31250-18-7

Usage

Uses

Used in Medical Imaging:
5,6-Benzo-4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacos-5-ene is used as a model ligand for metal-ligand complex formation studies. It is particularly useful in predicting ligand coordination with metal ions such as Europium (Eu) and Gadolinium (Gd) using magnetic resonance imaging (MRI) techniques. This application is crucial for enhancing the contrast and diagnostic capabilities of MRI in various medical applications.
Used in Coordination Chemistry Research:
In the field of coordination chemistry, 5,6-Benzo-4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacos-5-ene is used to study the coordination environment, as well as the redox and electronic properties of its Ytterbium (YbII) complexes. This research is essential for understanding the fundamental interactions between metal ions and ligands, which can lead to the development of new materials and applications in various industries.
Overall, 5,6-Benzo-4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacos-5-ene is a versatile compound with potential applications in medical imaging and coordination chemistry research. Its unique molecular structure and properties make it a valuable tool for studying metal-ligand interactions and developing new materials and techniques for various applications.

InChI:InChI=1/C22H36N2O6/c1-2-4-22-21(3-1)29-15-9-23-5-11-25-17-19-27-13-7-24(10-16-30-22)8-14-28-20-18-26-12-6-23/h1-4H,5-20H2

Upstream product

• 80679-40-9 C₂₂H₃₆N₂O₆*Ca⁽²⁺⁾ 
• 36839-55-1 1,2-bis-(2-iodoethoxy)ethane 
• 31250-16-5 [2-(2-chloro-2-oxoethoxy)phenoxy]acetyl chloride 
• 120-80-9 benzene-1,2-diol 
• 31250-17-6 5,6-benzo-4,7,13,16,20,23-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane-2,9-dione 
• 5411-14-3 2-[2-(2-hydroxy-2-oxoethoxy)phenoxy]acetic acid 
• 167638-32-6 di-tert-butyl 2,2'-(1,2-phenylenebis(oxy))diacetate 
• 110431-62-4 1,2-bis-(2-iodoethoxy)benzene 
• 23978-55-4 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane 
• 95029-33-7 Ag⁽¹⁺⁾*C₂₂H₃₆N₂O₆ = Ag(C₂₂H₃₆N₂O₆)⁽¹⁺⁾ 
• 31364-42-8 kryptofix 221 
• 95048-51-4 Pb⁽²⁺⁾*C₂₂H₃₆N₂O₆ = Pb(C₂₂H₃₆N₂O₆)⁽²⁺⁾ 
• 23978-09-8 [2.2.2]cryptande 
• 72814-05-2 N,N-dimethyl-1,7,10,16-tetraoxa-4,13-diaza-(16)orthocyclophan 

Relevant academic research and scientific papers

Alkaline Earth Cryptates: Dynamics and Stabilities in Different Solvents

The stability constants and rates of formation and dissociation of alkaline earth cryptates with (2,1,1), (2,2,1), (2,2,2), (2B,2,2), and (2B,2B,2) have been measured in several solvents.The stability constants, Ks, are considerably larger and display higher selectivity than those of the monocyclic crown and diaza crown ethers and anionic ionophores.Values of Ks vary by over 10 orders of magnitude in the different solvents, increasing in the order Me2SO d).The rates show no correlation with solvent exchange rates, and are sensitive to cation size, cation-solvent interactions, and ligand flexibility.In strongly solvating media such as Me2SO, rates are up to 106 lower than predicted by a simple Id mechanism.The results suggest that the complexation reaction involves essentially stepwise replacement of solvent by ligand donor atoms, but that even for relatively flexible macrocyclic ligands compensation for loss in solvation by ligand binding energy in the transition state is not complete.

Synthesis and Evaluation of Bifunctional [2.2.2]-Cryptands for Nuclear Medicine Applications

For the first time, synthesis of bifunctional [2.2.2]-cryptands (CRYPT) and demonstration of radiolabeling with lead(II) (Pb2+) isotopes are disclosed herein. The synthesis is convenient and high-yielding and gives access to three distinct bifunctional handles (azide (-N3), isothiocyanate (-NCS), and tetrazine (-Tz)) that can enable the construction of radioimmunoconjugates for targeted and pretargeted therapy. Proof-of-principle CRYPT radiolabeling was successful with lead-203 ([203Pb]Pb2+) and demonstrated complexation efficiency superior to that of DOTA (1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid) and efficiency comparable to that of the current industry standard TCMC (1,4,7,10-tetraaza-1,4,7,10-tetra-(2-carbamoylmethyl)-cyclododecane). In vitro human serum stability assays demonstrated excellent [203Pb]Pb-CRYPT stability over 72 h (91.7 ± 0.56%; n = 3). [203Pb]Pb-CRYPT-radioimmunoconjugates were synthesized from the corresponding CRYPT-immunoconjugate or by conjugating [203Pb]Pb-Tz-CRYPT to transcyclooctene modified trastuzumab (TCO-trastuzumab) via the inverse electron-demand Diels-Alder (IEEDA) reaction. This investigation reveals the potential for CRYPT ligands to become new industry standards for therapeutic and diagnostic radiometals in radiopharmaceutical elaboration.

