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Usage

Uses

Used in Pharmaceutical Industry:
3-(4-Fluorophenoxy)propionic acid is used as a reactant for the synthesis of 2,3-dihydro-6-fluoro-4H-1-benzopyran-4-one, which may have potential applications in the development of pharmaceutical compounds. The synthesis of such compounds could lead to the creation of new drugs with various therapeutic properties.
Used in Chemical Synthesis:
In the field of chemical synthesis, 3-(4-Fluorophenoxy)propionic acid serves as a valuable building block for the creation of more complex molecules. Its unique structure, which includes a fluorine atom and a phenoxy group, may impart specific reactivity or selectivity in chemical reactions, making it a useful component in the synthesis of a wide range of compounds.
Used in Research and Development:
3-(4-Fluorophenoxy)propionic acid may also be utilized in research and development settings, where it can be explored for its potential applications in various fields. Scientists and researchers can use 3-(4-Fluorophenoxy)propionic acid to study its properties, reactivity, and potential interactions with other molecules, which could lead to the discovery of new applications and uses.

Upstream product

• 107-94-8 chloropropionic acid 
• 371-41-5 4-Fluorophenol 
• 85169-02-4 3-(4-fluoro-phenoxy)propionitrile 
• 104413-57-2 3-(4-fluorophenoxy)-1-propanol 
• 590-92-1 3-Bromopropionic acid 
• 371-40-4 4-fluoroaniline 

Downstream Products

• 66892-34-0 6-fluoro-4-chromanone 
• 81098-60-4 Acenalin 
• 368424-43-5 1-[3-(4-fluoro-phenoxy)-propionyl]-3-methoxy-piperidin-4-one 
• 368424-42-4 3-(4-fluoro-phenoxy)-1-(3,4,4-trimethoxy-piperidin-1-yl)-propan-1-one 
• 368424-41-3 3-(4-fluoro-phenoxy)-1-(3-hydroxy-4,4-dimethoxy-piperidin-1-yl)-propan-1-one 
• 82070-01-7 6-fluorochroman 
• 1421435-11-1 2-[2-(6-fluorochroman-4-ylidene)hydrazinyl]-5-phenylthiazole 
• 223136-62-7 N-Acetyl-1-(3-(4-fluorophenoxy)propyl)-4-aminopiperidine 
• 143922-25-2 4-amino-1-(3-(4-fluorophenoxy)propyl)piperidine 
• 223136-61-6 O-(p-toluenesulfonyl)-3-(4-fluorophenoxy)propanol 
• 1093091-90-7 2-chloro-6-(4-{3-[(4-fluorophenyl)oxy]propanoyl}-1-piperazinyl)benzonitrile 
• 1093091-89-4 5-chloro-2-(4-{3-[(4-fluorophenyl)oxy]propanoyl}-1-piperazinyl)benzonitrile 
• 1093092-11-5 1-{3-[(4-fluorophenyl)oxy]propanoyl}piperazine 

Relevant academic research and scientific papers

Acid activated montmorillonite K-10 mediated intramolecular acylation: Simple and convenient synthesis of 4-chromanones

3-Aryloxyproionic acids undergo intramolecular cyclization in the presence of AA.Mont.K-10 in toluene under reflux for 30–45 min in good to excellent yields. Phenyl ring bearing various substituents at the ortho, meta, para positions undergo this cyclization reaction. This method involves simple work up and amenable for large scale preparations. The heterogeneous acid treated catalyst can be regenerated and used for up to three cycles with minimum loss of activity.

Synthesis, evaluation and in silico molecular modeling of pyrroyl-1,3,4-thiadiazole inhibitors of InhA

Enoyl acyl carrier protein reductase (ENR) is an essential type II fatty acid synthase (FAS-II) pathway enzyme that is an attractive target for designing novel antitubercular agents. Herein, we report sixty-eight novel pyrrolyl substituted aryloxy-1,3,4-thiadiazoles synthesized by three-step optimization processes. Three-dimensional quantitative structure-activity relationships (3D-QSAR) were established for pyrrolyl substituted aryloxy-1,3,4-thiadiazole series of InhA inhibitors using the comparative molecular field analysis (CoMFA). Docking analysis of the crystal structure of ENR performed by using Surflex-Dock in Sybyl-X 2.0 software indicates the occupation of pyrrolyl substituted aryloxy 1,3,4-thiadiazole into hydrophobic pocket of InhA enzyme. Based on docking and database alignment rules, two computational models were established to compare their statistical results. The analysis of 3D contour plots allowed us to investigate the effect of different substituent groups at different positions of the common scaffold. In vitro testing of ligands using biological assays substantiated the efficacy of ligands that were screened through in silico methods.

