174137-97-4

Usage

Uses

Used in Chemical Synthesis:
1,4-bis(tert-butoxycarbonylmethyl)-1,4,7-triazacyclononane is used as a reactive intermediate for the synthesis of high-spin iron(II) and cobalt(II) N-methylated N-methylpicolyl cyclen complexes. These complexes are valuable as paraSHIFT agents, which are utilized in nuclear magnetic resonance (NMR) spectroscopy to enhance the resolution of complex mixtures by providing large temperature-dependent shifts.
Used in Nuclear Magnetic Resonance (NMR) Spectroscopy:
In the field of NMR spectroscopy, 1,4-bis(tert-butoxycarbonylmethyl)-1,4,7-triazacyclononane is used as a precursor for the development of paraSHIFT agents. These agents are essential for improving the spectral resolution of complex mixtures, allowing for more accurate identification and characterization of compounds in various research and industrial applications.

Upstream product

• 5292-43-3 bromoacetic acid tert-butyl ester 
• 4730-54-5 1,4,7-triazacyclononane 
• 67705-38-8 tacnoa 
• 174912-95-9 1-benzyl-[1,4,7]-triazacyclononane 
• 1357009-14-3 di-tert-butyl 2,2′-(7-benzyl-1,4,7-triazonane-1,4-diyl)diacetate 
• 1092370-25-6 C₂₅H₄₁N₃O₆S 
• 174138-01-3 1,4-di-tert-butyl 1,4,7-triazonane-1,4-dicarboxylate 
• 174138-02-4 1-Cbz-1,4,7-triazacyclononane 

Downstream Products

• 1016237-70-9 (4-[2-(benzyl-tert-butoxycarbonylmethyl-amino)ethyl]-7-tert-butoxycarbonyl-methyl-[1,4,7]triazonan-1-yl)acetic acid tert-butyl ester 
• 1016237-79-8 t-butyl (4-tert-butoxycarbonylmethyl-7-{2-[tert-butoxycarbonylmethyl-(4-nitro-benzyl)-amino]ethyl}-[1,4,7]triazonan-1-yl)acetate 
• 1041706-11-9 tert-butyl {4-[2-(bis-benzyloxycarbonylmethyl-amino)ethyl]-7-tert-butoxycarbonylmethyl [1,4,7]triazonan-1-yl}acetate 
• 1092370-30-3 C₃₀H₄₈N₄O₈ 
• 1092370-22-3 C₃₂H₅₁N₃O₈ 
• 1262392-67-5 C₂₇H₄₄N₄O₅ 
• 1261060-08-5 C₄₁H₆₃N₃O₆ 
• 1325166-12-8 C₄₇H₇₅N₃O₆ 
• 1353022-78-2 tert-butyl 2-[benzyl(1-{4,7-bis[2-(tert-butoxy)-2-oxoethyl]-1,4,7-triazonan-1-yl}-3-(4-nitrophenyl)propan-2-yl)amino] acetate 
• 1161415-28-6 2-{4,7-bis-tert-butoxycarbonylmethyl-[1,4,7] triazocyclononan-1-yl}acetic acid 

Relevant academic research and scientific papers

A CoII complex for19F MRI-based detection of reactive oxygen species

A fluorinated, air-stable cobalt(ii) complex serves as a turn-on19F magnetic resonance imaging (MRI) tracer for reactive oxygen species including H2O2. Upon oxidation with H2O2, the complex converts from paramagnetic high spin CoII to diamagnetic low spin CoIII resulting in a chemical shift change and enhancement in19F NMR signal. Further, the oxidation can be reversed in the presence of reductant Na2S2O4. The turn-on response is demonstrated by19F MRI, characterized by a ～2-3 fold enhancement in signal.

