A new synthetic method of all carboxylate-free DTPA derivatives and its application to the synthesis of Gd-carborane complex

Tetrahedron Letters

Volumn 37, Issue 4, 1996, Pages 539-542

  Nemoto, Hisao ^a   Cai, Jianping ^b   Yamamoto, Yoshinori ^b  

^a INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GADOLINIUM PENTETATE; PENTETIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030071278     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02235-X     Document Type: Article

References (29)

1. Recent example: Lanthanide-cyclodextrin complexes; Wenzel, T. J.; Bogyo, M. S.; Lebeau, E. L. J.Am. Chem. Soc., 1994, 116, 4858. Gadolinium complexes: Sieving, P. F.; Watson, A. D.; Rocklage, S. M. Bioconjugate Chem., 1990, 1, 65. Terbium complex: Bailey, M. P.; Rocks,. B. F.; Riley C. Analyst, 1984, 109, 1449. Indium complexes: Paik, C. H.; Sood, V. K.; Le, N.; Cioloca, L.; Carrasquillo, J. A.; Reynolds, J. C.; Neumann, R. D.; Rega, R.C. Nucl. Med. Biol., 1992, 19, 517. Technetium complexes: Aldenhoff, Y. B. J.; van Kroonenburg, M. J. P. G.; Zimny, S. V. M.; Menheere, P. P. C. A.; Koole, L. H. J. Chem. Soc. Chem. Commun. 1995, 523.
2. Recent example: Lanthanide-cyclodextrin complexes; Wenzel, T. J.; Bogyo, M. S.; Lebeau, E. L. J.Am. Chem. Soc., 1994, 116, 4858. Gadolinium complexes: Sieving, P. F.; Watson, A. D.; Rocklage, S. M. Bioconjugate Chem., 1990, 1, 65. Terbium complex: Bailey, M. P.; Rocks,. B. F.; Riley C. Analyst, 1984, 109, 1449. Indium complexes: Paik, C. H.; Sood, V. K.; Le, N.; Cioloca, L.; Carrasquillo, J. A.; Reynolds, J. C.; Neumann, R. D.; Rega, R.C. Nucl. Med. Biol., 1992, 19, 517. Technetium complexes: Aldenhoff, Y. B. J.; van Kroonenburg, M. J. P. G.; Zimny, S. V. M.; Menheere, P. P. C. A.; Koole, L. H. J. Chem. Soc. Chem. Commun. 1995, 523.
3. Recent example: Lanthanide-cyclodextrin complexes; Wenzel, T. J.; Bogyo, M. S.; Lebeau, E. L. J.Am. Chem. Soc., 1994, 116, 4858. Gadolinium complexes: Sieving, P. F.; Watson, A. D.; Rocklage, S. M. Bioconjugate Chem., 1990, 1, 65. Terbium complex: Bailey, M. P.; Rocks,. B. F.; Riley C. Analyst, 1984, 109, 1449. Indium complexes: Paik, C. H.; Sood, V. K.; Le, N.; Cioloca, L.; Carrasquillo, J. A.; Reynolds, J. C.; Neumann, R. D.; Rega, R.C. Nucl. Med. Biol., 1992, 19, 517. Technetium complexes: Aldenhoff, Y. B. J.; van Kroonenburg, M. J. P. G.; Zimny, S. V. M.; Menheere, P. P. C. A.; Koole, L. H. J. Chem. Soc. Chem. Commun. 1995, 523.
4. Recent example: Lanthanide-cyclodextrin complexes; Wenzel, T. J.; Bogyo, M. S.; Lebeau, E. L. J.Am. Chem. Soc., 1994, 116, 4858. Gadolinium complexes: Sieving, P. F.; Watson, A. D.; Rocklage, S. M. Bioconjugate Chem., 1990, 1, 65. Terbium complex: Bailey, M. P.; Rocks,. B. F.; Riley C. Analyst, 1984, 109, 1449. Indium complexes: Paik, C. H.; Sood, V. K.; Le, N.; Cioloca, L.; Carrasquillo, J. A.; Reynolds, J. C.; Neumann, R. D.; Rega, R.C. Nucl. Med. Biol., 1992, 19, 517. Technetium complexes: Aldenhoff, Y. B. J.; van Kroonenburg, M. J. P. G.; Zimny, S. V. M.; Menheere, P. P. C. A.; Koole, L. H. J. Chem. Soc. Chem. Commun. 1995, 523.
