366-77-8

Basic information

• Product Name: 3-(4-FLUOROBENZOYL)PROPIONIC ACID
• Synonyms: HALOPERIDOL METABOLITE III;LABOTEST-BB LT00233221;3-(4'-FLUOROBENZOYL)PROPIONIC ACID;3-(4-FLUOROBENZOYL)PROPIONIC ACID;4-(4-FLUOROPHENYL)-4-OXOBUTANOIC ACID;4-(4-FLUOROPHENYL)-4-OXOBUTYRIC ACID;AKOS BBS-00006441;R 11302
• CAS NO: 366-77-8
• Molecular Formula: C₁₀H₉FO₃
• Molecular Weight: 196.18
• EINECS: 206-679-1
• Product Categories: Aromatic Propionic Acids;Acids & Esters;Fluorine Compounds;Aromatic Building Blocks
• Mol File: 366-77-8.mol
• Article Data: 43

Chemical Properties

• Melting Point: 100-102 °C(lit.)
• Boiling Point: 374.4 °C at 760 mmHg
• Flash Point: 180.3 °C
• Appearance: beige granular powder
• Density: 1.2441 (estimate)
• Vapor Pressure: 2.85E-06mmHg at 25°C
• Refractive Index: 1.528
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.50±0.17(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 958145
• CAS DataBase Reference: 3-(4-FLUOROBENZOYL)PROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-FLUOROBENZOYL)PROPIONIC ACID(366-77-8)
• EPA Substance Registry System: 3-(4-FLUOROBENZOYL)PROPIONIC ACID(366-77-8)

Safety Data

• Hazard Codes: Xn,C,Xi
• Statements: 36/37/38-20/21/22-22
• Safety Statements: 36/37/39-26-22-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 366-77-8(Hazardous Substances Data)

Usage

Uses

7-Fluoro-1-tetralone was prepared from 3-(4-fluorobenzoyl)-propionic acid by Wolff-Kishner reduction followed by ring closure with polyphosphoric acid and other substituted 1-tetralones where commercially available. Reduction of 3-(4-fluorobenzoyl)propionic acid with an excess of tert-butylamine borane (TBAB) in the presence of AlCl3 provided 4-(4-fluorophenyl)-1-butanol (87) in 63% yield for the synthesis of LM-1507 sodium salt. Penfluridol 1-[4,4-bis(4-fluorophenyl)butyl]-4-(4-chloro-3-trifluoromethylphenyl)- 4-hydroxypiperidine, C 28 H 27 ClF 5 NO, M r 523.99, mp 105 - 107°C, is obtained by reducing the ketone of 3-(4-fluorobenzoyl)propionic acid into a lactone.

General Description

3-(4-Fluorobenzoyl)propionic acid is a metabolite of haloperidol, a dopamine D2 receptor blocker.

InChI:InChI=1/C10H9FO3/c11-8-3-1-7(2-4-8)9(12)5-6-10(13)14/h1-4H,5-6H2,(H,13,14)

Upstream product

• 10457-90-6 bromperidol 
• 108-30-5 succinic acid anhydride 
• 352-13-6 4-flourophenylmagnesium bromide 
• 352-34-1 4-fluoro-1-iodobenzene 
• 462-06-6 fluorobenzene 
• 86798-58-5 α-<4-(1H-imidazol-1-yl)phenyl>-4-morpholineacetonitrile 
• 88427-81-0 4-(1H-imidazol-1-yl)-β-methyl-γ-oxobenzenebutanoic acid 

