79236-92-3

Usage

Uses

Used in Medical Applications:
CYCLEN-GLYOXAL is used as a chelating agent for its ability to bind to metal ions and deliver them to specific biological targets, which can be beneficial in various medical treatments.
Used in Antimicrobial Applications:
CYCLEN-GLYOXAL is used as an antimicrobial agent due to its potential to combat microorganisms, offering a possible solution in the fight against infections.
Used in Environmental Chemistry:
CYCLEN-GLYOXAL is used as a heavy metal remover for its capacity to extract heavy metals from water sources, playing a crucial role in environmental protection and water purification processes.

InChI:InChI=1/C10H18N4/c1-2-12-7-8-14-4-3-13-6-5-11(1)9(12)10(13)14/h9-10H,1-8H2/t9-,10+

Upstream product

• 106-93-4 ethylene dibromide 
• 182922-75-4 perhydropyrazo<1,2-a:2',1'-c>diimidazole 
• 131543-46-9 Glyoxal 
• 107-15-3 ethylenediamine 
• 112-24-3 triethylentetramine 
• 5409-42-7 decahydropyrazino[2,3-b]pyrazine 
• 294-90-6 1,4,7,10-tetraazacyclododecan 
• 95-92-1 oxalic acid diethyl ester 
• 215540-27-5 3H,6H-2a,5,6,8a-octahydrotetraaza-acenaphthylene 
• 4405-13-4 glyoxal trimer dihydrate 
• 368864-05-5 octahydro-2a,4a,6a,8a-tetraazacyclopent[fg]acenaphthylene-1,2-dione 
• 107-06-2 1,2-dichloro-ethane 
• 10045-25-7 1,4,7,10-tetraazacyclododecane tetrahydrochloride 

Downstream Products

• 294-90-6 1,4,7,10-tetraazacyclododecan 
• 107-15-3 ethylenediamine 
• 1380646-70-7 C₃₉H₅₉N₅O₅ 
• 745782-84-7 N-[(4-vinylphenyl)methyl]-1,4,7,10-tetraazacyclotetradecane 
• 1308789-79-8 1,7-bis(4-bromobenzyl)-4,10-dipyrimidin-2-yl-1,4,7,10-tetraazacyclododecane 

Relevant academic research and scientific papers

Preparation method of cyclen and intermediate thereof

The invention discloses a preparation method of cyclen and an intermediate thereof, specifically a preparation method of a compound as shown in a formula 4. The method comprises the following step: in water, carrying out a reduction reaction as shown in the specification on a compound as shown in a formula 3 and hydrazine hydrate, wherein X is phosphoric acid or sulfuric acid, when X is phosphoric acid, n is 4/3, and when X is sulfuric acid, n is 2. The preparation method has the advantages of low cost, simple operation, easy purification of intermediates and products, high yield and purity, and suitableness for industrial production.

An octadentate bis(semicarbazone) macrocycle: A potential chelator for lead and bismuth radiopharmaceuticals

A variant of 1,4,7,10-tetraazacyclododecane (cyclen) bearing two semicarbazone pendant groups has been prepared. The octadentate ligand forms complexes with Bi3+ and Pb2+. X-ray crystallography showed that the neutral ligand provides an eight-coordinate environment for both metal ions and intermolecular hydrogen bond interactions have influenced the coordination environments of both complexes in the solid state. NMR spectroscopy revealed a fluxional environment for both complexes. The ligand was radiolabeled with the α-emitting radioactive isotope 213Bi3+, which is used in systemic targeted radiotherapy. The resulting complex was stable in serum for at least 90 min (two decay half-lives). The Pb2+ complex has reasonably fast kinetics of formation (t1/2 = 20 min) at 25 °C and pH 7.4. The Bi3+ and Pb2+ complexes show kinetic stability in 1.2 M HCl (half-lives of 214 min and 47 min, respectively). This is the first description of a macrocycle bearing semicarbazone pendant groups and its utility in coordinating main group metals, specifically those with radiotherapeutic potential.

