55536-65-7

Basic information

• Product Name: 2-(3,4-bis(benzyloxy)phenyl)ethanamine
• Synonyms: 2-(3,4-bis(benzyloxy)phenyl)ethanamine
• CAS NO: 55536-65-7
• Molecular Weight: 333.43
• Mol File: 55536-65-7.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 2-(3,4-bis(benzyloxy)phenyl)ethanamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,4-bis(benzyloxy)phenyl)ethanamine(55536-65-7)
• EPA Substance Registry System: 2-(3,4-bis(benzyloxy)phenyl)ethanamine(55536-65-7)

Safety Data

• Hazardous Substances Data: 55536-65-7(Hazardous Substances Data)

Usage

General Description

2-(3,4-bis(benzyloxy)phenyl)ethanamine, also known as bis(benzyloxy)phenylethylamine, is a chemical compound with the molecular formula C26H27NO2. It is an amine derivative that is used in organic synthesis and pharmaceutical research. 2-(3,4-bis(benzyloxy)phenyl)ethanamine has two benzyl ether groups attached to a phenyl ring, and an ethanamine functional group. It can be used as a precursor in the synthesis of various drug candidates and organic molecules due to its versatile reactivity and functional groups. Its unique structure and properties make it a valuable building block in the field of organic chemistry and drug discovery.

Upstream product

• 51-61-6 dopamine 
• 100-44-7 benzyl chloride 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 5447-02-9 3,4-dibenzyloxybenzaldehyde 
• 62-31-7 dopamine hydrochloride 
• 37034-31-4 N-(tert-butoxycarbonyl)dopamine 
• 1699-54-3 3,4-bis(benzyloxy)-β-nitrostyrene 
• 1699-54-3 (E)-3,4-dibenzyloxy-β-nitrostyrene 
• 854882-14-7 (3,4-bis-benzyloxy-phenethyl)-carbamic acid methyl ester 
• 100-39-0 benzyl bromide 
• 42600-74-8 N-(3,4-dihydroxyphenethyl)pivalamide 

Downstream Products

• 72943-38-5 N-<<3,4-(dibenzyloxy)phenyl>ethyl>-2',4',5'-trimethoxyphenylacetamide 
• 37481-62-2 N-<3,4-bis(benzyloxy)phenylethyl>-3,4,5-trimethoxyphenylacetamide 
• 185104-75-0 N-[2-(3,4-Bis-benzyloxy-phenyl)-ethyl]-2-(4-hydroxy-3-nitro-phenyl)-acetamide 
• 566905-69-9 2,3,4,6-tetra-O-benzyl-1-O-[N-(3,4-dibenzyloxyphenylethyl)aminocarbonyl]-α-D-glucopyranose 
• 566905-68-8 benzyl 2,4,6-tri-O-benzyl-3-O-[N-(3,4-dibenzyloxyphenylethyl)aminocarbonyl]-β-D-glucopyranoside 
• 566905-64-4 benzyl 2,3,4-tri-O-benzyl-6-O-[N-(3,4-dibenzyloxyphenylethyl)aminocarbonyl]-β-D-glucopyranoside 
• 300362-70-3 3-(3,4-bis(benzyloxy)phenethylcarbamoyl) propanoic acid 
• 740083-57-2 tetrabenzyl 3-oxo-3-[2-(3,4-dibenzyloxyphenyl)ethylamino]propane-1,1-bisphosphonate 
• 248930-24-7 (2RS,3R)-3-amino-N-(3,4-bis(benzyloxy)phenethyl)-4-cyclohexyl-2-hydroxybutanamide hydrochloride 
• 1470017-24-3 N-(3,4-dibenzyloxyphenylethyl)-β-(3'-methoxyphenyl)acetamide 
• 1470017-26-5 C₃₁H₃₁NO₃ 
• 71201-34-8 7-{3-[2-(3,4-dihydroxyphenyl)-ethylamino]-butyl}-theophylline 
• 606977-99-5 2-biphenyl-4-yl-N-[2-(3,4-bis-benzyloxy-phenyl)-ethyl]-acetamide 
• 131946-64-0 1-<2-(4-benzyloxyphenyl)ethyl>-6,7-dibenzyloxy-1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

Hybrid hydrogels derived from renewable resources as a smart stimuli responsive soft material for drug delivery applications

The design and synthesis of amphiphilic molecules play a crucial role in fabricating smart functional materials via self-assembly. Especially, biologically significant natural molecules and their structural analogues have inspired chemists and made a majo

Designing new analogs for streamlining the structure of cytotoxic lamellarin natural products

Despite the therapeutic potential of marine-derived lamellarin natural products, their preclinical development has been hampered by their lipophilic nature, causing very poor aqueous solubility. In order to develop more drug-like analogs, their structure was streamlined in this study from both the cytotoxic activity and lipophilicity standpoints. First, a modified total synthetic route was successfully devised to construct a library of 59 systematically designed lamellarin analogs, which were then subjected to cytotoxicity and log P determinations. Along with the 25 first-generation lamellarins previously synthesized in our laboratory, the structure-activity and structure-lipophilicity relationships were extensively evaluated. Our results clearly indicated the additional structural requirements around the lamellarin skeleton which, when combined with those reported previously, can provide invaluable guidance for further modifications to increase the aqueous solubility of these compounds.

2,3,9- and 2,3,11-Trisubstituted tetrahydroprotoberberines as D2 dopaminergic ligands

Dopamine-mediated neurotransmission plays an important role in relevant psychiatric and neurological disorders. Nowadays, there is an enormous interest in the development of new dopamine receptors (DR) acting drugs as potential new targets for the treatment of schizophrenia or Parkinson's disease. Previous studies have revealed that isoquinoline compounds such as tetrahydroisoquinolines (THIQs) and tetrahydroprotoberberines (THPBs) can behave as selective D2 dopaminergic alkaloids since they share structural similarities with dopamine. In the present study we have synthesized eleven 2,3,9- and 2,3,11-trisubstituted THPB compounds (six of them are described for the first time) and evaluated their potential dopaminergic activity. Binding studies on rat striatal membranes were used to evaluate their affinity and selectivity towards D1 and D2 DR and establish the structure-activity relationship (SAR) as dopaminergic agents. In general, all the tested THPBs with protected phenolic hydroxyls showed a lower affinity for D1 and D2 DR than their corresponding homologues with free hydroxyl groups. In previous studies in which dopaminergic affinity of 1-benzyl-THIQs (BTHIQs) was evaluated, the presence of a Cl into the A-ring resulted in increased affinity and selectivity towards D2 DR. This is in contrast with the current study since the existence of a chlorine atom into the A-ring of the THPBs caused increased affinity for D1 DR but dramatically reduced the selectivity for D2 DR. An OH group in position 9 of the THPB (9f) resulted in a higher affinity for DR than its homologue with an OH group in position 11 (9e) (250 fold for D2 DR). None of the compounds showed any cytotoxicity in freshly isolated human neutrophils. A molecular modelling study of three representative THPBs was carried out. The combination of MD simulations with DFT calculations provided a clear picture of the ligand binding interactions from a structural and energetic point of view. Therefore, it is likely that compound 9d (2,3,9-trihydroxy-THPB) behave as D2 DR agonist since serine residues cluster are crucial for agonist binding and receptor activation.