24772-41-6

Usage

Uses

Used in Medicinal Chemistry:
1,5,9,13-Tetraazacyclohexadecane is used as a chelating agent for metal ions in the development of MRI contrast agents, enhancing the imaging capabilities of medical diagnostics.
Used in Drug Delivery Systems:
1,5,9,13-Tetraazacyclohexadecane is used as a carrier for drug delivery, improving the bioavailability and therapeutic outcomes of various pharmaceuticals.
Used in Metal Extraction Processes:
1,5,9,13-Tetraazacyclohexadecane is used as a chelating agent in metal extraction processes, facilitating the separation and purification of metal ions.
Used in Antibacterial Applications:
1,5,9,13-Tetraazacyclohexadecane and its complexes are used as antibacterial agents, exhibiting potential activity against various bacterial strains.
Used in Antifungal Applications:
1,5,9,13-Tetraazacyclohexadecane and its complexes are used as antifungal agents, showing potential activity against various fungal strains.
Used in Anticancer Applications:
1,5,9,13-Tetraazacyclohexadecane and its complexes are used as anticancer agents, demonstrating potential activity against various types of cancer.
Used in Catalysis:
1,5,9,13-Tetraazacyclohexadecane is used as a ligand in catalytic processes, enhancing the efficiency and selectivity of chemical reactions.
Used in Coordination Chemistry:
1,5,9,13-Tetraazacyclohexadecane is used in the synthesis and study of coordination compounds, contributing to the understanding of metal-ligand interactions and their properties.

Upstream product

• 144534-73-6 1,5,9,13-Tetrakis-trifluoromethanesulfonyl-1,5,9,13-tetraaza-cyclohexadecane 
• 56234-53-8 1,5,9,13-tetratosyl-1,5,9,13-tetraazacyclohexadecane 
• 60-29-7 diethyl ether 
• 144534-69-0 C,C,C-Trifluoro-N-(3-trifluoromethanesulfonylamino-propyl)-N-{3-[trifluoromethanesulfonyl-(3-trifluoromethanesulfonylamino-propyl)-amino]-propyl}-methanesulfonamide 
• 67341-38-2 N,N'-bis<3-(tosylamino)propyl>-N,N'-ditosyl-1,3-propanediamine 
• 4605-14-5 N,N'-bis-(3-aminopropyl)-1,3-propanediamine 

Downstream Products

• 131426-21-6 N,N',N'',N'''-tetrakis(2-N-tosylaminoethyl)-1,5,9,13-tetra-azacyclohexaadecane 
• 133563-61-8 1-Benzyl-1,5,9,13-tetraaza-cyclohexadecane 
• 918412-00-7 ([16]aneN₄)Zn(phenylmethanethiolate) perchlorate 
• 918412-02-9 ([16]aneN₄)Zn(4-methylbenzenethiolate) perchlorate 

Relevant academic research and scientific papers

A convenient synthesis of isocyclam and [16]aneN4 and the photophysics of their dicyanochromium(III) complexes

The syntheses of the tetraazamacrocyclic ligands 1,4,7,11-tetraazacyclotetradecane (isocyclam) and 1,5,9,13-tetraazacyclohexadecane ([16]aneN4) in two steps starting from the corresponding tetraamine and diethylmalonate is reported. The trans-dicyanochromium(III) complexes, trans-[Cr(isocyclam)(CN)2]PF6 and trans-[Cr([16]aneN4)(CN)2]PF6 have also been prepared. Both are 2Eg emitters with 0-0 band emission wavelengths at 721.2 and 704.8 nm, respectively. The isocyclam complex has a room temperature excited state lifetime of 147 μs in aqueous solution which increases to 215 μs upon macrocyclic N-H deuteration, whereas the corresponding lifetime of the [16]aneN4 complex is 25 μs and is unaffected by macrocyclic N-H deuteration. The implications of the temperature dependence of the excited state lifetimes are also presented.

Triflamides for protection and cyclization of tetraamines to tetraazamacrocycles

A facile two-step synthesis of tetraazamacrocycles is reported starting from trifluoromethanesulfonyl derivatives of linear tetraamines. After cyclization, the macrocycle was deprotected using sodium in liquid ammonia.

Studies on biologically potent tetraazamacrocyclic complexes of bivalent tin

Fourteen- to eighteen-membered tetraamide macrocyclic ligands N4L1-N4L4 have been prepared by the condensation of 1,2-diaminoethane or 1,3-diaminopropane with malonic or succinic acid in the presence of condensing reagents dicyclohexylcarbodiimide and 4-dimethylaminopyridine. On reduction, these macrocyclic ligands give a new series of tetraazamacrocycles MacL1-MacL4 which form complexes with tin(II) chloride. The ligands and their complexes were characterized by elemental analyses, molecular weight determinations, infrared and 1H NMR spectral studies. The hexacoordinated state for tin has been confirmed by spectral studies. An octahedral geometry for these complexes has been proposed as the binding sites are the nitrogen atoms of the macrocycles. On the basis of the chemical composition the representation of the complexes as [Sn(MacLn)Cl2] (n = 1-4) has been established. The ligands and their complexes also have been screened for their antifungal and antibacterial activities and the findings have been reported and explained.