A practical route for the preparation of 1,4,7-triazacyclononanyl diacetates with a hydroxypyridinonate pendant arm

The preparation of triazamacrocyclic hydroxypyridinonate (HOPO-TACN) derivatives as potential chelators for metals in biomedical applications was reported. The synthesis is based on a convergent synthetic approach, in which the key intermediate di-tert-butyl-2,2′-(1,4,7-triazonane-1,4-diyl) diacetate was coupled with a hydroxypyridinonate pendant arm. The method is suitable for rapid syntheses of metal chelator HOPO-TACNs of biomedical interest.

Gd3+-based magnetic resonance imaging contrast agent responsive to Zn2+

We report the heteroditopic ligand H5L, which contains a DO3A unit for Gd3+ complexation connected to an NO2A moiety through a N-propylacetamide linker. The synthesis of the ligand followed a convergent route that involved the prepar

Stable aluminium fluoride chelates with triazacyclononane derivatives proved by X-ray crystallography and 18F-labeling study

A single crystal structure of an aluminium-fluoride complex of a model compound (NODA-benzyl) was studied to understand the co-ordination chemistry. Series of ligands with an extra carboxylic acid linker for biomolecule conjugation were studied for improv

Efficient synthesis and evaluation of bimodal ligand NETA

The efficient and short synthetic route to the structurally novel bimodal ligand NETA for antibody-targeted radiation therapy (radioimmunotherapy, RIT) of cancer was developed. The structure of NETA was determined by X-ray crystallography. The arsenazo-ba

NODAPA-OH and NODAPA-(NCS)n: Synthesis, 68Ga-radiolabelling and in vitro characterisation of novel versatile bifunctional chelators for molecular imaging

This report concerns synthesis, 68Ga-radiolabelling and stability data of 1,4,7-triazacyclononane-1,4-diacetic acid-7-p-isothio-cyanatophenyl-acetic acid (NODAPA-NCS), 1,4,7-triazacyclononane-1-acetic acid-4,7-di-p-isothiocyanatophenyl-acetic acid (NODAPA-(NCS)2) and 1,4,7-triazacyclononane-1,4-diacetic acid-7-p-hydroxyphenyl-acetic acid (NODAPA-OH), versatile bifunctional chelators with potential for molecular imaging. Protein binding and exemplified conjugation are also reported.

Synthesis and characterization of 1,4,7-triazacyclononane derivatives with methylphosphinate and acetate side chains for monitoring free MgII by31P and1H NMR spectroscopy

A series of 1,4,7-triazacyclononane-based ligands containing one, two, or three methylphosphinate (MP) side chains has been prepared. The macrocycle with three methylpbosphinates, NOTMP, appeared to be a very promising ligand for monitoring MgII in biological samples by 31P NMR spectroscopy. The 31P resonances of the free ligand and the MgII complex were well resolved, in slow exchange, and well downfield of typical tissue phosphate and phosphate ester metabolite resonances. The Kd value of the Mg(NOTMP) complex was 0.35 mM at physiological pH and temperature, a value which is optimal for accurate assessment of free MgII in cells and blood plasma. The latter was confirmed experimentally. Furthermore, the selectivity of NOTMP for MgII over CaII exceeded 2 orders of magnitude. The Kd values of the MgII complexes were sensitive to pH and temperature. The pH effects could be easily predicted from potentiometric pH titration data. Examination of the MgII ligand equilibria by 31P NMR over a wide temperature range provided complexation enthalpies and entropies. It was shown that the smaller Kd values at higher temperatures were largely due to a temperature effect on the highest ligand protonation constant. Only a small endothermic complexation enthalpy contributed to this phenomenon.

A General Synthesis of Mono- and Disubstituted 1,4,7-Triazacyclononanes

1,4,7-Triazacyclononane reacts selectively with 2-(t-butoxycarbonyloxyimino)- and 2-(benzyloxycarbonyloxyimino)-2-phenylacetonitrile to give 1,4-diprotected derivatives which could be converted to mono and disubstituted triazacyclononanes.