210303-79-0

Upstream product

• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 111-40-0 3-azapentane-1,5-diamine 

Downstream Products

• 856134-22-0 9-[(trityloxy)methyl]-1,4,7-triazecane-1,4,7-tris-(2-nitrobenzenesulfonamide) 
• 910449-78-4 12-benzyloxy-3,6,9-tris(2-nitrobenzenesulfonyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1⁽¹⁵⁾,11,13-triene 
• 1426819-69-3 12-benzyloxy-3,6,9-tris(2-nitrobenzenesulfonyl)-3,6,9,15-tetraazabicyclo[9.3.1]penta-deca-⁽¹⁵⁾,11,13-triene 
• 859502-09-3 3-[1,4,7-tris-(2-nitro-benzenesulfonyl)-[1,4,7]triazecan-9-yl]-propan-1-ol 
• 859502-08-2 [1,4,7-tris-(2-nitro-benzenesulfonyl)-[1,4,7]triazecan-9-yl]-methanol 
• 942200-55-7 3-(4-iodophenoxy)-tris-(2-nitrobenzenesulfonyl)-1,4,7-triazacyclodecane 
• 541533-50-0 12-dodecyloxy-3,6,9-tris(2-nitrophenylsulfonyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1⁽¹⁵⁾,11,13-triene 
• 290326-06-6 3,6,9-tris-(2-nitro-benzenesulfonyl)-3,6,9,15-tetraaza-bicyclo[9.3.1]pentadeca-1⁽¹⁴⁾,11⁽¹⁵⁾,12-triene 
• 227457-58-1 12-(4-Bromobenzyloxy)-3,6,9-tris(2-nitrobenzenesulfonyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1⁽¹⁵⁾,11,13-triene 

Relevant academic research and scientific papers

Structural, spectral, and electrochemical properties of nickel(II), copper(II), and zinc(II) complexes containing 12-membered pyridine- and pyridol-based tetra-aza macrocycles

The structural, electronic, and electrochemical properties of a series of novel 12-membered pyridine- and pyridol-based tetra-aza transition-metal (Ni, Cu, Zn) complexes {[MII(L1)Cl](ClO4), [M II(L2)Cl](ClO4), a

Synthesis of thiacrown and azacrown ethers based on a spiroacetal framework

A novel class of thiacrown and azacrown ethers incorporating the 1,7-dioxaspiro[5.5]undecane spiroacetal ring system was prepared by reaction of ditosylate 5 with the appropriate dithiols 9a-c or protected diamine 12a. Spiroacetal ditosylate 5 in turn, wa

An efficient synthesis of pyridine containing triaza-macrocyclic triacetate ligand and luminescence properties of its europium(III) complex

Reaction of diethylenetriamine with 2-nitrobenzenesulfonyl chloride leads to an activated and protected compound that could be cyclized to N-protected aza-macrocycle. After a smooth deprotection step, the macrocycle was alkylated with chloroacetic acid le

A potent antioxidant small molecule aimed at targeting metal-based oxidative stress in neurodegenerative disorders

Metal-ion misregulation and oxidative stress have been linked to the progressive neurological decline associated with multiple neurodegenerative disorders. Transition metal-mediated oxidation of biomolecules via Fenton chemical reactions plays a role in d

Lipophilic chelates and their use in imaging

The invention relates to chelate compounds which can be used in MRI, the chelates being intended to be conveyed by lipophilic transporters, such as lipid nanoparticles or liposomes. The invention also relates to compounds comprising, in association, these chelates and these transporters, if appropriate connected via chemical bonding groups, and to their use in diagnostic imaging, it being possible for this association additionally to comprise biological targeting markers, denoted biovectors.