Definition of the Labile Capping Bond Effect in Lanthanide Complexes

Two macrocyclic ligands containing a cyclen unit, a methyl group, a picolinate arm, and two acetate pendant arms attached to two nitrogen atoms of the macrocycle either in trans (1,7-H3Medo2 ampa = 2,2′-(7-((6-carboxypyridin-2-yl)methyl)-10-met

Incorporation of Cobalt-Cyclen Complexes into Templated Nanogels Results in Enhanced Activity

Recent advances in nanomaterials have identified nanogels as an excellent matrix for novel biomimetic catalysts using the molecular imprinting approach. Polymerisable Co-cyclen complexes with phosphonate and carbonate templates have been prepared, fully characterised and used to obtain nanogels that show high activity and turnover with low catalytic load, compared to the free complex, in the hydrolysis of 4-nitrophenyl phosphate, a nerve agent simulant. This work demonstrates that the chemical structure of the template has an impact on the coordination geometry and oxidation state of the metal centre in the polymerisable complex resulting in very significant changes in the catalytic properties of the polymeric matrix. Both pseudo-octahedral cobalt(III) and trigonal-bipyramidal cobalt(II) structures have been used for the synthesis of imprinted nanogels, and the catalytic data demonstrate that: i) the imprinted nanogels can be used in 15 % load and show turnover; ii) the structural differences in the polymeric matrices resulting from the imprinting approach with different templates are responsible for the molecular recognition capabilities and the catalytic activity. Nanogel P1, imprinted with the carbonate template, shows >50 % higher catalytic activity than P2 imprinted with the phosphonate.

A high-purity torus cane rather method for the preparation of

The invention provides a preparation method of high-purity cyclen. The method comprises the following preparation paths. Cyclen obtained by the method of the invention has high purity. At the same time, the method greatly reduces the energy consumption and the power cost, and thereby reducing the raw material cost; the method greatly improves the reaction rate, reduces the catalyst amount and the reaction temperature, thereby shortening the consuming time of the process, and reducing the process cost; and the method greatly reduces the acid amount consumption, and thereby greatly reducing the equipment loss. The preparation method improves the production efficiency, and enables the product quality to reach more than 99.8%; hydrazine hydrate is used for replacing diethylenetriamine for a hydrolysis reaction, so the process is suitable for industrialized production. The method of the invention is environmentally friendly, is cost-saving, and is suitable for environment-friendly industrialization.

BIFUNCTIONAL do2pa DERIVATIVES, CHELATES WITH METALLIC CATIONS AND USE THEREOF

The present invention relates to chelates resulting from the complexation of bifunctional do2pa derivatives ligands of formula (I), wherein the substituents R1, R1', R2, R2', R3, R3', Lsup

Copper(II) and gallium(III) complexes of trans -Bis(2-hydroxybenzyl) cyclen derivatives: Absence of a cross-bridge proves surprisingly more favorable

Two cyclen (1,4,7,10-tetraazacyclododecane) derivatives bearing trans-bis(2-hydroxybenzyl) arms, the 1,7-(2-hydroxybenzyl)-1,4,7,10- tetraazacyclododecane (H2do2ph) and its cross-bridged counterpart (H2cb-do2ph), have been synthesized, aiming toward the possible use of their copper(II) and gallium(III) complexes in nuclear medicine. The protonation of both compounds was studied in aqueous solution as well as their complexes with Cu2+ and Ga3+ cations. The complexes of both ligands with Ca2+ and Zn2+ metal ions were also studied due to the abundance of these cations in biological media. In mild conditions the complexes of Ca2+ and Ga3+ with H 2cb-do2ph did not form. The behavior of the two ligands and their complexes was compared by the values of the equilibrium constants, the data of varied spectroscopic techniques, the values of redox potentials of their copper(II) complexes, and the resistance of the complexes to acid dissociation. It was expected that, as found for related pairs of cyclen and cyclam (1,4,8,11-tetraazacyclotetradecane) derivatives, the cross-bridged macrocyclic derivative could be an excellent ligand for the complexation of copper(II). Additionally, the N-2-hydroxybenzyl groups were chosen due to their known ability to coordinate the gallium(III) cation. Due to the small size of the latter cation and its particular propensity to form hexacoordinate complexes, it was also expected that there would be a good ability of both ligands for the uptake of Ga3+. Surprisingly, the results revealed that the cyclen derivative H2do2ph is the best ligand for the coordination of Cu 2+ and Ga3+ cations, not only from their thermodynamic stability as expected but also from their kinetic inertness, when compared with its cross-bridged counterpart.

