112193-79-0

Upstream product

• 23539-10-8 N¹-(2-aminoethyl)-N1-benzylethane-1,2-diamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 3634-89-7 N-(p-toluenesulfonyl)aziridine 
• 100-46-9 benzylamine 
• 77429-97-1 N¹,N⁵-ditosyl-3-azapentane-1,5-diamine 
• 100-39-0 benzyl bromide 
• 6367-75-5 2-(tosylamino)ethyl p-toluenesulfonate 
• 80-39-7 N-ethyl-4-methyl-benzenesulfonamide 
• 4556-90-5 N-(2-bromo-ethyl)-4-methyl-benzenesulfonamide 

Downstream Products

• 112193-80-3 1-benzyl-4,7,10-tris(p-toluenesulfonyl)-1,4,7,10-tetraazacyclododecane 
• 1245029-72-4 Ti(N(CH₂CH₂NSO₂C₆H₄CH₃)2CH₂C₆H₅)(OCH(CH₃)2)2 
• 1245029-69-9 Ti(N(CH₂CH₂NSO₂C₆H₄CH₃)2CH₂C₆H₅)(N(CH₃)2)2 
• 1588866-18-5 C₃₂H₃₆AgN₄O₄S₂⁽¹⁺⁾*CF₃O₃S^(1-) 
• 1588866-19-6 C₃₂H₃₆AgN₄O₄S₂⁽¹⁺⁾*C₂F₆NO₄S₂^(1-) 
• 129135-32-6 6-benzyl-3,9-ditosyl-3,6,9,15-tetraazabicyclo[9,3,1]pentadeca-1⁽¹⁵⁾,11,13-triene 
• 1269621-50-2 [In(CH₂SiMe₃)(PhCH₂N(CH₂CH₂NTs)2)] 
• 1215088-50-8 [Al(2-N,N-dimethylaminoethoxide)((N(Ts)CH₂CH₂)2NCH₂Ph)] 
• 1215088-47-3 [Al(2-aminoethoxide)((N(Ts)CH₂CH₂)2NCH₂Ph)] 
• 1215088-38-2 [AlEt((N(SO₂Tol)CH₂CH₂)2NCH₂Ph)] 
• 1230242-09-7 1,7-di-(p-toluenesulfonyl)-4-benzyl-10-trityl-1,4,7,10-tetraazacyclotetradecane 
• 164913-04-6 N¹¹-benzyl-1,21-diphthalimido-N⁴,N⁸,N¹⁴,N¹⁸-tetratosyl-4,8,11,14,18-pentaazaheneicosane 
• 164913-05-7 N¹¹-benzyl-N¹,N²¹-diformyl-N⁴,N⁸,N¹⁴,N¹⁸-tetratosyl-4,8,11,14,18-pentaaza-1,21-heneicosanediamine 
• 164913-36-4 N¹,N⁴,N⁷,N¹⁰,N¹³-pentatosyl-1,4,7,10,13,16-hexaazacyclooctadecane 

Relevant academic research and scientific papers

New synthetic routes for 1-benzyl-1,4,7,10-tetraazacyclododecane and 1,4,7,10-tetraazacyclododecane-1-acetic acid ethyl ester, important starting materials for metal-coded DOTA-based affinity tags

Two improved routes to synthesize 1-benzyl-1,4,7,10-tetraazacyclododecane (6) and 1,4,7,10-tetraazacyclododecane-1-acetic acid ethyl ester (11) are described as well as the synthesis of 1-{2-[4-(maleimido-N-propylacetamidobutyl) amino]-2-oxoethyl}-1,4,7,10-tetraazacyclododecane-4,7,10-triacetic acid (17) and its Y, Ho, Tm, and Lu complexes. The 1H and 13C NMR spectra of the new compounds as well as the single crystal X-ray structure analyses of the intermediates 4-benzyl-1,7-bis(p-toluenesulfonyl) diethylenetriamine (3) and 1,4,7-tris(p-toluenesulfonyl)diethylenetriamine (7) are reported and discussed. The rare earth complexes of 17 have been characterized by 1H NMR spectroscopy and MALDI-TOF mass spectrometry.

