74447-33-9

Basic information

• Product Name: 1-(2'-azidoethyl)-4-(benzyloxy)benzene
• Synonyms: 1-(2'-azidoethyl)-4-(benzyloxy)benzene
• CAS NO: 74447-33-9
• Molecular Weight: 253.304
• Mol File: 74447-33-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-(2'-azidoethyl)-4-(benzyloxy)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2'-azidoethyl)-4-(benzyloxy)benzene(74447-33-9)
• EPA Substance Registry System: 1-(2'-azidoethyl)-4-(benzyloxy)benzene(74447-33-9)

Safety Data

• Hazardous Substances Data: 74447-33-9(Hazardous Substances Data)

Upstream product

• 86587-62-4 2-(4'-benzyloxy)phenethyl-p-methylbenzenesulfonate 
• 74447-35-1 1-azido-2-(4-methylsulphonyloxyphenyl)ethane 
• 100-44-7 benzyl chloride 
• 74447-34-0 1-azido-2-(4-hydroxyphenyl)ethane 

Downstream Products

• 501-94-0 p-hydroxyphenethyl alcohol 
• 74447-32-8 O,O-dibenzoyltyrosol 
• 60-19-5 tyramine hydrochloride 
• 51179-05-6 2-(4-(benzyloxy)phenyl)ethanamine 
• 2982-54-9 2-[4-(benzyloxy)phenyl]ethylamine hydrochloride 

Relevant articles and documents

Tacrine-O-protected phenolics heterodimers as multitarget-directed ligands against Alzheimer's disease: Selective subnanomolar BuChE inhibitors

Concerned by the devastating effects of Alzheimer's disease, and the lack of effective drugs, we have carried out the design of a series of tacrine-phenolic heterodimers in order to tackle the multifactorial nature of the disease. Hybridization of both pharmacophores involved the modification of the nature (imino, amino, ether) and the length of the tether, together with the type (hydroxy, methoxy, benzyloxy), number and position of the substituents on the aromatic residue. Title compounds were found to be strong and selective inhibitors of human BuChE (from low nanomolar to subnanomolar range), an enzyme that becomes crucial in the more advanced stages of the disease. The lead compound, bearing an ether-type tether, had an IC50 value of 0.52 nM against human BuChE, and a selectivity index of 323, with an 85-fold increase of activity compared to parent tacrine; key interactions were analysed using molecular modelling. Moreover, it also inhibited the self-aggregation of Aβ42, lacking neurotoxicity up to 5 μM concentration, and showed neuroprotective activity in primary rat neurons in a serum and K+ deprivation model, widely employed for reproducing neuronal injury and senescence. Moreover, low hepatoxicity effects and complete stability under physiological conditions were found for that compound. So, overall, our lead compound can be considered as a promising multitarget-directed ligand against Alzheimer's disease, and a good candidate for developing new drugs.

Studies of enzyme-mediated reactions. Part 12. Stereochemical course of the decarboxylation of (2S)-tyrosine to tyramine by microbial, mammalian, and plant systems.

-