214078-93-0

Basic information

• Product Name: 1,8-Dibenzyl-1,4,8,11-tetraazacyclotetradecane
• Synonyms: 1,8-Dibenzyl-1,4,8,11-tetraazacyclotetradecane;1,4,8,11-Tetraazacyclotetradecane, 1,8-bis(phenylMethyl)-;1,8-Dibenzylcyclam;trans-N-Dibenzyl-Cyclam
• CAS NO: 214078-93-0
• Molecular Formula: C₂₄H₃₆N₄
• Molecular Weight: 380.57
• Mol File: 214078-93-0.mol

Chemical Properties

• Melting Point: 67-68°C
• Boiling Point: 514.1°Cat760mmHg
• Flash Point: 269°C
• Appearance: /
• Density: 1.003g/cm³
• Vapor Pressure: 1.11E-10mmHg at 25°C
• Refractive Index: 1.536
• Sensitive: Hygroscopic
• CAS DataBase Reference: 1,8-Dibenzyl-1,4,8,11-tetraazacyclotetradecane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,8-Dibenzyl-1,4,8,11-tetraazacyclotetradecane(214078-93-0)
• EPA Substance Registry System: 1,8-Dibenzyl-1,4,8,11-tetraazacyclotetradecane(214078-93-0)

Safety Data

• Hazardous Substances Data: 214078-93-0(Hazardous Substances Data)

Usage

Uses

Used in Coordination Chemistry:
1,8-Dibenzyl-1,4,8,11-tetraazacyclotetradecane is used as a chelating agent for metal ions in coordination chemistry, for its capacity to form stable complexes with various metal ions such as copper, zinc, and nickel.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 1,8-Dibenzyl-1,4,8,11-tetraazacyclotetradecane is utilized as a chelating agent for the development of medical imaging agents and for the treatment of metal ion-related diseases, given its ability to form stable complexes with biologically relevant metal ions.
Used in Catalysis:
1,8-Dibenzyl-1,4,8,11-tetraazacyclotetradecane is employed as a potential ligand in catalysis, where its unique structure can influence the selectivity and efficiency of catalytic processes.
Used in Material Science:
In material science, 1,8-Dibenzyl-1,4,8,11-tetraazacyclotetradecane is used as a component in the development of new materials with specific properties, leveraging its ability to form complexes with metal ions to create materials with tailored characteristics.
These applications highlight the versatility and value of 1,8-Dibenzyl-1,4,8,11-tetraazacyclotetradecane in contributing to advancements in various research and industrial fields.

InChI:InChI=1/C24H36N4/c1-3-9-23(10-4-1)21-27-17-7-13-26-16-20-28(18-8-14-25-15-19-27)22-24-11-5-2-6-12-24/h1-6,9-12,25-26H,7-8,13-22H2

Upstream product

• 295-37-4 1,4,8,11-Tetraazacyclotetradecane 
• 100-52-7 benzaldehyde 
• 100-39-0 benzyl bromide 
• 75920-10-4 1,4,8,11-tetraazatricyclo[9.3.1.14,8]hexadecane 

Downstream Products

• 309253-73-4 Diethyl 4,11-dibenzyl-1,4,8,11-tetraazacyclotetradecane-1-(methylphosphonate) 
• 309253-74-5 Tetraethyl 4,11-dibenzyl-1,4,8,11-tetraazacyclotetradecane-1,8-di(methylphosphonate) 
• 866414-15-5 1,8-dibenzyl-4,11-bis(tert-butoxycarbonyl)-1,4,8,11-tetraazacyclotetradecane 
• 573960-25-5 [Cu((C₃H₆)2(C₂H₄)2N₄H₂(CH₂C₆H₅)2)(NO₃)2] 
• 910803-93-9 (1,8-dibenzyl-1,4,8,11-tetraazacyclotetradecane)zirconiumdichloride 
• 1262962-74-2 (Bn₂Cyclam)Zr(NMe₂) 
• 1313239-28-9 2'-(4,11-dibenzyl-1,4,8,11-tetraazacyclotetradecan-1-yl)acetyl(tosyl)amide 
• 1415908-07-4 28,34-dibenzyl-1,7,19,25,28,34-hexaazaheptacyclo[23.6.6.2^3,6.2^20,23.1^10,14.1^10,16.1^12,16]-tetra-tetraconta-3,5,20,22,38,43-hexaene 
• 1415908-03-0 1,8-dibenzyl-4,11-bis-(4-bromobenzyl)-1,4,8,11-tetraazacyclotetradecane 
• 1415908-06-3 30,36-dibenzyl-1,8,20,27,30,36-hexaazaheptacyclo[25.6.6.1^3,7.1^11,15.1^11,17.1^13,17.1^21,25]tetra-tetraconta-3⁽⁴⁴⁾,4,6,21⁽⁴⁰⁾,22,24-hexaene 
• 1415908-02-9 1,8-dibenzyl-4,11-bis-(3-bromobenzyl)-1,4,8,11-tetraazacyclotetradecane 
• 1602923-38-5 [{H₂(PhCH₂)₂Cyclam}Zn]SO₄ 
• 1602923-41-0 [{H₂(PhCH₂)₂Cyclam}ZnCl]Cl 
• 1602923-34-1 [{H₂(PhCH₂)₂Cyclam}Cu(H₂O)₂]S 