5. Recent example: Lanthanide-cyclodextrin complexes; Wenzel, T. J.; Bogyo, M. S.; Lebeau, E. L. J.Am. Chem. Soc., 1994, 116, 4858. Gadolinium complexes: Sieving, P. F.; Watson, A. D.; Rocklage, S. M. Bioconjugate Chem., 1990, 1, 65. Terbium complex: Bailey, M. P.; Rocks,. B. F.; Riley C. Analyst, 1984, 109, 1449. Indium complexes: Paik, C. H.; Sood, V. K.; Le, N.; Cioloca, L.; Carrasquillo, J. A.; Reynolds, J. C.; Neumann, R. D.; Rega, R.C. Nucl. Med. Biol., 1992, 19, 517. Technetium complexes: Aldenhoff, Y. B. J.; van Kroonenburg, M. J. P. G.; Zimny, S. V. M.; Menheere, P. P. C. A.; Koole, L. H. J. Chem. Soc. Chem. Commun. 1995, 523.
6. 2H group appears to be necessary for efficient renal excretion of an anion by the dianionic pathway; Despopoulos, A. J. Theor. Biol. 1965, 8, 163.
7. 2H group appears to be necessary for efficient renal excretion of an anion by the dianionic pathway; Despopoulos, A. J. Theor. Biol. 1965, 8, 163.
8. 2H group appears to be necessary for efficient renal excretion of an anion by the dianionic pathway; Despopoulos, A. J. Theor. Biol. 1965, 8, 163.
9. 2H group appears to be necessary for efficient renal excretion of an anion by the dianionic pathway; Despopoulos, A. J. Theor. Biol. 1965, 8, 163.
10. 2H group appears to be necessary for efficient renal excretion of an anion by the dianionic pathway; Despopoulos, A. J. Theor. Biol. 1965, 8, 163.
11. Various electrophiles (benzyl bromide, methyl iodide, butyl iodide, acrolein, 4-cyanobenzyl bromide, and allyl bromide) in the presence of bases (LDA, NaHMDS, KHMDS) were examined, but complex mixture of products due to poly-alkylation and poly-ester-condensation were obtained.
12. When NaHMDS was used instead of KHMDS, yield of 8 was increased. The structure of 8 was not clear because the position, at which the second ester group attached, could not be determined.
13. 2Et, was obtained as a by-product.
14. Tsuji, J.; Pure and Appl. Chem., 1982, 54, 197.
15. The palladium catalyzed reaction with allylic acetate did not give the desired product 10.
16. This choice of the catalyst combination gives often better results as reported in our recent papers. Nemoto, H.; Rong, F.-G.; Yamamoto, Y. J. Org. Chem., 1990, 55, 6065. Nemoto, H.; Cai, J.; Yamamoto, Y. J. Chem. Soc., Chem. Commun., 1994, 577.
17. This choice of the catalyst combination gives often better results as reported in our recent papers. Nemoto, H.; Rong, F.-G.; Yamamoto, Y. J. Org. Chem., 1990, 55, 6065. Nemoto, H.; Cai, J.; Yamamoto, Y. J. Chem. Soc., Chem. Commun., 1994, 577.
18. Whittaker, A. D.; Kelly, D. P.; Pardee, M.; Martin, R.F. Progress in Neutron Capture Therapy for Cancer. Ed. by Allen B.J. et at., Plenum Press, New York, 1992, p231.
