405-85-6

Usage

Uses

Used in Pharmaceutical Industry:
4-[(3-FLUOROBENZYL)OXY]BENZENECARBOXYLIC ACID is used as a metabolite in the treatment of Parkinson's disease for its role in the metabolism of Safinamide. Safinamide, as an add-on treatment, helps manage the symptoms of Parkinson's disease by inhibiting the enzyme MAO-B, which is responsible for the breakdown of dopamine in the brain. This inhibition leads to an increase in dopamine levels, thereby providing relief from the motor symptoms associated with the disease.

InChI:InChI=1/C14H11FO3/c15-12-3-1-2-10(8-12)9-18-13-6-4-11(5-7-13)14(16)17/h1-8H,9H2,(H,16,17)

Upstream product

• 454473-78-0 methyl 4-[(3-fluorobenzyl)oxy]benzoate 
• 456-41-7 1-(Bromomethyl)-3-fluorobenzene 
• 99-96-7 4-hydroxy-benzoic acid 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 456-42-8 m-fluorobenzyl chloride 

Downstream Products

• 1160250-86-1 C₁₄H₁₀ClFO₂ 

Relevant academic research and scientific papers

Design and biological evaluation of phenyl imidazole analogs as hedgehog signaling pathway inhibitors

The hedgehog (Hh) signaling pathway is involved in diverse aspects of cellular events. Aberrant activation of Hh signaling pathway drives oncogenic transformation for a wide range of cancers, and it is therefore a promising target in cancer therapy. In the principle of association and ring-opening, we designed and synthesized a series of Hh signaling pathway inhibitors with phenyl imidazole scaffold, which were biologically evaluated in Gli-Luc reporter assay. Compound 25 was identified to possess high potency with nanomolar IC50, and moreover, it preserved the inhibition against wild-type and drug-resistant Smo-overexpressing cells. A molecular modeling study of compound 25 expounded its binding mode to Smo receptor, providing a basis for the further structural modification of phenyl imidazole analogs.

Discovery of benzamide-hydroxypyridinone hybrids as potent multi-targeting agents for the treatment of Alzheimer's disease

A novel class of benzamide-hydroxypyridinone (HPO) derivatives were innovatively designed, synthesised, and biologically evaluated as potential multitargeting candidates for the treatment of Alzheimer's disease (AD) through pharmacophores-merged approaches based on lead compounds 18d, benzyloxy phenyl analogs, and deferiprone (DFP). These hybrids possessed potent Monoamine oxidase B (MAO-B) inhibition as well as excellent iron chelation, with pFe3+ values ranging from 18.13 to 19.39. Among all the compounds, 8g exhibited the most potent selective MAO-B inhibitor (IC50 = 68.4 nM, SI = 213). Moreover, 8g showed favourable pharmacokinetic properties and had great potential to penetrate the BBB in silico and PAMPA-BBB assay. Molecular modelling showed that 8g could adopt an extended conformation and have more enhanced interactions with MAO-B than 18d. In vitro and in vivo assays demonstrated that 8g remarkably resisted Aβ-induced oxidation and ameliorated cognitive impairment induced by scopolamine. Taken collectively, these results suggest that compound 8g is a potential multifunctional candidate for anti-AD treatment.

Formamide pyridone iron chelating agent derivative with potential multi-target anti-AD activity as well as preparation method and application thereof

The invention provides a formamide pyridone iron chelating agent derivative shown as a formula (I) or a formula (II) which is described in the specification and a preparation method and application thereof. The formamide pyridone iron chelating agent derivative shown in the formula (I) or the formula (II) and the pharmaceutically acceptable salt thereof have the effects of inhibiting monoamine oxidase, chelating metal iron ions, resisting A beta and resisting oxidation activity. The derivative can be used for preparing medicines for resisting Alzheimer's disease, Parkinson's disease or other diseases treated by inhibiting monoamine oxidase, chelating metal iron ions, resisting A beta and resisting oxidation.

Synthesis and evaluation of novel N-3-benzimidazolephenylbisamide derivatives for antiproliferative and Hedgehog pathway inhibitory activity

A series of novel N-3-benzimidazolephenylbisamide derivatives bearing the 4-benzyloxyphenyl moiety were synthesized and evaluated for their antiproliferative activity against MGC803, HT29, MKN45 and SW620 cancer cell lines in vitro. The pharmacological data demonstrated that the majority of the target compounds exhibited higher efficacy against MGC803, HT29 and MKN45 cells, among which compound 7m displayed higher antiproliferative activity than vismodegib. Furthermore, compound 7m manifested better inhibition of the Hedgehog (Hh) signaling pathway in different Hh-related assays and may compete with boron-dipyrromethene (BODIPY)-cyclopamine for binding to the human smoothened (Smo) receptor. In addition, molecular docking studies suggested that compound 7m interacts very closely with the vismodegib docking pose through hydrogen bonds at the taladegib binding site of the Smo receptor.