wong E. H., Weisman G. R., Niu W., Tomellini S. A., Anderson C. J., Zakharov L. N., Rheingold A. L.: Eur. J. Inorg. Chem. 2005, 4829;
17. b) Boswell C. A., Sun X., Niu W., Weisman G. R., Wong E. H., Rheingold A. L., Anderson C. J.: J. Med. Chem. 2004, 47, 1465;
18. c) Lichty J., Allen S. M., Grillo A. I., Archibald S. J., Hubin T. J.: Inorg. Chim. Acta 2004, 357, 615.
19. a) Tonei D. M., Ware D. C., Brothers P. J., Plieger P. G., Clark G. R.: Dalton Trans. 2006, 152;
20. b) Tonei D. M., Baker L.-J., Brothers P. J., Clark G. R., Ware D. C.: Chem. Commun. 1998, 2593;
21. c) Ware D. C., Tonei D. M., Baker L.-J., Brothers P. J., Clark G. R.: Chem. Commun. 1996, 1303.
22. a) Batsanov A. S., Goeta A. E., Howard J. A. K., Maffeo D., Puschmann H., Williams J. A. G.: Polyhedron 2001, 20, 981;
23. b) Goeta A. E., Howard J. A. K., Maffeo D., Puschmann H., Williams J. A. G., Yufit D. S.: J. Chem. Soc., Dalton Trans. 2000, 1873;
24. c) Davies P. J., Taylor M. R., Wainwright K. P.: Chem. Commun. 1998, 827.
25. a) Royal G., Dahaoui-Gindrey V., Dahaoui S., Tabard A., Guilard R., Pullumbi P., Lecomte C.: Eur. J. Org. Chem. 1998, 1971;
26. b) Bucher C., Royal G., Barbe J.-M., Guilard R.: Tetrahedron Lett. 1999, 40, 2315.
27. Kotek J., Hermann P., Vojtíšek P., Rohovec J., Lukeš I.: Collect. Czech. Chem. Commun. 2000, 65, 243.
28. Lukeš I., Kotek J., Vojtíšek P., Hermann P.: Coord. Chem. Rev. 2001, 216-217, 287.
29. Kotek J., Vojtíšek P., Cisařová I., Hermann P., Jurečka P., Rohovec J., Lukeš I.: Collect. Czech. Chem. Commun. 2000, 65, 1289.
30. Kotek J., Vojtíšek P., Císařová I., Hermann P., Lukeš I.: Collect. Czech. Chem. Commun. 2001, 66, 363.
31. Kotek J., Cisařová I., Hermann P., Lukeš I., Rohovec J.: Inorg. Chim. Acta 2001, 317, 324.
32. Kotek J., Lubal P., Hermann P., Císařová I., Lukeš I., Godula T., Svobodová I., Táborský P., Havel J.: Chem. Eur. J. 20O3, 9, 233.
33. Svobodová I., Lubal P., Plutnar J., Havlíč ková J., Kotek J., Hermann P., Lukeš I.: J. Chem. Soc., Dalton Trans. submitted.
34. a) Svobodová I., Lubal P., Hermann P., Kotek J., Havel J.: J. Inclusion Phenom. Macrocycl. Chem. 2004, 49, 11;
35. b) Svobodová I., Lubal P., Hermann P., Kotek J., Havel J.: Microchim. Acta 2004, 148, 21.
36. Barefield E. K., Wagner F., Hodges K. D.: Inorg. Chem. 1976, 15, 1370.
37. Cronin L., Mount A. R., Parsons S., Robertson N.: J. Chem. Soc., Dalton Trans. 1999, 1925.
38. a) Bellouard F., Chuburu F., Kervarec N., Toupet L., Triki S., Mest Y. L., Handel H.: J. Chem. Soc., Perkin Trans. 1 1999, 3499;
39. b) Krajewski J. W., Gluzinski P., Kolinski R. A., Kemme A., Mishnev A.: Pol. J. Chem. 1994, 68, 703.
40. Batsanov A. S., Bruce J. I., Ganesh T., Low P. J., Kataky R., Puschmann H., Steel P. G.: J. Chem. Soc., Perkin Trans 1 2002, 932.
41. Prevote D., Donnadieu B., Moreno-Manas M., Caminade A. M., Majoral J. P.: Eur. J. Org. Chem. 1999, 1701.
42. Tebby J. C. (Ed.): CRC Handbook of Phosphorus-31 Nuclear Magnetic Resonance Data. CRC Press, Boca Raton 1991.
43. Meyer M., Dahaoui-Gindrey V., Lecomte C., Guilard R.: Coord. Chem. Rev. 1998, 178-180, 1313.
44. a) Krysiak J., Lyon C., Baceiredo A., Gornitzka H., Mikolajzyk M., Bertrand G.: Chem. Eur. J. 2004, 10, 1982;
45. b) Zablocka M., Igau A., Cenac N., Donnadieu B., Dahan F., Majoral J. P., Pietrusiewicz M. K.: J. Am. Chem Soc. 1995, 117, 8083.
46. a) Gardinier I., Roignant A., Oget N., Bernard H., Yaouanc J.-J., Handel H.: Tetrahedron Lett. 1996, 37, 7711;
47. b) Oget N., Chuburu F., Yaouanc J.-J., Handel H.: Tetrahedron Lett. 1996, 8, 2995;
48. c) Filali A., Yaouanc J.-J., Handel H.: Angew. Chem., Int. Ed. Engl. 1991, 30, 560.
49. Fuzerová S., Kotek J., Císařová I., Hermann P., Binnemans K., Lukeš I.: Dalton Trans. 2005, 2908.
50. a) Delgado R., Siegfried L. C., Kaden T. A.: Helv. Chim. Acta 1990, 73, 140;
51. b) Pisareva S. A., Belskii F. I., Medved T. Ya., Kabachnik I. M.: Izv. Akad. Nauk SSSR, Ser. Khim. 1987, 413.
52. Havlíčková J., Vitha T., Kotek J., Kubíček V., Hermann P., Lukeš I.: Unpublished results.
53. a) Barefield E. K., Wagner F., Herbinger A. W., Dahl A. R.: Inorg. Synth. 1976, 17, 220;
54. b) Meunier I., Mishra A. K., Hanquet B., Cocolis P., Guilard R.: Can. J. Chem. 1995, 73, 685.
55. Patel N. K., Harwood H. J.: J. Org. Chem. 1967, 32, 2999.
56. Perrin D. D., Armarego W. L. F.: Purification of Laboratory Chemicals, 3rd ed., Pergamon Press, Oxford 1988.
57. Sun X., Wuest M., Kovacz Z., Sherry A. D., Motekaitis R., Wang Z., Martell A. E., Welch M. J., Anderson C. J.: J. Biol. Inorg. Chem. 2003, 8, 217.
58. Füzerová S.: Unpublished results.
59. Otwinovski Z., Minor W.: HKL DENZO and Scalepack Program Package. Nonius BV, Delft 1997;
60. see also Otwinovski Z., Minor W.: Methods Enzymol. 1997, 276, 307.
61. Altomare A., Burla M. C., Camalli M., Cascarano G., Giacovazzo C., Guagliardi A., Polidori G.: J. Appl. Crystallogr. 1994, 27, 435.
62. Sheldrick G. M.: SHELXL97. Program for Crystal Structure Refinement from Diffraction Data. University of Göttingen, Göttingen 1997.