441741-65-7

Basic information

• Product Name: 2-Propenoic acid, 3-[4-[[[2-(2-Methyl-1H-indol-3-yl)ethyl]aMino]Methyl]phenyl]-, Methyl ester, (2E)-
• Synonyms: 2-Propenoic acid, 3-[4-[[[2-(2-Methyl-1H-indol-3-yl)ethyl]aMino]Methyl]phenyl]-, Methyl ester, (2E)-;(2E)-3-[4-[[[2-(2-Methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2-propenoic acid methyl ester;methyl (E)-3-(4-(((2-(2-methyl-1H-indol-3-yl)ethyl)amino)methyl)phenyl)acrylate
• CAS NO: 441741-65-7
• Molecular Formula: C₂₂H₂₄N₂O₂
• Molecular Weight: 348.43816
• Mol File: 441741-65-7.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-Propenoic acid, 3-[4-[[[2-(2-Methyl-1H-indol-3-yl)ethyl]aMino]Methyl]phenyl]-, Methyl ester, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, 3-[4-[[[2-(2-Methyl-1H-indol-3-yl)ethyl]aMino]Methyl]phenyl]-, Methyl ester, (2E)-(441741-65-7)
• EPA Substance Registry System: 2-Propenoic acid, 3-[4-[[[2-(2-Methyl-1H-indol-3-yl)ethyl]aMino]Methyl]phenyl]-, Methyl ester, (2E)-(441741-65-7)

Safety Data

• Hazardous Substances Data: 441741-65-7(Hazardous Substances Data)

Usage

General Description

2-Propenoic acid, 3-[4-[[[2-(2-Methyl-1H-indol-3-yl)ethyl]aMino]Methyl]phenyl]-, Methyl ester, (2E)-, also known as 3-(4-((2-(2-Methylindol-3-yl)ethyl)amino)methyl)phenyl)prop-2-enoic acid methyl ester, is a chemical compound with the molecular formula C24H26N2O2. It is a methyl ester derivative of 3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-propenoic acid. 2-Propenoic acid, 3-[4-[[[2-(2-Methyl-1H-indol-3-yl)ethyl]aMino]Methyl]phenyl]-, Methyl ester, (2E)- is not only used as a chemical intermediate or for research purposes, but it also has potential pharmaceutical applications due to its structural properties and potential biological activities. However, its specific uses and potential effects on human health and the environment should be thoroughly evaluated and researched before any practical applications.

Upstream product

• 2731-06-8 2-methyltryptamine 
• 7560-50-1 methyl (2E)-3-(4-formylphenyl)acrylate 
• 1122-91-4 4-bromo-benzaldehyde 
• 58045-41-3 methyl 3‐(4‐formylphenyl)acrylate 
• 1067-74-9 Methyl diethylphosphonoacetate 
• 73291-09-5 4-chloromethylbenzaldehyde 
• 5891-21-4 5-chloro-2-pentanone 
• 100-63-0 phenylhydrazine 
• 731846-75-6 methyl (E)-3-(4-(chloromethyl)phenyl)acrylate 

Downstream Products

• 404950-80-7 panobinostat 
• 960058-93-9 (E)-3-(4-(((2-(2-methyl-1H-indol-3-yl)ethyl)amino)methyl)phenyl)acrylic acid 
• 441741-66-8 (E)-3-[4-[[2-(2-methyl-1H-indol-3-yl)ethylamino]methyl]phenyl]acrylic acid methyl ester hydrochloride 

Relevant articles and documents

Development and pre-clinical testing of a novel hypoxia-activated KDAC inhibitor

Tumor hypoxia is associated with therapy resistance and poor patient prognosis. Hypoxia-activated prodrugs, designed to selectively target hypoxic cells while sparing normal tissue, represent a promising treatment strategy. We report the pre-clinical efficacy of 1-methyl-2-nitroimidazole panobinostat (NI-Pano, CH-03), a novel bioreductive version of the clinically used lysine deacetylase inhibitor, panobinostat. NI-Pano was stable in normoxic (21% O2) conditions and underwent NADPH-CYP-mediated enzymatic bioreduction to release panobinostat in hypoxia (2). Treatment of cells grown in both 2D and 3D with NI-Pano increased acetylation of histone H3 at lysine 9, induced apoptosis, and decreased clonogenic survival. Importantly, NI-Pano exhibited growth delay effects as a single agent in tumor xenografts. Pharmacokinetic analysis confirmed the presence of sub-micromolar concentrations of panobinostat in hypoxic mouse xenografts, but not in circulating plasma or kidneys. Together, our pre-clinical results provide a strong mechanistic rationale for the clinical development of NI-Pano for selective targeting of hypoxic tumors.

A handkerchief compared to department he and its key intermediate for the preparation of (by machine translation)

The invention belongs to the field of drug synthesis, in particular to a handkerchief compared to department he and its key intermediate of the preparation method, the method to cheap 4 - halogenated methyl formaldehyde, 2 - a primary amine and phosphine acyl acetic acid methyl ester compound as raw material, in the same pot obtain key intermediate (E)- 3 - [4 - [[2 - (2 - methyl - 1 H - indole - 3 - 3 yl) ethylamine] methyl] phenyl] acrylic acid methyl ester, obtained by the reaction with hydroxylamine handkerchief compared to department he, the method not only raw materials are cheap and easily obtained, and the cost is low, and there are few reaction steps, high yield and purity, mild reaction conditions at the same time, the operation is simple, is easy for industrial production. (by machine translation)

An improved and efficient synthesis of panobinostat

An improved and efficient method for the synthesis of panobinostat was developed. The commercially available starting material 4-(chloromethyl)benzaldehyde was converted to (E)-methyl 3-[4-(chloromethyl)phenyl]acrylate via the Wittig-Horner reaction and was then directly condensed with 2-(2-methyl-1H-indol-3-yl)ethanamine to afford the key intermediate (E)-methyl 3-[4-({[2-(2-methyl-1H-indol- 3-yl)ethyl]amino}methyl)phenyl]acrylate in a one-pot synthesis reactor. Subsequently a nucleophilic substitution reaction was carried out smoothly to generate the desired compound. The key intermediate and target compound were characterised by HRMS, 1H NMR and 13C NMR. This procedure is operationally simple and would be more suitable for industrial production.