101717-72-0

Basic information

• Product Name: (E)-N,N-dimethyl-2-(4-styrylphenoxy)ethanamine
• Synonyms: (E)-N,N-dimethyl-2-(4-styrylphenoxy)ethanamine
• CAS NO: 101717-72-0
• Molecular Weight: 267.371
• Mol File: 101717-72-0.mol

Chemical Properties

• CAS DataBase Reference: (E)-N,N-dimethyl-2-(4-styrylphenoxy)ethanamine(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-N,N-dimethyl-2-(4-styrylphenoxy)ethanamine(101717-72-0)
• EPA Substance Registry System: (E)-N,N-dimethyl-2-(4-styrylphenoxy)ethanamine(101717-72-0)

Safety Data

• Hazardous Substances Data: 101717-72-0(Hazardous Substances Data)

Upstream product

• 3839-46-1 stilben-4-ol 
• 5407-04-5 3-(dimethylamino)propyl chloride hydrochloride 
• 6554-98-9 trans-4-Hydroxystilbene 
• 4584-46-7 (2-chloroethyl)dimethylamine hydrochloride 
• 107-99-3 2-(dimethylamino)ethyl chloride 

Downstream Products

• 114186-93-5 diethyl-methyl-(2-trans-stilben-4-yloxy-ethyl)-ammonium; methyl sulfate 
• 286454-80-6 tetradecanoic acid 4-[4-(2-dimethylamino-ethoxy)-phenyl]-3-hydroxy-4-(4-methoxymethoxy-phenyl)-3-phenyl-1-tetradecanoyloxymethyl-butyl ester 
• 286454-79-3 tetradecanoic acid 4-[4-(2-dimethylamino-ethoxy)-phenyl]-3-hydroxy-3,4-diphenyl-1-tetradecanoyloxymethyl-butyl ester 
• 286454-78-2 1-[4-(2-dimethylamino-ethoxy)-phenyl]-1-(4-methoxymethoxy-phenyl)-2-phenyl-pent-4-en-2-ol 
• 286454-82-8 2-[4-(2-dimethylamino-ethoxy)-phenyl]-2-(4-methoxymethoxy-phenyl)-1-phenyl-ethanone 
• 286454-77-1 1-[4-(2-dimethylamino-ethoxy)-phenyl]-1,2-diphenyl-pent-4-en-2-ol 
• 286454-81-7 2-[4-(2-dimethylamino-ethoxy)-phenyl]-1,2-diphenyl-ethanone 

Relevant articles and documents

Synthesis of lipidic tamoxifen

We describe a general method for elaboration of the ethyl sidechain of tamoxifen and its primary 4-hydroxy metabolite. Novel lipidic tamoxifen and a functionalized B-ring analog were synthesized from a common stilbene oxide intermediate for potential lipo

A genomic DNA reporter screen identifies squalene synthase inhibitors that act cooperatively with statins to upregulate the low-density lipoprotein receptor

Hypercholesterolemia remains one of the leading risk factors for the development of cardiovascular disease. Many large double-blind studies have demonstrated that lowering low-density lipoprotein (LDL) cholesterol using a statin can reduce the risk of having a cardiovascular event by approximately 30%. However, despite the success of statins, some patient populations are unable to lower their LDL cholesterol to meet the targeted lipid levels, due to compliance or potency issues. This is especially true for patients with heterozygous familial hypercholesterolemia who may require additional upregulation of the low-density lipoprotein receptor (LDLR) to reduce LDL cholesterol levels below those achievable with maximal dosing of statins. Here we identify a series of small molecules from a genomic DNA reporter screen that upregulate the LDLR in mouse and human liver cell lines at nanomolar potencies (EC50 = 39 nM). Structure-activity relationship studies carried out on the lead compound, OX03771 [(E)-N,N-dimethyl-3-(4-styrylphenoxy)propan-1-amine], led to the identification of compound OX03050 [(E)-3-(4-styrylphenoxy)propan-1-ol], which had similar potency (EC50 = 26 nM) but a much-improved pharmacokinetic profile and showed in vivo efficacy. Compounds OX03050 and OX03771 were found to inhibit squalene synthase, the first committed step in cholesterol biosynthesis. These squalene synthase inhibitors were shown to act cooperatively with statins to increase LDLR expression in vitro. Overall, we demonstrated here a novel series of small molecules with the potential to be further developed to treat patients either alone or in combination with statins.