174912-95-9

Usage

Chemical class

Triazacyclononane ligands

Structure

Nine-membered ring with three nitrogen atoms and one benzyl group attached to one of the nitrogen atoms

Application

Widely used as a ligand in coordination chemistry

Complex formation

Can complex with various metal ions to form stable coordination complexes

Potential applications

a. Catalysis
b. Development of new materials
c. Pharmaceutical drugs

Investigated properties

a. Antibacterial activities
b. Antifungal activities

Interest areas

Biomedical and agricultural applications

Upstream product

• 56234-52-7 1,8-bis(p-toluenesulfonyloxy)-3,6-bis(p-toluenesulfonyl)-3,6-diazaoctane 
• 100-39-0 benzyl bromide 
• 67705-38-8 tacnoa 
• 4730-54-5 1,4,7-triazacyclononane 
• 100-46-9 benzylamine 
• 190257-84-2 1-benzyl-4,7-di(p-toluenesulfonyl)-1,4,7-triazacyclononane 
• 112498-58-5 4-benzyl-1,4,7-triazacyclononane-1-carbaldehyde 

Downstream Products

• 186499-21-8 1-benzyl-4,7-bis(2-hydroxy-2-methylpropyl)-1,4,7-triazacyclononane 
• 1360542-38-6 C₄₃H₆₅N₃O₂ 
• 1397275-78-3 C₄₁H₇₁N₁₂O₁₆P₃ 
• 1357009-14-3 di-tert-butyl 2,2′-(7-benzyl-1,4,7-triazonane-1,4-diyl)diacetate 
• 174137-97-4 1,4-bis(tert-butoxycarbonylmethyl)-1,4,7-triazacyclononane 

Relevant academic research and scientific papers

A Class of FeIII Macrocyclic Complexes with Alcohol Donor Groups as Effective T1 MRI Contrast Agents

Early studies suggested that FeIII complexes cannot compete with GdIII complexes as T1 MRI contrast agents. Now it is shown that one member of a class of high-spin macrocyclic FeIII complexes produces more intense contrast in mice kidneys and liver at 30 minutes post-injection than does a commercially used GdIII agent and also produces similar T1 relaxivity in serum phantoms at 4.7 T and 37 °C. Comparison of four different FeIII macrocyclic complexes elucidates the factors that contribute to relaxivity in vivo including solution speciation. Variable-temperature 17O NMR studies suggest that none of the complexes has a single, integral inner-sphere water that exchanges rapidly on the NMR timescale. MRI studies in mice show large in vivo differences of three of the FeIII complexes that correspond, in part, to their r1 relaxivity in phantoms. Changes in overall charge of the complex modulate contrast enhancement, especially of the kidneys.

COMPOUNDS FOR USE AS IRON (III) MRI CONTRAST AGENTS CONTAINING ANIONIC PENDENTS AND ANCILLARY GROUPS

Macrocyclic complexes and macrocyclic compounds. The macrocyclic complexes or macrocyclic compounds have a TACN moiety with one or more amine group(s) or a O- or S- substituted TACN moiety. The macrocyclic complexes have a high-spin Fe(III) atom coordinated to the TACN moiety. The macrocyclic complexes can be used in imaging methods.

COMPOUNDS FOR USE AS IRON(III) MRI CONTRAST AGENTS

Provided are macrocyclic compounds and compounds with two or more macrocyclic groups, iron coordinated macrocyclic compounds, and iron coordinated compounds with two or more macrocyclic groups. The iron is high-spin iron(III). The iron coordinated compoun

A pair of highly biotolerated diamagnetic and paramagnetic iron(II) complexes displaying electroneutrality

A pair of structurally analogous macrocyclic iron(ii) complexes with a magnetic off-on relationship is reported that exhibit electroneutrality at neutral pH and high stability in physiological media. This has been achieved by external charge compensation using nicotinate pendent arms. No contact toxicity was observed for cells up to 4 mM for the low-spin and 2 mM for the high-spin complex. These results are a necessary precursor to the future design of turn-on probes with elevated biotolerance.