Relevant articles and documents

CoII Complexes as Liposomal CEST Agents

Three paramagnetic CoII macrocyclic complexes containing 2-hydroxypropyl pendant groups, 1,1′,1′′,1′′′-(1,4,8,11-tetraazacyclotetradecane-1,4,8,11-tetrayl)tetrakis- (propan-2-ol) ([Co(L1)]2+, 1,1′-(4,11-dibenzyl-1,4,8,11-tetraazacyclotetradecane-1,8-diyl)bis(propan-2-ol) ([Co(L2)]2+), and 1,1′-(4,11-dibenzyl-1,4,8,11-tetraazacyclotetradecane-1,8-diyl)bis(octadecan-2-ol) ([Co(L3)]2+) were synthesized to prepare transition metal liposomal chemical exchange saturation transfer (lipoCEST) agents. In solution, ([Co(L1)]2+) forms two isomers as shown by 1H NMR spectroscopy. X-ray crystallographic studies show one isomer with 1,8-pendants in cis-configuration and a second isomer with 1,4-pendants in trans-configuration. The [Co(L2)]2+ complex has 1,8-pendants in a cis-configuration. Remarkably, the paramagnetic-induced shift of water 1H NMR resonances in the presence of the [Co(L1)]2+ complex is as large as that observed for one of the most effective LnIII water proton shift agents. Incorporation of [Co(L1)]2+ into the liposome aqueous core, followed by dialysis against a solution of 300 mOsm L?1 produces a CEST peak at 3.5 ppm. Incorporation of the amphiphilic [Co(L3)]2+ complex into the liposome bilayer produces a more highly shifted CEST peak at ?13 ppm. Taken together, these data demonstrate the feasibility of preparing CoII lipoCEST agents.

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.

Copper(ii) complexes for cysteine detection using 19F magnetic resonance

Cysteine plays an essential role in maintaining cellular redox homeostasis and perturbations in cysteine concentration are associated with cardiovascular disease, liver disease, and cancer. 19F MRI is a promising modality for detecting cysteine in biology due to its high tissue penetration and negligible biological background signal. Herein we report fluorinated macrocyclic copper complexes that display a 19F NMR/MRI turn-on response following reduction of the Cu(ii) complexes by cysteine. The reactivity with cysteine was studied by monitoring the appearance of a robust diamagnetic 19F signal following addition of cysteine in conjunction with UV-vis and EPR spectroscopies. Importantly, complexes with-CH2CF3 tags display good water solubility. Studies with this complex in HeLa cells demonstrate the applicability of these probes to detect cysteine in complex biological environments.

Structural features of neutral and cationic cyclams

Dicationic compounds of general formula [1,8-R2-1,4,8,11-tetraazatricyclo[9.3.1.14,8]hexadecane]X2, where R = H, Me or Bn' and X is a halogen counterion were obtained by reactions of 1,4,8,11-tetraazatricyclo[9.3.1.14,8]hexadecane with different electrophiles. The solid-state molecular structures of the compounds reveal that the hydrogen, methyl or benzyl groups are located on the nitrogen atoms that are not only the less sterically hindered but also have the electron lone pair pointing out of the macrocycle backbone. In all compounds it is observed a bond shortening between the N-Caminal and the two other C-N bonds that may be attributed to an inductive effect. These compounds afford the corresponding trans-N,N'-disubstituted cyclams upon hydrolysis in basic medium.

NOVEL TETRA-AZA MACROCYCLIC COMPOUND, METHOD FOR PREPARING SAME, AND USE THEREOF

Provided are a cross-bridged tetraaza macrocyclic compound of a novel structure that can be used, for example, as a contrast agent for diagnostic imaging or a radiopharmaceutical and a method for preparing the same. The disclosed tetraaza macrocyclic comp

NOVEL TETRAAZA MACROCYCLIC COMPOUND, PREPARATION METHOD THEREOF AND USE THEREOF

Provided are a cross-bridged tetraaza macrocyclic compound of a novel structure that can be used, for example, as a contrast agent for diagnostic imaging or a radiopharmaceutical and a method for preparing the same. The disclosed tetraaza macrocyclic compound is able to form a stable metal complex at a lower temperature and allows easy conjugation with a bioactive substance or a chemically active substance, when compared to the existing cross-bridged tetraaza macrocyclic compounds.

From new tricyclic bisaminal derivatives to trans-N,N′-disubstituted cyclams

The reactivity of cyclam towards different aldehydes is discussed and the new tricyclic bisaminal derivatives thus obtained are characterized by X-ray crystallography; a new synthesis of trans-dibenzylcyclam is also reported.

Crystal structures and reactivity of 3a,5a,8a,10a-tetraazaperhydropyrene derivatives. An alternative approach to selective nitrogen alkylation of 1,4,8,11-tetraazacyclotetradecane (cyclam)

1-Alkyl and 1,8-dialkyl-1,4,8,11-tetraazacyclotetradecanes (alkyl = benzyl or methyl) were synthesised through cis-aminal of cyclam which was obtained by reaction of glyoxal and cyclam. The corresponding trans-aminal was synthesised from the respective li

New synthesis of trans-disubstituted cyclam macrocycles - Elucidation of the disubstitution mechanism on the basis of x-ray data and molecular modeling

A new way to synthesize trans-disubstituted cyclam tetraazamacrocycles 1 is reported. The synthesis proceeds in three steps via the tricyclic 1,4,8,11-tetraazatricyclo-[9.3.1.14,8]hexadecane system 2, which can be selectively dialkylated and hydrolyzed under basic conditions to give the final product 1. An understanding of the reactivity, based on the X-ray experimental electrostatic potential and molecular modeling of the 1,4,8,11-tetraazatricyclo-[9.3.1.14,8]hexadecane macrotricycle, has permitted the elucidation of a new reaction pathway leading to the trans-disubstituted cyclam.