75920-10-4

Basic information

• Product Name: 1,4,8,11-Tetraazatricyclo[9.3.1.1(4,8)]hexadecane
• Synonyms: 1,4,8,11-Tetraazatricyclo[9.3.1.1(4,8)]hexadecane
• CAS NO: 75920-10-4
• Molecular Formula: C₁₂H₂₄N₄
• Molecular Weight: 224.35
• Mol File: 75920-10-4.mol
• Article Data: 26

Chemical Properties

• Melting Point: 83-85°C
• Boiling Point: 324.6°C at 760 mmHg
• Flash Point: 136.2°C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 0.000242mmHg at 25°C
• Refractive Index: 1.596
• Sensitive: Hygroscopic
• CAS DataBase Reference: 1,4,8,11-Tetraazatricyclo[9.3.1.1(4,8)]hexadecane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4,8,11-Tetraazatricyclo[9.3.1.1(4,8)]hexadecane(75920-10-4)
• EPA Substance Registry System: 1,4,8,11-Tetraazatricyclo[9.3.1.1(4,8)]hexadecane(75920-10-4)

Safety Data

• Hazardous Substances Data: 75920-10-4(Hazardous Substances Data)

Usage

General Description

1,4,8,11-Tetraazatricyclo[9.3.1.1(4,8)]hexadecane, also known as TATD, is a complex organic compound with a unique molecular structure. It is a cage-like molecule consisting of carbon and nitrogen atoms arranged in a three-dimensional configuration. TATD has been studied for its potential use in various applications, including as a ligand for metal ion coordination, a catalyst for organic reactions, and as a building block for the synthesis of novel molecular architectures. Its unique structure and properties make it an intriguing area of study for researchers in the field of organic and inorganic chemistry.

InChI:InChI=1/C12H24N4/c1-3-13-7-9-15-5-2-6-16(12-15)10-8-14(4-1)11-13/h1-12H2

Upstream product

• 295-37-4 1,4,8,11-Tetraazacyclotetradecane 
• 50-00-0 formaldehyd 
• 75-09-2 dichloromethane 
• 199275-80-4 1,4,8,11-tetraazabicyclo[9.3.1]pentadecane 
• 294-90-6 1,4,7,10-tetraazacyclododecan 

Downstream Products

• 214078-92-9 1,8-Dimethyl-1,4,8,11-tetraazacyclotetradecane 
• 121187-41-5 1,4-dimethyl-1,4,8,11-tetraazacyclotetradecane 
• 41203-22-9 1,4,8,11-tetramethyl-1,4,8,11-tetra-azacyclotetradecane 
• 214078-93-0 1,8-Dibenzyl-1,4,8,11-tetraazacyclotetradecane 
• 1227479-17-5 1,8-(4-tert-butylbenzyl)-1,4,8,11-tetraazacyclotetradecane 
• 1227479-18-6 1,8-bis(4-(trifluoromethyl)benzyl)-1,4,8,11-tetraazacyclotetradecane 
• 1186198-19-5 H₂(3,5-di(tert-butyl)benzyl)cyclam 
• 1186198-18-4 H₂(3,5-dimethylbenzyl)cyclam 
• 1221749-39-8 4,11-bis(1-benzyl-1H-[1,2,3]triazol-4-ylmethyl)-1,4,8,11-tetraazacyclotetradecane-1,8-dicarboxylic acid di-tert-butyl ester 

Relevant articles and documents

Kinetics Are Crucial When Targeting Copper Ions to Fight Alzheimer's Disease: An Illustration with Azamacrocyclic Ligands

Targeting copper ions to either remove or redistribute them is currently viewed as a possible therapeutic strategy in the context of Alzheimer's disease (AD). Thermodynamic parameters, as for instance the copper(II) affinity of the drug candidate or the copper(II) over zinc(II) selectivity, are considered in the design of the drug candidate. In contrast, kinetic factors have been overlooked despite their probable high importance. In the present article, we use a series of azamacrocyclic ligands to demonstrate that kinetic issues must be taken into account when designing copper-targeting drug candidates in the context of AD.