19. For an excellent review, Hawthorn. M. F. Angew. Chem. Internat. Ed. Engl. 1993, 32, 950. Our recent papers on BNCT. Yamamoto, Y.; Seko, T.; Nemoto, H.; Hojo, Mukai N.; Hashimoto, Y. J. Chem. Soc., Chem. Commun., 1992, 157. Yamamoto, Y.; Seko, T.; Nakamura H.; Nemoto, H. Heteroatom Chem., 1992, 3, 239. Nemoto, H.; Wilson, J. G.; Nakamura H.; Yamamoto, Y. J. Org. Chem., 1992, 57, 435. Yamamoto, Y.; Asao, N.; Meguro, M.; Tsukada, N.; Nemoto, H.; Sadayori, N.; Wilson, J. G.; Nakamura, H. J. Chem. Soc., Chem. Commun., 1993, 1201. Yamamoto, Y.; Nakamura, H. J. Med. Chem., 1993, 36, 2232. Yamamoto, Y.; Takamatsu, S.; Nakamura, H. J. Mag. Res. Ser. B, 1993, 101, 198. Nemoto, H.; Cai, J.; Yamamoto, Y. J. Chem. Soc., Chem. Commun., 1994, 577. Nakamura, H.; Sadayori, N.; Sekido, M.; Yamamoto, Y. J. Chem. Soc. Chem. Common., 1994, 2581.
20. For an excellent review, Hawthorn. M. F. Angew. Chem. Internat. Ed. Engl. 1993, 32, 950. Our recent papers on BNCT. Yamamoto, Y.; Seko, T.; Nemoto, H.; Hojo, Mukai N.; Hashimoto, Y. J. Chem. Soc., Chem. Commun., 1992, 157. Yamamoto, Y.; Seko, T.; Nakamura H.; Nemoto, H. Heteroatom Chem., 1992, 3, 239. Nemoto, H.; Wilson, J. G.; Nakamura H.; Yamamoto, Y. J. Org. Chem., 1992, 57, 435. Yamamoto, Y.; Asao, N.; Meguro, M.; Tsukada, N.; Nemoto, H.; Sadayori, N.; Wilson, J. G.; Nakamura, H. J. Chem. Soc., Chem. Commun., 1993, 1201. Yamamoto, Y.; Nakamura, H. J. Med. Chem., 1993, 36, 2232. Yamamoto, Y.; Takamatsu, S.; Nakamura, H. J. Mag. Res. Ser. B, 1993, 101, 198. Nemoto, H.; Cai, J.; Yamamoto, Y. J. Chem. Soc., Chem. Commun., 1994, 577. Nakamura, H.; Sadayori, N.; Sekido, M.; Yamamoto, Y. J. Chem. Soc. Chem. Common., 1994, 2581.
21. For an excellent review, Hawthorn. M. F. Angew. Chem. Internat. Ed. Engl. 1993, 32, 950. Our recent papers on BNCT. Yamamoto, Y.; Seko, T.; Nemoto, H.; Hojo, Mukai N.; Hashimoto, Y. J. Chem. Soc., Chem. Commun., 1992, 157. Yamamoto, Y.; Seko, T.; Nakamura H.; Nemoto, H. Heteroatom Chem., 1992, 3, 239. Nemoto, H.; Wilson, J. G.; Nakamura H.; Yamamoto, Y. J. Org. Chem., 1992, 57, 435. Yamamoto, Y.; Asao, N.; Meguro, M.; Tsukada, N.; Nemoto, H.; Sadayori, N.; Wilson, J. G.; Nakamura, H. J. Chem. Soc., Chem. Commun., 1993, 1201. Yamamoto, Y.; Nakamura, H. J. Med. Chem., 1993, 36, 2232. Yamamoto, Y.; Takamatsu, S.; Nakamura, H. J. Mag. Res. Ser. B, 1993, 101, 198. Nemoto, H.; Cai, J.; Yamamoto, Y. J. Chem. Soc., Chem. Commun., 1994, 577. Nakamura, H.; Sadayori, N.; Sekido, M.; Yamamoto, Y. J. Chem. Soc. Chem. Common., 1994, 2581.
