Synthesis of pyridine-based polyaminocarboxylic ligands bearing a thioalkyl anchor

Tetrahedron Letters

Volumn 48, Issue 19, 2007, Pages 3463-3466

  Lin, Yi ^a   Favre Réguillon, Alain ^b   Pellet Rostaing, Stéphane ^a   Lemaire, Marc ^a  

^a UNIVERSITÉ LYON 1   (France)

^b Bioinformatique et Chimie Moléculaire   (France)

Author keywords

Azamacrocycle; Mitsunobu reaction; PCTA; Thiol

Indexed keywords

2,4 DIHYDROXYMETHYL 3 HYDROXYPYRIDINE; 3 HYDROXYPYRIDINE; ACETIC ACID; CHELATING AGENT; LIGAND; PENTETIC ACID DERIVATIVE; POLYAMINOACID; PYRIDINE DERIVATIVE; TETRAAZATRIACETIC ACID; TRITYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DEPROTECTION REACTION; MITSUNOBU REACTION; SYNTHESIS;

EID: 34247274095     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.03.024     Document Type: Article

References (40)

1. Rohrer M., Bauer H., Mintorovitch J., Requardt M., and Weinmann H.-J. Invest. Radiol. 40 (2005) 715-724
2. Vincent J., and Desreux J.-F. Top. Curr. Chem. 221 (2002) 123-164
3. Caravan P., Ellison J.J., McMurry T.J., and Lauffer R.B. Chem. Rev. 99 (1999) 2293-2352
4. Aime S., Fasano M., and Terreno E. Chem. Soc. Rev. 27 (1998) 19-29
5. Wiener E.C., Brechbiel M.W., Brothers H., Magin R.L., Gansow O.A., Tomalia D.A., and Lauterbur P.C. Magn. Reson. Med. 3 (1994) 1-8
6. Toth E., Pubanz D., Vauthey S., Helm L., and Merbach A.E. Chem. Eur. J. 2 (1996) 1607-1615
7. Aime S., Botta M., Garino E., Geninatti Crich S., Giovenzana G., Pagliarin R., Palmisano G., and Sisti M. Chem. Eur. J. 6 (2000) 2609-2617
8. Kellar K.E., Henrich P.M., Hollister R., Koenig S.H., Eck J., and Wei D. Magn. Reson. Med. 38 (1997) 712-716
9. Vexler V.S., Clement O., Schmitt-Willich H., and Brasch R.C. J. Magn. Reson. Im. 4 (1994) 381-388
10. Desser T.S., Rubin D.L., Muller H.H., Qing F., Khodor S., Zanazzi G., Young S.U., Ladd D.L., Wellons J.A., Kellar K.E., Toner J.L., and Snow R.A. J. Magn. Reson. Im. 4 (1994) 467-472
11. Lauffer R.B., Brady T.J., Brown III R.D., Baglin C., and Koenig S.H. Magn. Reson. Med. 3 (1986) 541-548
12. Aime S., Botta M., Fasano M., Crich S.G., and Terreno E. J. Biol. Inorg. Chem. 1 (1996) 312-319
13. Toth E., Connac F., Helm L., Adzamli K., and Merbach A.E. J. Biol. Inorg. Chem. 3 (1998) 606-613
14. Vaccaro M., Accardo A., Tesauro D., Mangiapia G., Löf D., Schillen K., Söderman O., Morelli G., and Paduano L. Langmuir 22 (2006) 6635-6643
15. Accardo A., Tesauro D., Roscigno P., Gianolio E., Paduano L., D'Errico G., Pedone C., and Morelli G. J. Am. Chem. Soc. 126 (2004) 3097-3107
16. André J.P., Toth E., Fisher H., Seeling A., Mäcke H.R., and Merbach A.E. Chem. Eur. J. 5 (1999) 2977-2983
17. Hovland R., Glogard C., Aasen A.J., and Klaveness J. Org. Biomol. Chem. 1 (2003) 644-647