Revival of TE2A; A better chelate for Cu(II) ions than TETA?

A highly effective synthetic route for TE2A was developed and the 64Cu-labeled TE2A complexes showed higher kinetic inertness and faster clearance than most commonly used TETA analogs.

New heterobimetallic Cu(II)/Mn(II) complexes with trans-1,8-cyclam derivatives: Synthesis, characterization, magnetic properties and crystal structures of (μ2-Chloro)-(dpc)-copper(II)-trichloro-manganese(II) and two polymorphs of (μ2-Chloro)-(dac)-copper(II)-trichloro-manganese(II)

Two derivatives of cyclam (cyclam = 1,4,8,11-tetraazacyclotetradecane) with propyl- or allyl- (prop-2-en-1-yl) substituents on nitrogen atoms in trans positions, namely 1,8-dipropyl-1,4,8,11-tetraazacyclotetradecane (dpc) and 1,8-diallyl-1,4,8,11-tetraazacyclotetradecane (dac) were prepared and characterized by IR, 1H NMR and 13C NMR spectroscopy. Reaction of dpc and dac with copper(II) chloride gives compounds [Cu(dpc)(H2O)2]Cl2 (1) and [Cu(dac)(H2O)2]Cl2 (3) with similar crystal structures. Compounds 1 and 3 were used as precursors in the synthesis of Cu(II)/Mn(II) complexes 2, 4a and 4b. Prepared complexes were characterized by IR spectroscopy, elemental analysis and their crystal structures were determined using single crystal X-ray analysis. Compounds 4a and 4b are polymorphs, both crystallize in the monoclinic crystal system and the main difference in their crystal structures is in steric arrangement of metal centres within a chain. Moreover, measurements of magnetic susceptibility and Broken Symmetry DFT calculations (BS DFT calculations) carried out for bimetallic complexes 2 and 4a showed that a ferromagnetic exchange interaction J/kB = 2.28 K and J/kB = 2.34 K, respectively, exists within the dinuclear units.

Towards the development of a targeted albumin-binding radioligand: Synthesis, radiolabelling and preliminary in vivo studies

Introduction: The compound named 4-[10-(4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanamido)decyl]-11-[10-(β,D-glucopyranos-1-yl)-1-oxodecyl]-1,4,8,11-tetraazacyclotetradecane-1,8-diacetic acid is a newly synthesised molecule capable of binding in vivo to

Tetraazamacrocyclic derivatives and their metal complexes as antileishmanial leads

A total of 44 bis-aryl-monocyclic polyamines, monoaryl-monocyclic polyamines and their transition metal complexes were prepared, chemically characterized, and screened in vitro against the Leishmania donovani promastigotes, axenic amastigotes and intracellular amastigotes in THP1 cells. The IC50 and/or IC90 values showed that 10 compounds were similarly active at about 2-fold less potent than known drug pentamidine against promastigotes. The most potent compound had an IC50 of 2.82 μM (compared to 2.93 μM for pentamidine). Nine compounds were 1.1–13.6-fold more potent than pentamidine against axenic amastigotes, the most potent one being about 2-fold less potent than amphotericin B. Fourteen compounds were about 2–10 fold more potent than pentamidine, the most potent one is about 2-fold less potent than amphotericin B against intracellular amastigotes in THP1 cells. The 2 most promising compounds (FeL7Cl2 and MnL7Cl2), with strong activity against both promastigotes and amastigotes and no observable toxicity against the THP1 cells are the Fe2+- and Mn2+-complexes of a dibenzyl cyclen derivative. Only 2 of the 44 compounds showed observable cytotoxicity against THP1 cells. Tetraazamacrocyclic monocyclic polyamines represent a new class of antileishmanial lead structures that warrant follow up studies.