22. For an excellent review, Hawthorn. M. F. Angew. Chem. Internat. Ed. Engl. 1993, 32, 950. Our recent papers on BNCT. Yamamoto, Y.; Seko, T.; Nemoto, H.; Hojo, Mukai N.; Hashimoto, Y. J. Chem. Soc., Chem. Commun., 1992, 157. Yamamoto, Y.; Seko, T.; Nakamura H.; Nemoto, H. Heteroatom Chem., 1992, 3, 239. Nemoto, H.; Wilson, J. G.; Nakamura H.; Yamamoto, Y. J. Org. Chem., 1992, 57, 435. Yamamoto, Y.; Asao, N.; Meguro, M.; Tsukada, N.; Nemoto, H.; Sadayori, N.; Wilson, J. G.; Nakamura, H. J. Chem. Soc., Chem. Commun., 1993, 1201. Yamamoto, Y.; Nakamura, H. J. Med. Chem., 1993, 36, 2232. Yamamoto, Y.; Takamatsu, S.; Nakamura, H. J. Mag. Res. Ser. B, 1993, 101, 198. Nemoto, H.; Cai, J.; Yamamoto, Y. J. Chem. Soc., Chem. Commun., 1994, 577. Nakamura, H.; Sadayori, N.; Sekido, M.; Yamamoto, Y. J. Chem. Soc. Chem. Common., 1994, 2581.
23. For an excellent review, Hawthorn. M. F. Angew. Chem. Internat. Ed. Engl. 1993, 32, 950. Our recent papers on BNCT. Yamamoto, Y.; Seko, T.; Nemoto, H.; Hojo, Mukai N.; Hashimoto, Y. J. Chem. Soc., Chem. Commun., 1992, 157. Yamamoto, Y.; Seko, T.; Nakamura H.; Nemoto, H. Heteroatom Chem., 1992, 3, 239. Nemoto, H.; Wilson, J. G.; Nakamura H.; Yamamoto, Y. J. Org. Chem., 1992, 57, 435. Yamamoto, Y.; Asao, N.; Meguro, M.; Tsukada, N.; Nemoto, H.; Sadayori, N.; Wilson, J. G.; Nakamura, H. J. Chem. Soc., Chem. Commun., 1993, 1201. Yamamoto, Y.; Nakamura, H. J. Med. Chem., 1993, 36, 2232. Yamamoto, Y.; Takamatsu, S.; Nakamura, H. J. Mag. Res. Ser. B, 1993, 101, 198. Nemoto, H.; Cai, J.; Yamamoto, Y. J. Chem. Soc., Chem. Commun., 1994, 577. Nakamura, H.; Sadayori, N.; Sekido, M.; Yamamoto, Y. J. Chem. Soc. Chem. Common., 1994, 2581.
24. For an excellent review, Hawthorn. M. F. Angew. Chem. Internat. Ed. Engl. 1993, 32, 950. Our recent papers on BNCT. Yamamoto, Y.; Seko, T.; Nemoto, H.; Hojo, Mukai N.; Hashimoto, Y. J. Chem. Soc., Chem. Commun., 1992, 157. Yamamoto, Y.; Seko, T.; Nakamura H.; Nemoto, H. Heteroatom Chem., 1992, 3, 239. Nemoto, H.; Wilson, J. G.; Nakamura H.; Yamamoto, Y. J. Org. Chem., 1992, 57, 435. Yamamoto, Y.; Asao, N.; Meguro, M.; Tsukada, N.; Nemoto, H.; Sadayori, N.; Wilson, J. G.; Nakamura, H. J. Chem. Soc., Chem. Commun., 1993, 1201. Yamamoto, Y.; Nakamura, H. J. Med. Chem., 1993, 36, 2232. Yamamoto, Y.; Takamatsu, S.; Nakamura, H. J. Mag. Res. Ser. B, 1993, 101, 198. Nemoto, H.; Cai, J.; Yamamoto, Y. J. Chem. Soc., Chem. Commun., 1994, 577. Nakamura, H.; Sadayori, N.; Sekido, M.; Yamamoto, Y. J. Chem. Soc. Chem. Common., 1994, 2581.