Polyaza[n](1,4)naphthalenophanes and polyaza[n](9,10)anthracenophanes

A series of polyaza[n](1,4)naphthalenophanes and polyaza[n](9,10)anthracenophanes have been prepared by using the Fukuyama's protecting group (2- or 4-nitrophenyl sulfonyl) in a one-pot cyclization-deprotection reaction. Global yields for the purified products are comparable with those obtained for other polyazacyclophanes using the tosyl group as the amine protecting group. Their structural study has been carried-out by NMR showing a high rigidity for the smaller cycles and a more dynamic behaviour for the largest member of the series. The free energy barrier for the rotational equilibrium for compound 25 is about 3kcal/mol lower than that calculated for analogous N-tosylated macrocycles.

A highly chemoselective protection and activation of primary amines in polyamine

Functionalization of polyamines containing both primary and secondary amine moieties could be achieved with the use of 2-nitrobenzenesulfonyl chloride. In the presence of a secondary amine, the primary amine groups are selectively transformed into the cor

Contrast agents for magnetic resonance imaging: A novel route to enhanced relaxivities based on the interaction of a Gd(III) chelate with poly-β-cyclodextrins

This study proposes a novel route to improved contrast agents for magnetic resonance imaging (MRI) applications based on the formation of a non-covalent adduct between a paramagnetic complex and an exogeneous macromolecule. For this purpose a 12-membered pyridine-containing triacerate macrocyclic ligand with a p-bromobenzyloxy substituent on the pyridine moiety was synthesized. The Gd(III) complex containing this ligand shows a relaxivity of 8.25mM-1S-1 at 20MHz and 25°C. The hydrophobic p-bromo- benzyloxy moiety promotes the interaction of the chelate with human serum albumin (HSA) (K(a) x 102M-1) and with β-cyclodextrin (K(a) = 8 x 102M- 1). Upon replacing β-cyclodextrin with a poly-β-cyclodextrin substrate (MW = ca. 6000 Da) a further relaxation enhancement is detected as a consequence of the increased molecular size of the resulting inclusion compound. In a typical experiment in blood serum, the observed relaxivity is 32mM-1S-1 (20 MHz, 25°C) when the concentrations are as follows: Gd(III) chelate I mM, poly-β-cyclodextrin 10mM, HSA 0.58mm. Under these conditions the Gd(III) chelate is mainly present as an inclusion compound with the poly-β-CD. This finding suggests a potential use for such a Gd(III) chelate/poly-β-CD system in MR angiographic applications. This study proposes a novel route to improved contrast agents for magnetic resonance imaging (MRI) applications based on the formation of a non-covalent adduct between a paramagnetic complex and an exogeneous macromolecule. For this purpose a 12-membered pyridine-containing triacetate macrocyclic ligand with a p-bromo-benzyloxy substituent on the pyridine moiety was synthesized. The GdIII complex containing this ligand shows a relaxivity of 8.25 mM-1 s-1 at 20 MHz and 25 °C. The hydrophobic p-bromo-benzyloxy moiety promotes the interaction of the chelate with human serum albumin (HSA) (Ka = 4×102 M-1) and with β-cyclodextrin (Ka = 8×102 M-1). Upon replacing β-cyclodextrin with a poly-β-cyclodextrin substrate (MW = ca. 6000 Da) a further relaxation enhancement is detected as a consequence of the increased molecular size of the resulting inclusion compound. In a typical experiment in blood serum, the observed relaxivity is 32 mM-1 s-1 (20 MHz, 25 °C) when the concentrations are as follows: GdIII chelate 1 mM, poly-β-cyclodextrin 10 mM, HSA 0.58 mM. Under these conditions the GdIII chelate is mainly present as an inclusion compound with the poly-β-CD. This finding suggests a potential use for such a GdIII chelate/poly-β-CD system in MR angiographic applications.

One-pot synthesis of polyaza[n]naphthalenophanes and polyaza[n]anthracenophanes

Pernosylated polyaza[n]cyclophanes 13-20 were prepared by a Richman- Atkins modified methodology. Deprotection under mild conditions gave polyaza[n]cyclophanes 21-28. This methodology allows for the preparation of cyclophanes containing labile C-N bonds.