Synthesis and antifungal activity of some thiazole derivatives

A series of some thiazole derivatives were designed and synthesized. The structure of newly synthesized compounds was characterized by HRMS, 1H NMR and 13C NMR. The synthesized compounds were evaluated against ten species of fungi in vitro by agar cup plate and micro-titration methods, respectively. The results of antifungal screening reveal that among all the compounds screened three compounds showed moderate antifungal activity. The MIC value of 3 h against two fungal strains C. neoformans and C. albicas is 8 μg mL-1 respectively. The MIC value of 3i against two fungal strains C. neoformans and T. mentagrophytes is 8 μg mL-1 and 16 μg mL-1, respectively and 3a against T. mentagrophytes is 16 μg mL-1, the MIC of others are all beyond 32 μg mL-1.

Design and synthesis of HIV-1 protease inhibitors for a long-acting injectable drug application

The design and synthesis of novel HIV-1 protease inhibitors (PIs) (1-22), which display high potency against HIV-1 wild-type and multi-PI-resistant HIV-mutant clinical isolates, is described. Lead optimization was initiated from compound 1, a Phe-Phe hydroxyethylene peptidomimetic PI, and was directed towards the discovery of new PIs suitable for a long-acting (LA) injectable drug application. Introducing a heterocyclic 6-methoxy-3-pyridinyl or a 6-(dimethylamino)-3-pyridinyl moiety (R3) at the para-position of the P1′ benzyl fragment generated compounds with antiviral potency in the low single digit nanomolar range. Halogenation or alkylation of the metabolic hot spots on the various aromatic rings resulted in PIs with high stability against degradation in human liver microsomes and low plasma clearance in rats. Replacing the chromanolamine moiety (R1) in the P2 protease binding site by a cyclopentanolamine or a cyclohexanolamine derivative provided a series of high clearance PIs (16-22) with EC50s on wild-type HIV-1 in the range of 0.8-1.8 nM. PIs 18 and 22, formulated as nanosuspensions, showed gradual but sustained and complete release from the injection site over two months in rats, and were therefore identified as interesting candidates for a LA injectable drug application for treating HIV/AIDS.

Novel thiazolidine derivatives

The invention relates to with novel thiazolidine derivatives of the formula STR1 wherein X is methylene, oxygen or sulfur; R1 is halogen; R2 is hydrogen, nitro, cyano, OR3 or NHR3 ; or R1 and R2 both simultaneously are hydrogen or nitro; R3 is hydrogen, alkyl, acyl, --CO--OR4 or --CO--NHR4 ; and R4 is alkyl, unsubstituted or substituted aryl or aralkyl, and their salts with physiologically compatible cations. The compounds of formula I are useful in the treatment of metabolic disorders.

Process for preparing 6-fluoro-4-chromanone using 3-(4-fluorophenoxy)propionitrile

The present invention relates to 3-(4-fluorophenoxy)propionitrile having the formula (I): STR1 a process for preparing 3-(4-fluorophenoxy)propionitrile having the formula (I) which comprises reacting 4-fluorophenol and acrylonitrile in the presence of a tertiary amine, a process for preparing 6-fluoro-4-chromanone having the formula (II): STR2 which comprises reacting 3-(4-fluorophenoxy)propionitrile having the formula (I) with an acid, and a process for preparing 6-fluoro-4-chromanone having the formula (II) which comprises reacting 4-fluorophenol with acrylonitrile in the presence of a catalyst to give 3-(4-fluorophenoxy)propionitrile having the formula (I), which is then reacted with an acid. 6-Fluoro-4-chromanone is an important intermediate for the synthesis of (S)-2,3-dihydro-6-fluoro-spiro[4H-1-benzopyran-4,4'-imidazolidine]-2',5'dione (USAN: sorbinil).