Picolinate-containing macrocyclic Mn2+ complexes as potential MRI contrast agents

We report the synthesis of the ligand Hnompa (6-((1,4,7-triazacyclononan-1- yl)methyl)picolinic acid) and a detailed characterization of the Mn2+ complexes formed by this ligand and the related ligands Hdompa (6-((1,4,7,10-tetraazacyclododecan-1-yl)methyl)picolinic acid) and Htempa (6-((1,4,8,11-tetraazacyclotetradecan-1-yl)methyl)picolinic acid). These ligands form thermodynamically stable complexes in aqueous solution with stability constants of logKMnL = 10.28(1) (nompa), 14.48(1) (dompa), and 12.53(1) (tempa). A detailed study of the dissociation kinetics of these Mn 2+ complexes indicates that the decomplexation reaction at about neutral pH occurs mainly following a spontaneous dissociation mechanism. The X-ray structure of [Mn2(nompa)2(H2O) 2](ClO4)2 shows that the Mn2+ ion is seven-coordinate in the solid state, being directly bound to five donor atoms of the ligand, the oxygen atom of a coordinated water molecule and an oxygen atom of a neighboring nompa- ligand acting as a bridging bidentate carboxylate group (μ-η1-carboxylate). Nuclear magnetic relaxation dispersion (1H NMRD) profiles and 17O NMR chemical shifts and transverse relaxation rates of aqueous solutions of [Mn(nompa)]+ indicate that the Mn2+ ion is six-coordinate in solution by the pentadentate ligand and one inner-sphere water molecule. The analysis of the 1H NMRD and 17O NMR data provides a very high water exchange rate of the inner-sphere water molecule (kex 298 = 2.8 × 109 s-1) and an unusually high value of the 17O hyperfine coupling constant of the coordinated water molecule (AO/h = 73.3 ± 0.6 rad s-1). DFT calculations performed on the [Mn(nompa)(H2O)]+· 2H2O system (TPSSh model) provide a AO/h value in excellent agreement with the one obtained experimentally.

A novel synthesis of 1,4,7,10-tetraazacyclododecane by the tandem reaction of a vinylsulfonium salt

1,4,7,10-Tetraazacyclododecane was synthesized through 4 steps by using easily available diphenylsulfonium triflate as a key annulation reagent. The reaction condition was very mild and the yield was high. After oxidation and hydrolysis, 1,4,7,10-Tetraazacyclododecane, which had been proven to be the pivotal precursor for a wide range of MRI contrast reagents, was produced in an overall yield of 31%.

Heteroditopic receptor based on crown ether and cyclen units for the recognition of zwitterionic amino acids

The molecular recognition of five targeted amino acids differing in the nature of the side (R)- group and in the size of the aliphatic chain, glycine (Hgly), phenylalanine (Hphe), glutamic acid (Hglu-), 4-aminobutyric acid (Hgaba), and 6-aminohexanoic acid (Heahx), has been studied with a new heteroditopic receptor based in two distinct macrocycles, a cyclen and a crown ether moiety. The bismacrocycle L was synthesized via the bis-aminal route allowing to obtain the designed compound in gram scale and in good yield. Protonation constants of L and its binding constants with amino acids were determined by potentiometry in H2O/MeOH (1:1 v/v) solutions at 298.2 K and I=0.10 mol dm-3 in NMe4NO3. Stronger binding ability of the HnLn+ receptor for α-amino acids, Hgly and Hphen, than for the other studied substrates were found. Structural data derived from NMR studies showed that the binding of α-amino acids result from the cooperative participation of hydrogen bonds between the carboxylate group of amino acids and the polyammonium sites of cyclen, and the ion-dipole interactions between the ammonium group of the amino acids and the oxygen atoms of the crown ether.