444807-46-9

Basic information

• Product Name: METHYL 4-AMINOMETHYLPHENYLACETATE
• Synonyms: METHYL 4-AMINOMETHYLPHENYLACETATE;Methyl 4-aminomethylphenylacetate HCl;Methyl 4-aminomethylphenylacetate hydrochloride;Benzeneacetic acid, 4-(aMinoMethyl)-, Methyl ester;methyl 2-(4-(aminomethyl)phenyl)acetate
• CAS NO: 444807-46-9
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 179.22
• Product Categories: pharmacetical
• Mol File: 444807-46-9.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 315.7°Cat760mmHg
• Flash Point: 144.7°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 0.000316mmHg at 25°C
• CAS DataBase Reference: METHYL 4-AMINOMETHYLPHENYLACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 4-AMINOMETHYLPHENYLACETATE(444807-46-9)
• EPA Substance Registry System: METHYL 4-AMINOMETHYLPHENYLACETATE(444807-46-9)

Safety Data

• Hazardous Substances Data: 444807-46-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H13NO2.ClH/c1-13-10(12)6-8-2-4-9(7-11)5-3-8;/h2-5H,6-7,11H2,1H3;1H

Upstream product

• 67-56-1 methanol 
• 1200-05-1 2-(4-(aminomethyl)phenyl)acetic acid 
• 52798-01-3 methyl 4-cyanobenzeneacetate 
• 41841-16-1 (4-bromo-phenyl)-acetic acid methyl ester 
• 1878-68-8 2-(4-bromophenyl)-acetic acid 
• 13737-36-5 4-bromophenylacetic acid 
• 7398-42-7 methyl 2-(4-(bromomethyl)phenyl)acetate 
• 5462-71-5 4-cyanophenylacetic acid 

Downstream Products

• 808753-33-5 [4-(thiophene-2-sulfonylamino-methyl)-phenyl]-acetic acid methyl ester 
• 808753-26-6 [4-(propane-2-sulfonylamino-methyl)-phenyl]-acetic acid methyl ester 
• 808753-27-7 [4-(propane-1-sulfonylamino-methyl)-phenyl]-acetic acid methyl ester 
• 808753-28-8 [4-(butane-1-sulfonylamino-methyl)-phenyl]-acetic acid methyl ester 
• 191871-32-6 [4-(tert-butoxycarbonylamino-methyl)-phenyl]-acetic acid methyl ester 
• 808753-30-2 [4-(4-fluoro-benzenesulfonylamino-methyl)-phenyl]-acetic acid methyl ester 
• 808753-03-9 [4-(methanesulfonylamino-methyl)-phenyl]-acetic acid methyl ester 
• 808753-29-9 methyl 2-(4-(phenylsulfonamidomethyl)phenyl)acetate 
• 808753-31-3 [4-(toluene-4-sulfonylamino-methyl)-phenyl]-acetic acid methyl ester 
• 808753-25-5 [4-(ethanesulfonylamino-methyl)-phenyl]-acetic acid methyl ester 
• 808753-32-4 [4-(phenyl-methanesulfonylamino-methyl)-phenyl]-acetic acid methyl ester 
• 110626-68-1 2-(4-(methanesulfonoamidomethyl)phenyl)acetic acid 
• 808753-35-7 [4-(ethanesulfonylamino-methyl)-phenyl]-acetic acid 
• 808753-36-8 [4-(propane-2-sulfonylamino-methyl)-phenyl]-acetic acid 

Relevant articles and documents

Discovery of carboxyl-containing biaryl ureas as potent RORγt inverse agonists

GSK805 (1) is a potent RORγt inverse agonist, but a drawback of 1 is its low solubility, leading to a limited absorption in high doses. We have explored detailed structure-activity relationship on the amide linker, biaryl and arylsulfonyl moieties of 1 trying to improve solubility while maintaining RORγt activity. As a result, a novel series of carboxyl-containing biaryl urea derivatives was discovered as potent RORγt inverse agonists with improved drug-like properties. Compound 3i showed potent RORγt inhibitory activity and subtype selectivity with an IC50 of 63.8 nM in RORγ FRET assay and 85 nM in cell-based RORγ-GAL4 promotor reporter assay. Reasonable inhibitory activity of 3i was also achieved in mouse Th17 cell differentiation assay (76percent inhibition at 0.3 μM). Moreover, 3i had greatly improved aqueous solubility at pH 7.4 compared to 1, exhibited decent mouse PK profile and demonstrated some in vivo efficacy in an imiquimod-induced psoriasis mice model.

BIARYL COMPOUND, PREPARATION METHOD AND USE THEREFOR

The present invention belongs to the technical field of chemical pharmaceuticals, and relates to a compound represented by general formula (I) or formula (II) and a preparation method thereof. The compounds are biaryl derivatives with RORγt activation activity. The biaryl derivatives disclosed in this invention can effectively activate the RORγt protein receptor, and thereby promote the differentiation of Th17 cells and increasing the production of IL-17, which can be used as an immune modulator for the treatment of various cancers or viral infection-related diseases.

A Dual Modulator of Farnesoid X Receptor and Soluble Epoxide Hydrolase to Counter Nonalcoholic Steatohepatitis

Nonalcoholic steatohepatitis arising from Western diet and lifestyle is characterized by accumulation of fat in liver causing inflammation and fibrosis. It evolves as serious health burden with alarming incidence, but there is no satisfying pharmacological therapy to date. Considering the disease's multifactorial nature, modulation of multiple targets might provide superior therapeutic efficacy. In particular, farnesoid X receptor (FXR) activation that revealed antisteatotic and antifibrotic effects in clinical trials combined with inhibition of soluble epoxide hydrolase (sEH) as anti-inflammatory strategy promises synergies. To exploit this dual concept, we developed agents exerting partial FXR agonism and sEH inhibitory activity. Merging known pharmacophores and systematic exploration of the structure-activity relationship on both targets produced dual modulators with low nanomolar potency. Extensive in vitro characterization confirmed high dual efficacy in cellular context combined with low toxicity, and pilot in vivo data revealed favorable pharmacokinetics as well as engagement on both targets in vivo.