1.4.7.10- tetraazacyclododecane. synthesis

Macke recently introduced a monoreactive DOTA prochelator (4,7,10-tricarboxymethyl-tert-butyl ester A, A, A", A "-tetraazacyclododecane-1 -acetate), which was coupled to Tyr3—Lys5 (BOQ-octreotide via solid-phase peptide synthesis. A one-step deprotection reaction generated the bioactive compound DOTATOC in about 65% yield.142 The 90Y and 177Lu DOTATOC complexes have shown promise for the treatment of neuroendocrine tumors in early clinical trials.143,444... 

Renn, O., and Meares, C.F. (1992) Large scale synthesis of the bifunctional chelating agent 2-p-nitroben-zyl-l,4,7,10-tetraazacyclododecane-N,N, N"N" -tetraacetic acid and the determination of its enantiomeric purity by chiral chromatography. Bioconjugate Chem. 3, 563-569. 

Figure 4.5 Structure of Nd(6)CH3CN(CF3S03)2 [7]. (Redrawn fromR Wei, T. Jin and G Xu, Synthesis and crystal structure of neodymium complex of 1-methyl-1,4,7,10-tetraazacyclododecane, Acra Chimica Sinica, 50, 883, 1992.)...

Borbas, K.E. and Bruce, J.I. (2006) Synthesis of asymmetrically substituted 1,4,7,10-tetraazacyclododecanes for the triggered near infrared emission from lanthanide complexes. Chemical Communications, 4596. 

One-stage synthesis of medium-sized unsaturated lactones, thiolactones, and lactams of fi-configuration using the Bellu-Claisen rearrangement 04AG(E)3516. Syntheses of 1,4,7,10-tetraazacyclododecane and its derivatives 03MI91. 

The macrocycle l,4,7,10-tetraazacyclododecane-N,N, N",N" -tetraacetic acid (DOTA) is known to form stable complexes with lanthanides. A steroid conjugate (Fig. 8.16) was prepared via coupling of 6a-amino-17p-estradiol with a C functionalized DOTA derivative, namely, p-thiocyanatobenzyl DOTA, as a BFCA. The synthesis of 6a-amino-17p-estradiol was carried out by a four step reaction sequence. The intermediate and target compounds were characterized using high resolution H-NMR spectroscopy. 

Synthesis of 2-(p-nitrobenzyl)-1 A7J0-tetraazacyclododecane-N,N, N",N "-tetraacetic acid (McMurry et al. 1992)... 

Synthesis of DOTA-based bifunctional prochelator (4,7,10-tricarboxymethyl-feit-butyl ester 1,4,7,10-tetraazacyclododecane-l-acetate) (Heppeler et al. 1999a)... 

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