Lanthanide(III) Complexes of Novel Mixed Carboxylic-Phosphorus Acid Derivatives of Diethylenetriamine: A Step towards More Efficient MRI Contrast Agents

Three novel phosphorus-containing analogues of H5DTPA (DTPA = diethylenetriaminepentaacetate) were synthesised (H6L1, H5L2, H5L3). These compounds have a -CH2-P(O)(OH)-R function (R = OH, Ph, CH2NBn2) attached to the central nitrogen atom of the diethylenetriamine backbone. An NMR study reveals that these ligands bind to lanthanide(III) ions in an octadentate fashion through the three nitrogen atoms, a P-O oxygen atom and four carboxylate oxygen atoms. The complexed ligand occurs in several enantiomeric forms due to the chirality of the central nitrogen atom and the phosphorus atom upon coordination. All lanthanide complexes studied have one coordinated water molecule. The residence times (τM 298) of the coordinated water molecules in the gadolinium(III) complexes of H6L1 and H5L2 are 88 and 92 ns, respectively, which are close to the optimum. This is particularly important upon covalent and noncovalent attachment of these Gd3+ chelates to polymers. The relaxivity of the complexes studied is further enhanced by the presence of at least two water molecules in the second coordination sphere of the Gd3+ ion, which are probably bound to the phosphonate/phosphinate moiety by hydrogen bonds. The complex [Gd(L 3)(H2O)]2- shows strong binding ability to HSA, and the adduct has a relaxivity comparable to MS-325 (40 s-1mM -1 at 40MHz, 37°C) even though it has a less favourable τM value (685 ns). Transmetallation experiments with Zn 2+ indicate that the complexes have a kinetic stability that is comparable to-or better than-those of [Gd(dtpa)(H2O)]2- and [Gd(dtpa-bma)(H2O)].

Mild regiospecific synthesis of 1-alkoxy-isochromenes catalyzed by well-defined [silver(I)(pyridine-containing ligand)] complexes

The synthesis of 3-substituted-1-alkoxyisochromenes starting from 2-alkynylbenzaldehydes and different alcohols is reported. The reaction is catalyzed by a silver(I) complex with an original macrocyclic pyridine-containing ligand. The approach is characterized by absolute regioselectivity, mild reaction conditions, good to excellent reaction yields, cleanness of the reaction, and reduced purification steps. The reaction mechanism was investigated by in-depth 1H NMR experiments and an aimed trapping experiment.

Ring opening of N-sulfonyl aziridines by amines in silica-water

Ring opening reactions of N-sulfonyl aziridines by primary and secondary amines in silica gel (SG)-water system were achieved, which provided a mild, practical and environmentally benign method to synthesize mono- and bis-sulfonyl substituted amines. When

Asymmetric cyclopropanation of olefins catalysed by Cu(i) complexes of chiral pyridine-containing macrocyclic ligands (Pc-L*)

The synthesis and characterisation of copper(i) complexes of chiral pyridine-containing macrocyclic ligands (Pc-L*) and their use as catalysts in asymmetric cyclopropanation reactions are reported. All ligands and metal complexes were fully characterised, including crystal structures of some species determined by X-ray diffraction on single crystals. This allowed characterising the very different conformations of the macrocycles which could be induced by different substituents or by metal complexation. The strategy adopted for the ligand synthesis is very flexible allowing several structural modifications. A small library of macrocyclic ligands possessing the same donor properties but with either C1 or C2 symmetry was synthesized. Cyclopropane products with both aromatic and aliphatic olefins were obtained in good yields and enantiomeric excesses up to 99%.

Henry reaction catalyzed by copper(I) complexes of a new pyridine-containing macrocyclic ligand

The synthesis and characterization of copper(I) complexes of the novel pyridine-containing macrocyclic ligand (PC-L) and their use as catalysts in the Henry reaction are reported. The pyridine-based 12-membered tetraaza macrocyclic (PC-L) ligand 1 can be

Sulfonamide-supported aluminum catalysts for the ring-opening polymerization of rac-lactide