Enthalpic and Entropic Contributions in the reactions of Hydrogen, Copper(II), and Nickel(II) Ions with the Macrocycle 1,5,9,13-Tetra-azacyclohexadecane

Enthalpies of protonation of 1,5,9,13-tetra-azacyclohexadecane (L1) have been determined by a continous titration calorimetric technique and the corresponding entropy values obtained by combination with the free-energy data.The stepwise enthalpies are all very similar, and are interpreted in terms of the ability of the amino-groups to behave independently of each other towards protons.The stability constants of the complexes (CuL1)2+ and(CuHL1)3+ have been determined by potentiometry at 25 deg C in o.5 mol dm-3 K.The enthalpies of formation of the copper(II) and nickel(II) complexes of L1 have been determined by batch microcalorimetry, and are discussed in terms of the unfavourable free-ligand conformation and the presence of hindered chelate rings in the complexes.Finally the stability of the (CuL1)2+ complex is compared with that of the corresponding complex with the acyclic ligand 4,8-diazaundecane-1,11-diamine; the greater stability of the former complex is attributed to a very favourable entropy term and to a slightly favourable enthalpy term.

Manganese complexes of nitrogen-containing macrocyclic ligands effective as catalysts for dismutating superoxide

The present invention is directed to low molecular weight mimics of superoxide dismutase (SOD) represented by the formula: STR1 wherein R, R', R1, R'1, R2, R'2, R3, R'3, R4, R'4, R5, R'5, R6, R'6, R7, R'7, R8, R'8, R9, and R'9 and X, Y, Z and n are as defined herein, useful as therapeutic agents for inflammatory disease states and disorders, ischemic/reperfusion injury, stroke, atherosclerosis, hypertension and all other conditions of oxidant-induced tissue damage or injury.

Methods of preparing manganese complexes of nitrogen-containing macrocyclic ligands

The present invention is directed to low molecular weight mimics of superoxide dismutase (SOD) represented by the formula: STR1 wherein R, R', R1, R'1, R2, R'2, R3, R'3, R4, R'4, R5, R'5, R6, R'6, R7, R'7, R8, R'8, R9, and R'9 and X, Y, Z and n are as defined herein, useful as therapeutic agents for inflammatory disease states and disorders, ischemic/reperfusion injury, stroke, atherosclerosis, hypertension and all other conditions of oxidant-induced tissue damage or injury.

Studies on the interaction of iron(II), nickel(II), copper(II) and zinc(II) with tetraazamacrocycles

The condensation of aliphatic diamines H2N(CH2)nNH2 (n = 2-3) with dicarboxylic acid HOOC - (CH2)n - COOH (n=1-2) in the presence of dicyclohexyl-carbodiimide and 4-(dimethylamino)pyridine results in new types of 14-18 membered tetraamide macrocyclic ligands 1a-1d. These compounds on reduction with LiAlH4 yield a series of tetraazamacrocycles 2a-2d which form complexes with Fe(II), Ni(II), Cu(II) and Zn(II). The ligands and their complexes have been characterized by elemental analyses, mass, IR, 1H NMR, UV/Vis, EPR spectroscopic, molar conductance and magnetic moment data. An octahedral geometry around the metal ion is suggested for [M2aCl2][M2dCl2], where M = Fe(II) and Ni(II) while a square-planar and a tetrahedral geometry is proposed for [M2a]Cl2-[M2d]Cl2 for M = Cu(II) and Zn(II).

Synthesis and characterization of various unsubstituted and mono-N-substituted tetraazamacrocycles

Syntheses of tetraazamacrocycles have been carried out by using p-toluenesulfonyl chloride as protective group.The and were also obtained by the template synthesis.Mono-N-functionalization of tetraazamacrocycles was accomplished by reaction of a fivefold excess of the free macrocycles with 1 equivalent of a suitable alkylating or arylating reagent.The key point of the synthesis lies in the use of an excess of the macrocycle over the substituting reactants to reduce the formation of polysubstituted derivatives, and in the easy separation of the excess of unreacted macrocycle.All the products were characterized on the basis of spectral studies (1H and 13C NMR, including 2D NMR and NOE difference studies) and mass spectrometry.Key words: tetraazamacrocycles, improved synthesis, protective group, N-tosylation, template synthesis, NOE difference spectroscopy.

Macrocyclic polyamines

Macrocyclic polyamines containing 3-7 nitrogen atoms in the ring and destablized to complex formation by (1) an asymmetric ring and/or (2) provision of nitrogen atoms in excess of that required for complex formation are described. The compounds can be used to extract metal ions from solution. The metal complexes are thermally activated curing agents for epoxy resins.