25. For an excellent review, Hawthorn. M. F. Angew. Chem. Internat. Ed. Engl. 1993, 32, 950. Our recent papers on BNCT. Yamamoto, Y.; Seko, T.; Nemoto, H.; Hojo, Mukai N.; Hashimoto, Y. J. Chem. Soc., Chem. Commun., 1992, 157. Yamamoto, Y.; Seko, T.; Nakamura H.; Nemoto, H. Heteroatom Chem., 1992, 3, 239. Nemoto, H.; Wilson, J. G.; Nakamura H.; Yamamoto, Y. J. Org. Chem., 1992, 57, 435. Yamamoto, Y.; Asao, N.; Meguro, M.; Tsukada, N.; Nemoto, H.; Sadayori, N.; Wilson, J. G.; Nakamura, H. J. Chem. Soc., Chem. Commun., 1993, 1201. Yamamoto, Y.; Nakamura, H. J. Med. Chem., 1993, 36, 2232. Yamamoto, Y.; Takamatsu, S.; Nakamura, H. J. Mag. Res. Ser. B, 1993, 101, 198. Nemoto, H.; Cai, J.; Yamamoto, Y. J. Chem. Soc., Chem. Commun., 1994, 577. Nakamura, H.; Sadayori, N.; Sekido, M.; Yamamoto, Y. J. Chem. Soc. Chem. Common., 1994, 2581.
26. For an excellent review, Hawthorn. M. F. Angew. Chem. Internat. Ed. Engl. 1993, 32, 950. Our recent papers on BNCT. Yamamoto, Y.; Seko, T.; Nemoto, H.; Hojo, Mukai N.; Hashimoto, Y. J. Chem. Soc., Chem. Commun., 1992, 157. Yamamoto, Y.; Seko, T.; Nakamura H.; Nemoto, H. Heteroatom Chem., 1992, 3, 239. Nemoto, H.; Wilson, J. G.; Nakamura H.; Yamamoto, Y. J. Org. Chem., 1992, 57, 435. Yamamoto, Y.; Asao, N.; Meguro, M.; Tsukada, N.; Nemoto, H.; Sadayori, N.; Wilson, J. G.; Nakamura, H. J. Chem. Soc., Chem. Commun., 1993, 1201. Yamamoto, Y.; Nakamura, H. J. Med. Chem., 1993, 36, 2232. Yamamoto, Y.; Takamatsu, S.; Nakamura, H. J. Mag. Res. Ser. B, 1993, 101, 198. Nemoto, H.; Cai, J.; Yamamoto, Y. J. Chem. Soc., Chem. Commun., 1994, 577. Nakamura, H.; Sadayori, N.; Sekido, M.; Yamamoto, Y. J. Chem. Soc. Chem. Common., 1994, 2581.
27. For an excellent review, Hawthorn. M. F. Angew. Chem. Internat. Ed. Engl. 1993, 32, 950. Our recent papers on BNCT. Yamamoto, Y.; Seko, T.; Nemoto, H.; Hojo, Mukai N.; Hashimoto, Y. J. Chem. Soc., Chem. Commun., 1992, 157. Yamamoto, Y.; Seko, T.; Nakamura H.; Nemoto, H. Heteroatom Chem., 1992, 3, 239. Nemoto, H.; Wilson, J. G.; Nakamura H.; Yamamoto, Y. J. Org. Chem., 1992, 57, 435. Yamamoto, Y.; Asao, N.; Meguro, M.; Tsukada, N.; Nemoto, H.; Sadayori, N.; Wilson, J. G.; Nakamura, H. J. Chem. Soc., Chem. Commun., 1993, 1201. Yamamoto, Y.; Nakamura, H. J. Med. Chem., 1993, 36, 2232. Yamamoto, Y.; Takamatsu, S.; Nakamura, H. J. Mag. Res. Ser. B, 1993, 101, 198. Nemoto, H.; Cai, J.; Yamamoto, Y. J. Chem. Soc., Chem. Commun., 1994, 577. Nakamura, H.; Sadayori, N.; Sekido, M.; Yamamoto, Y. J. Chem. Soc. Chem. Common., 1994, 2581.
28. Maurer. J. L.; Berchier, F.; Serino, A. J.; Knobler, C. B.; Hawthorne, M. F. J. Org. Chem. 1990, 55, 838
29. Sodium or potassium hydroxide did not work well.