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

A short and efficient synthesis of mono-substituted 1,4,7-Triazacyclononanes

A convenient synthesis of 1,4,7-Triazacyclononane (tacn) derivatives substituted with a single pendant donor group is described. Monosubstituted tacns with a hydroxylalkyl, an aminoalkyl, or a benzyl group are synthesized via efficient cyclization of inex

Selective derivatisation of aza macrocycles

A range of selectively functionalised compounds derived from 1,4,7-triazacyclononane ([9]aneN3), including 4,7-bis(2-hydroxy-2-methylpropyl)-1,4,7-triazacyclononane-1-carbaldehyde (H2L1), 1-benzyl-4,7-bis(2-hydroxy-2-methylpropyl)-1,4,7-triazacyclononane (H2L2) and 1,4-bis(2-hydroxy-2-methylpropyl)-1,4,7-triazacyclononane (H2L3), has been prepared. The structure of H2L3·CHCl3 shows a disordered macrocyclic ring with the major conformer refining to a site occupancy of 0.663(8), and both disordered rings adopting a [333] conformation. The pendant alcohol arms were not disordered and were found to be hydrogen bonded to a CHCl3 solvate molecule with H ... O(1) and H ... O(4) distances of 1.73 and 1.81 A respectively. The structure of Na[Cu(H2L1)(NCMe)][BF4]2[NO 3] shows the copper(II) centre in the [Cu(H2L1)(NCMe)]2+ cation bound to two amine donors and two alcohol donors of H2L1 and to a MeCN molecule. The Cu-N bond lengths lie in the range 1.984(3)-2.015(3) A. Both alcohol donors are protonated, with one short Cu-O(16) bond of 1.963(3) A and one long Cu-O(21) bond of 2.252(3) A. There is also a sixth longer-range interaction of the copper(II) centre with the amide N [N(1)] of H2L1 at a distance of 2.611(5) A, confirmed by the loss of planarity of the C(2)-C(9)-N(1)-C(10)-O(11)-H(10) amide fragment to give a dihedral angle between the planes defined by C(2)-C(9)-N(1) and N(1)-C(10)-O(11)-H(10) of 27.1(4)°. The structure is completed by interaction of O(11) with a Na+ ion which itself bridges to BF4- counter anions leading to a central infinite core of [Na(BF4)2]- aggregates onto which are attached the [Cu(H2L1)(NCMe)]2+ cations. The complex [Cu(H2L2)(OH2)][NO3]2 shows the six-co-ordinate copper(II) centre bound to the three amine and two alcohol donors of H2L2 and to one water molecule. There are four short bonds [to N(7), N(4), O(40) and O(1)] in the range 1.961(5)-2.073(6) A and two longer bonds to N(1) and O(70) at 2.308(5) and 2.313(5) A respectively. The H atoms of the water molecule [O(1)] and one of the pendant arms [O(40)] also make hydrogen-bonding contacts with the nitrate counter ions.

Asymmetric functionalisation of aza macrocycles. Syntheses, crystal structures and electrochemistry of [Ni(Bz[9]aneN3)2] [PF6]2 and [Pd(Bz[9]aneN3)2] [PF6]2·2MeCN (Bz[

1-Benzyl-1,4,7-triazacyclononane (Bz[9]aneN3) has been prepared and its co-ordination chemistry with NiII and PdII investigated. The crystal structure of the complex [Ni(Bz[9]aneN3)2][PF6]

Stacked Amido Macrocyclic Complexes: Synthesis and Single Crystal X-Ray Structure of Na(BF4)2(NO3)

The synthesis of bi-functional derivatives of aneN3 is described; the structure of Na(BF4)2(NO3) shows a central - core with the O-donor of the amide moiety of successive 2+ cations bound to Na+ to give a stacked str