Synthesis of azacrown ethers and benzocryptands by macrocyclization of podands at high concentrations of reactants

The reactions of 1,2-bis(2-Y-ethoxy)benzenes, N,N-bis(2-Y-ethyl)-N- phenylamines, or 2,6-bis(Y-methyl)pyridines (Y = I, Br, or OTs) with α,ω-polyoxaalkanediamines or diazacrown ethers in the presence or absence of alkali carbonates in a concentrated acetonitrile solution of the reactants afforded the corresponding azacrown ethers or cryptands in high yields.

Solvent Dependence of Kinetics and Equilibria of Thallium(I) Cryptates in relation to the Free Energies of Solvation of Thallium(I)

Stability constant and dissociation rate constants of thallium(I) cryptates have been measured in several solvents at 25 deg C.The Tl+ cryptates are more stable and less sensitive to ligand cavity size than the corresponding complexes of the al

Synthesis of Simple Cryptands under High Pressure

Simple N,N'-dimethyl diaza-crown ethers react with bis(2-iodoethyl)-ether (2a) and 1,2-bis(2-iodoethoxy)ethane (2b) under high pressure (10 kbar) to give bis-quaternary salts which are demethylated in good yield by triphenylphosphine in boiling dimethylformamide yielding simple cryptands.

Kinetics of Ligand-exchange Reactions of Macrobicyclic Cryptands

The rate constants for exchange reactions between metal cryptate complexes, MCry1(n+), and a free cryptand, Cry2, have been determined in several solvents.Two mechanisms could be distinguished: a reaction proceeding via the free metal cation following dissociation of MCry1(n+), and a direct, bimolecular cation exchange between the two ligands.In solvents such as water, dimethylsulphoxide and dimethylformamide, which interact strongly with cations, the former pathway predominates for alkali-metal and alkaline-earth-metal cryptates.In poorly solvating media such as methanol and propylene carbonate, where dissociation rate constants are very low, bimolecular pathways make an important contribution to the overall exchange pathway.Exchange reactions of Ag(1+) cryptates show ligand-dependent rates and strong saturation effects in both methanol and dimethylsulphoxide.

Cryptand Exchange Kinetics

The rate constants for some reactions between a metal cryptate MCry1n+ and a free cryptand Cry2 has been determined.For the case when Mn+ = Tl+, Ca2+, Cry1 = (2,2,2), (2B,2,2) and Cry2 = (2,2,1) in water or water-methanol mixtures, the observed rate constant correspond to that of the dissociation of MCry1n+.However, the exchange reactions Pb(2,1,1)2+ + (2,2,1) and Pb(2,1,1)2+ + (2,2,2) in MeOH present rates that are much larger than the dissociation rate of Pb(2,1,1)2+.A mechanism involving a bimolecular reaction between cryptate and free cryptand is proposed.

Complexes of macrocyclic compounds

Novel macrocyclic (monocyclic and bicyclic) compounds having nitrogen bridgehead atoms and having in the hydrocarbon bridging chains at least two additional hetero atoms selected from the group consisting of sulfur, oxygen, and nitrogen, when admixed with a compatible cation-donor compound form stable cation-containing macrocyclic complexes which, in turn, can be conveniently dissociated by addition of acid or a quaternizing agent. The novel macrocyclics are valuable for use in the same way and for the same purposes as chelating agents.

Monocyclic macrocyclic compounds and complexes thereof

Novel monocyclic macrocyclic compounds having nitrogen bridgehead atoms and having in the hydrocarbon bridging chains at least two additional hetero atoms selected from the group consisting of sulfur, oxygen, and nitrogen, when admixed with a compatible cation-donor compound form stable cation-containing macrocyclic complexes which, in turn, can be conveniently dissociated by addition of acid or a quaternizing agent. The novel macrocyclics are valuable for use in the same way and for the same purposes as chelating agents.