350035-53-9

Basic information

• Product Name: ETHYL 4-BROMO-3,5-DIHYDROXYBENZOATE
• Synonyms: ETHYL 4-BROMO-3,5-DIHYDROXYBENZOATE
• CAS NO: 350035-53-9
• Molecular Formula: C₉H₉BrO₄
• Molecular Weight: 261.06936
• Product Categories: Aromatic Esters
• Mol File: 350035-53-9.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ETHYL 4-BROMO-3,5-DIHYDROXYBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 4-BROMO-3,5-DIHYDROXYBENZOATE(350035-53-9)
• EPA Substance Registry System: ETHYL 4-BROMO-3,5-DIHYDROXYBENZOATE(350035-53-9)

Safety Data

• Hazardous Substances Data: 350035-53-9(Hazardous Substances Data)

Upstream product

• 64-17-5 ethanol 
• 16534-12-6 3,5-dihydroxy-4-bromobenzoic acid 

Downstream Products

• 350035-54-0 ethyl-4-bromo-3-hydroxy-5-butyloxy-benzoate 
• 692203-96-6 ethyl 4-bromo-3-hydroxy-5-(methoxymethoxy)benzoate 
• 692205-49-5 4-bromo-3,5-dihydroxybenzyl alcohol 
• 745026-69-1 ethyl 4-bromo-3,5-dimethoxybenzoate 
• 820958-22-3 ethyl 4-bromo-3-decyloxy-5-hydroxybenzoate 
• 797815-36-2 ethyl-4-bromo-3,5-bis(methoxymethyloxy)benzoate 
• 906457-90-7 3-benzyloxy-4-bromo-5-hydroxy-benzoic acid ethyl ester 
• 906457-91-8 3-benzyloxy-2-bromo-5-hydroxymethyl-phenol 
• 906457-93-0 (3-benzyloxy-2-bromo-5-formyl-phenoxy)-acetic acid tert-butyl ester 
• 906457-92-9 (3-benzyloxy-2-bromo-5-hydroxymethyl-phenoxy)-acetic acid tert-butyl ester 
• 906457-96-3 (6-benzyloxy-3',5'-dihydroxy-4-hydroxymethyl-biphenyl-2-yloxy)-acetic acid tert-butyl ester 
• 906457-94-1 [6-benzyloxy-3',5'-bis-(tert-butyl-dimethyl-silanyloxy)-4-formyl-biphenyl-2-yloxy]-acetic acid tert-butyl ester 
• 906457-95-2 [6-benzyloxy-3',5'-bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxymethyl-biphenyl-2-yloxy]-acetic acid tert-butyl ester 
• 906457-99-6 [6-benzyloxy-3',5'-bis-(3-benzyloxy-5-tert-butoxycarbonylmethoxy-benzyloxy)-4-bromomethyl-biphenyl-2-yloxy]-acetic acid tert-butyl ester 

Relevant articles and documents

Discovery of novel somatostatin receptor subtype 5 (SSTR5) antagonists: Pharmacological studies and design to improve pharmacokinetic profiles and human Ether-a-go-go-related gene (hERG) inhibition

Somatostatin (SST) is a peptide hormone comprising 14 or 28 amino acids that inhibits endocrine and exocrine secretion via five distinct G-protein-coupled receptors (SSTR1–5). SSTR5 has an important role in inhibiting the secretion of pancreatic and gastrointestinal hormones (e.g., insulin, GLP-1, PYY) through the binding of SSTs; hence, SSTR5 antagonists are expected to be novel anti-diabetic drugs. In the course of our lead generation program of SSTR5 antagonists, we have discovered a novel spiroazetidine derivative 3a. However, pharmacological evaluation of 3a revealed that it had to be administered at a high dose (100?mg/kg) to show a persistent glucose-lowering effect in an oral glucose tolerance test (OGTT). We therefore initiated an optimization study based on 3a aimed at improving the antagonistic activity and mean residence time (MRT), resulting in the identification of 2-cyclopropyl-5-methoxybiphenyl derivative 3k. However, 3k did not show a sufficient persistent glucose-lowering effect in an OGTT; moreover, hERG inhibition was observed. Hence, further optimization study of the biphenyl moiety of compound 3k, focused on improving the pharmacokinetic (PK) profile and hERG inhibition, was conducted. Consequently, the introduction of a chlorine atom at the 6-position on the biphenyl moiety addressed a putative metabolic soft spot and increased the dihedral angle of the biphenyl moiety, leading to the discovery of 3p with an improved PK profile and hERG inhibition. Furthermore, 3p successfully exhibited a persistent glucose-lowering effect in an OGTT at a dose of 3?mg/kg.

Role of Aromatic Interactions in Temperature-Sensitive Amphiphilic Supramolecular Assemblies

Aromatic interactions were found to greatly influence the temperature-dependent dynamic behavior within supramolecular assemblies. Using an amphiphilic dendron, we systematically changed the hydrophobic groups introducing increasing levels of aromaticity while keeping the hydrophilic part constant. We show that the supramolecular assemblies become less sensitive to temperature changes when aromatic interactions in the aggregate are increased. Conversely, the absence of aromaticity in the hydrophobic moieties produces temperature-sensitive aggregates. These results show that subtle molecular-level interactions can be utilized to control temperature-sensitive behavior in the nanoscale. These findings open up new design strategies to rationally tune the behavior of stimuli-responsive supramolecular assemblies on multiple spatiotemporal scales.

SPIRO AZETIDINE ISOXAZOLE DERIVATIVES AND THEIR USE AS SSTR5 ANTAGONISTS

Provided is a compound represented by the following formula (1) or a salt thereof, which has an SSTR5 antagonistic action: wherein each symbol has the same definition as in the specification.