18. Debouttière P.-J., Roux S., Vocanson F., Billotey C., Beuf O., Favre-Réguillon A., Pellet-Rostaing S., Lamartine R., Perriat P., and Tillement O. Adv. Funct. Mater. 16 (2006) 2330-2339
19. Dioury F., Sambou S., Guéné E., Sabatou M., Ferroud C., Guy A., and Port M. Tetrahedron 63 (2007) 204-214
20. Dioury F., Sylvestre I., Siaugue J.-M., Wintgens V., Ferroud C., Favre-Réguillon A., and Guy A. Eur. J. Org. Chem. (2004) 4424-4436
21. Siaugue J.-M., Segat-Dioury F., Sylvestre I., Favre-Réguillon A., Madic C., and Guy A. Tetrahedron 57 (2001) 4713-4718
22. Aime S., Botta M., Crich S.G., Giovenzana G.B., Jommi G., Pagliarin R., and Sisti M. J. Chem. Soc., Chem. Commun. (1995) 1885-1886
23. Won D.K., Garry E.K., Maton F., McMillan K., Muller N.R., and Sherry A.D. Inorg. Chem. 34 (1995) 2233-2243
24. Aime S., Gianolio E., Corpillo D., Cavallotti C., Palmisano G., Sisti M., Giovenzana G.B., and Pagliarin R. Helv. Chim. Acta 86 (2003) 615-632
25. Aime S., Botta M., Crich S.G., Giovenzana G.B., Jommi G., Pagliarin R., and Sisti M. Inorg. Chem. 36 (1997) 2992-3000
26. Richman J.E., and Atkins T.J. J. Am. Chem. Soc. 96 (1974) 2268-2270
27. Aime S., Botta M., frullano L., Geninatti Crich S., Giovenzana G.B., Pagliarin R., Palmisano G., and Sisti M. Chem. Eur. J. 5 (1999) 1253-1260
28. Aime S., Cavallotti C., Gianolio E., Giovenzana G.B., Palmisano G., and Sisti M. Org. Lett. 6 (2004) 1201-1204
29. Hovinen J., and Sillanpää R. Tetrahedron Lett. 46 (2005) 4387-4389
30. Baldo M.A., Chessa G., Marangoni G., and Pitteri B. Synthesis (1987) 720-723
31. 2); 67.25 (C); 127.2, 128.4, 130.1 (ArCH); 145.2 (ArC).
32. Tsunoda T., Yamamiya Y., and Itô S. Tetrahedron Lett. 34 (1993) 1639-1642
33. Defacqz N., Tran-Trieu V., Cordi A., and Marchand-Brynaert J. Tetrahedron Lett. 44 (2003) 9111-9114
34. General procedure: 2a-c (1 mmol), 7 (1 mmol) and tributylphosphine (3 mmol) were dissolved in dry THF (25 mL). DIAD (3 mmol) was added in four portions during 15 min, and the reaction was stirred at room temperature for 4 h. All volatiles were removed in vacuum, and the residue was purified by chromatography on silica gel (ethyl acetate/heptane: 1/1-100/0) to give a light yellow solid.
35. Nihei K.-I., Kato T.Y., Yamane T., Palma M.S., and Konno K.S. Synlett 7 (2001) 1167-1169
36. Watanabe Y., Shiozaki M., and Kamegai R. Carbohydr. Res. 335 (2001) 283-289
37. Li Q., Li S.-C., Li H., Cai M.-S., and Li Z.-J. Carbohydr. Res. 340 (2005) 1601-1604
38. Broxterman Q.B., Kaptein B., Kamphuis J., and Schoemaker H.E. J. Org. Chem. 57 (1992) 6286-6294
39. Pearson D.A., Blanchette M., Baker M.L., and Guindon C.A. Tetrahedron Lett. 30 (1989) 2739-2742
40. 2); 119.9, 121.5 (CH); 147.9, 149.0, 151.0 (C); 168.0, 172.3 (C{double bond, long}O). MS: ESI: 471.2 [M+H].