The synthesis, structures, and ring-opening polymerization (ROP) capability of a wide range of sulfonamide-supported aluminum alkyl and alkoxide complexes are reported. The synthesis of the new protio-ligands PhCH2N(CH 2CH2NHSO2R)2 (R = ToI (15, H 2N2TsNph) or Me (16, H 2N2MsNph)) is described. These and the previously reported 1,2-C6H10(NHSO2R) 2 (R = Tol (11, H2CyN2Ts) or Mes (12, H2CyN2so2Mes)) and RCH 2N(CH2CH2NHSO2TOl)2 (R = MeOCH2 (13, H2N2TSNOMe) or 2-NC5H4 (14, H2N2 TsNpy)) reacted with AlEt3 to form Al(CyN 2Ts)Et(THF) (17), Al(CyN2SO2Mes) Et(THF) (18), and Al(N2TsNR)Et (R = Ph (19), OMe (20), or py (21)), respectively. Subsequent reaction of these ethyl complexes with R'OH (R' = 1Pr or Bn) resulted in protonolysis of the sulfonamide supporting ligands to yield a mixture of products including Al(OR')3- In contrast, reaction of Al(OR')Et2 (R' = 1Pr, Bn, CH2CH2NH2, or CH2CH 2NMe2) with various protio-ligands formed the sulfonamide-supported alkoxides Al(N2TsN py)(OR') (R' = 1Pr (22) or Bn (23)), Al(N2 MsNph)(OR') (R' = Pr (26) or Bn (27)), Al(N 2TsNR)(OCH2CH2NH 2) (R = Ph (29), OMe (30), or py (31)), Al(CyN2 Ts)(OCH2CH2NMe2) (32), and Al(N 2TsNph)(OCH2CH2NMe 2) (33). Unexpectedly, reaction OfAl(OTr)Et2 with H 2N2TsNOMe led to O-demethylation of the sulfonamide ligand. Reaction of AlMe2Cl with H2N 2TsNph gave [Al(NTs 2Nph)Cl]2 (28). X-ray diffraction studies revealed four- or five-coordinate C.v-symmetric structures for 17-21, a five-coordinate C2-symmetric sulfonamide-bridged dimer for 28, and a five-coordinate C,-symmetric monomer for 30 stabilized by intramolecular hydrogen bonding between the sulfonyl oxygens and the amine protons. Compounds 19, 21, 22-27, and 29-33 are all catalysts for the ROP of rac-lactide, with the alkoxide compounds 22-27 and 32 giving well-defined molecular weights and molecular weight distributions. These compounds were also active in the melt at 130 °C, giving atactic poly(rac-lactide) with moderate to narrow PDIs and extremely good control of Mn and high activity in the case of 23.

Neuroprotection and cardioprotection afforded by chelators with high affinity and specificity for cations of first transition series elements

Compounds that demonstrate chelation affinity and selectivity for first transition series elements are administered to patients suffering from such conditions as ischemia, prolonged seizures and trauma to provide neuroprotection, cardioprotection, or both. These compounds when administered form complexes with chelatable iron and copper cations and thereby mitigate the ability of these cations to catalyze Haber-Weiss reactions that form toxic hydroxy free radicals that cause tissue injury. These compounds also form complexes with chelatable zinc cations thereby inhibiting the cytotoxicity associated with excess chelatable zinc.

Compounds with chelation affinity and selectivity for first transition elements and their use in cosmetics and personal care products, inhibition of metalloenzymes, and inhibition of reperfusion injury

This invention involves the use of a class of compounds with chelation affinity and selectivity for first transition series elements. Application or administration of the free or conjugated compound, or physiological salts of the free or conjugated compound, results in decrease of the bioavailability and/or chemical action of first transition series elements. These characteristics make such compounds useful in cosmetics and personal care products to decrease odor arising from microbial growth on body surfaces and in body cavities, decrease microbial growth on teeth, plaque, and gums that cause tooth decay and gum disease, inhibition of oxidative damage to the skin, inhibition of enzymatic action of metalloenzymes dependent on first transition series elements, and inhibition of reperfusion injury.

Multi-layer macromonocyclic polyamines. I. Molecular design and synthesis of component monocyclic precursors

We designed 'multi-layer macromonocyclic polyamines' which might be appropriate polymorphismic molecular scaffolds as host-molecules in ionic or molecular interaction with small or large guest ions or molecules. In polymorphismic molecules, several macromonocyclic polyamines with the same and/or different ring sizes and nitrogen contents are connected to each other by alkylene spacers with various length of the chain. Actual target molecules are characterized by possessing methylene chain arrays of natural polyamines, and we have synthesized from simple starting materials fourteen component macromonocycles with various sizes, 12- to 34-membered rings containing three to eight nitrogen atoms, as essential building blocks required for construction of multi-layer molecules. Our method of synthesis was shown to be very efficient. In a final step, the N-protecting benzyl group was successfully removed by hydrogenation on 10%-Pd/C under 4 kg cm-2 H2 to give the cyclic amine precursors, which could be internal and terminal components in the architecture of the multi-layer molecules. The structures of synthesized compounds were characterized and confirmed by EA, 1H NMR, SIMS, and FAB(+) mass spectrometry.