Abstract
A new bifunctional cyclen-based ligand, 3-[hydroxy({4,7,10-tris[(tert-butoxycarbonyl)methyl]-1,4,7,10-tetraazacyclododecan-1-yl}methyl)phosphoryl]propanoic acid, was synthe-sized by alkylation of tri-tert-butyl 1,4,7,10-tetraazacyclododecane-1,4,7-triacetate (t-Bu3DO3A) by ethyl 3-{ethoxy[(mesyloxy)methyl]phosphoryl}propanoate [MsOCH2P(O)(OEt)CH2CH2CO2Et]. The ethyl carboxylate group in the side chain was selectively deprotected to obtain the esterified bifunctional ligand. More efficient syntheses of some phosphinopropanoic acid derivatives were devised and the phosphorus alkylation reagent was prepared starting from hypophosphorus acid or its salt.
Key words
macrocycles - MRI contrast agents - phosphinate ligands - phosphorus - radiopharmaceuticals
References
1a
Caravan P.
Chem. Soc. Rev.
2006,
35:
512
1b
Aime S.
Botta M.
Terreno E.
Adv. Inorg. Chem.
2005,
57:
173
1c
Topics in Current Chemistry
Vol. 221:
Springer;
Heidelberg:
2002.
1d
The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging
Merbach AE.
Tóth É.
Wiley;
Chichester:
2001.
1e
Caravan P.
Ellison JJ.
McMurry TJ.
Lauffer RB.
Chem. Rev.
1999,
99:
2293
2a
Li WP.
Meyer LA.
Anderson CJ.
Top. Curr. Chem.
2005,
252:
179
2b
Liu S.
Chem. Soc. Rev.
2004,
33:
445
2c
Handbook of Radiopharmaceuticals. Radiochemistry and Applications
Welch MJ.
Redvanly CS.
Wiley;
Chichester:
2003.
2d
Liu S.
Edwards DS.
Bioconjugate Chem.
2001,
12:
7
3
Denat F.
Brandés S.
Guilard R.
Synlett
2000,
561
4
Rudovsk J.
Cígler P.
Kotek J.
Hermann P.
Vojtíek P.
Luke I.
Peters JA.
Elst LV.
Muller RN.
Chem. Eur. J.
2005,
11:
2373
5
Rudovsk J.
Kotek J.
Hermann P.
Luke I.
Mainero V.
Aime S.
Org. Biomol. Chem.
2005,
3:
112
6
Lebduková P.
Hermann P.
Helm L.
Tóth É.
Kotek J.
Binnemans K.
Rudovsk J.
Luke I.
Merbach AE.
Dalton Trans.
2007,
493
7
Rudovsk J.
Botta M.
Hermann P.
Koridze A.
Aime S.
Dalton Trans.
2006,
2323
8
Táborsk P.
Lubal P.
Havel J.
Kotek J.
Hermann P.
Luke I.
Collect. Czech. Chem. Commun.
2005,
70:
1909
9
Försterová M.
Svobodová I.
Lubal P.
Táborsk P.
Kotek J.
Hermann P.
Luke I.
Dalton Trans.
2007,
535
10a
Rudovsk J.
Botta M.
Hermann P.
Hardcastle KI.
Luke I.
Aime S.
Bioconjugate Chem.
2006,
17:
975
10b
Rudovsk J.
Hermann P.
Botta M.
Aime S.
Luke I.
Chem. Commun.
2005,
2390
11 Försterová, M.; Petřík, M.; Lázničková, A.; Lázníček, M.; Hermann, P.; Luke, I.; Melichar, F. Appl. Radiat. Isotop. 2008, submitted.
12a
Broan CJ.
Cole E.
Jankowski KJ.
Parker D.
Pulukkody K.
Boyce BA.
Beeley NRA.
Millar K.
Millican AT.
Synthesis
1992,
63
12b
Li X.
Zhang S.
Zhao P.
Kovacs Z.
Sherry AD.
Inorg. Chem.
2001,
40:
6572
12c
Chavez MR.
Zhao P.
Kovacs Z.
Sherry AD.
Lett. Org. Chem.
2004,
1:
194
13a
Fitch SJ.
J. Am. Chem. Soc.
1964,
86:
61
13b
Pinnich HW.
Reynolds MA.
Synth. Commun.
1979,
9:
535
13c
Stawinski J.
Thelin M.
Westman E.
Zain R.
J. Org. Chem.
1990,
55:
3505
14
Maier L.
Helv. Chim. Acta
1973,
56:
489
15
Montchamp J.-L.
J. Organomet. Chem.
2005,
690:
2388
16
Deprele S.
Montchamp J.-L.
J. Organomet. Chem.
2002,
643-644:
154
17
Wróblewski AE.
Verkade JG.
J. Am. Chem. Soc.
1996,
118:
10168
18a
Issleib K.
Mögelin W.
Balszuweit A.
Z. Anorg. Allg. Chem.
1985,
530:
16
18b
Boyd EA.
Corless M.
James K.
Regan AC.
Tetrahedron Lett.
1990,
31:
2933
18c
Boyd EA.
Regan AC.
James K.
Tetrahedron Lett.
1994,
35:
4223
19
Kaestle KL.
Anwer MK.
Audhya TK.
Goldstein G.
Tetrahedron Lett.
1991,
32:
327
20
Kafarski P.
Lejczak B. In
Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity
Kukhar VP.
Hudson HR.
Wiley;
Chichester:
2000.
p.173-203
21
Dadabhoy A.
Faulkner S.
Sammes PG.
J. Chem. Soc., Perkin Trans. 2
2002,
348
22
Perrin DD.
Armarego WLF.
Purification of Laboratory Chemicals
4th. ed.:
Pergamon Press;
Oxford:
1988.