Downstream Products

• 41310-80-9 ethyl 4-(4-fluorophenyl)-4-oxobutanoate 
• 49780-08-7 β-bromo-β-p-fluorobenzoyl-propionic acid 
• 97150-72-6 4oxo-4(4-pyrazol-1-yl-phenyl)butyric acid 
• 86798-53-0 4-(4-hydroxymethyl-1H-imidazol-1-yl)-γ-oxobenzenebutanoic acid 
• 1026187-68-7 C₁₃H₁₃FO₅ 
• 148903-20-2 4-(4-Fluorphenylmethyl)-3-methylen-4,5-dihydro-2(3H)-furanon 
• 142720-24-9 N,N-dihexyl-2-(4-fluorophenyl)indole-3-acetamide 
• 142720-25-0 FGIN 1-45 
• 148133-91-9 trans-4-(4-Fluorphenylmethyl)-3-<4-(2-oxo-1-benzimidazolinyl)-piperidinomethyl>-4,5-dihydro-2(3H)-furanon 
• 148133-92-0 trans-3-<4-(4-Chlorphenyl)-4-hydroxy-piperidinomethyl>-4-(4-fluorphenylmethyl)-4,5-dihydro-2(3H)-furanon-hydrochlorid 
• 148133-89-5 cis/trans-4-(4-Fluorphenylmethyl)-3-(4-methylpiperidinomethyl)-4,5-dihydro-2(3H)-furanon-hydrochlorid 
• 133188-66-6 4-(4-fluorophenyl)butyryl chloride 
• 51787-96-3 5-(4-fluorophenyl)dihydrofuran-2(3H)-one 
• 36330-84-4 3-<4-(phenylthio)benzoyl>propionic acid 

Relevant articles and documents

Role of CYP3A in bromperidol metabolism in rat in vitro and in vivo

1. The aim was to identify whether CYP3A metabolizes bromperidol (BP), an antipsychotic drug, to form 4-fluorobenzoyl-propionic acid (FBPA) in hepatic microsomes from 8-week-old male Sprague-Dawley rats and to investigate whether an inhibitor or an inducer of CYP3A affects BP pharmacokinetics in rat. 2. In an in vitro study, only troleandomycin showed marked inhibition of FBPA formation among several specific CYP isozyme inhibitors studied including troleandomycin, diethyldithiocarbamate, furafylline and quinine. Anti-rat CYP3A2 serum inhibited FBPA formation by 80%, whereas other anti-rat CYP sera (1A1, 1A2, 2B1, 2C11, 2E1) only slightly inhibited it. 3. In a pharmacokinetic study, BP half-life was prolonged to 137% of the average control value by 7-day treatment with erythromycin, a CYP3A inhibitor, and shortened to 58% of the control by 2-day treatment with dexamethasone, a CYP3A inducer. BP clearance was reduced to 68% of the control by erythromycin and was increased to 145% of control by dexamethasone. 4. These results suggested that BP biotransformation is catalysed mainly by CYP3A to form FBPA in rat and that the modification of this enzyme activity would affect the pharmacokinetics of BP.

Method for synthesizing 4-(4-fluorobenzoyl) butyric acid and analogues thereof in continuous flow microreactor

The invention relates to a method for synthesizing 4-(4-fluorobenzoyl) butyric acid and analogues thereof in a continuous flow microreactor, which comprises the following steps: (1) uniformly mixing a compound 1 and a compound 2 to obtain a homogeneous phase solution A; (2) uniformly mixing aluminum trichloride, a compound 1 and an organic solvent to obtain a homogeneous phase solution B; (3) diluting concentrated hydrochloric acid with water to prepare a solution C; and (4) transferring the homogeneous phase solution A and the homogeneous phase solution B into a first micro-reaction module for a Friedel-Crafts acylation reaction, after the reaction is finished, transferring the obtained reaction solution and the solution C into a second micro-reaction module for quenching reaction, and then performing liquid separation, washing and vacuum concentration to obtain a target compound 3; wherein the specific synthesis route is as follows. By adopting the method disclosed by the invention, the target product can be continuously and rapidly synthesized, aluminum trichloride is not needed for treatment, the reaction condition is mild, the reaction time is short, and the yield is high and reaches 90% or above.

In silico designing, in vitro and in vivo evaluation of potential PPAR-γ agonists derived from aryl propionic acid scaffold

Attributed to several side effects, especially on hepatic tissues and body weight, there is always an urge of innovation and upgrading in already existing medication being used in maintaining diabetic condition. Therefore, in the present work, forty-eight molecules derived from arylpropionic acid scaffold were synthesized and their evaluation against diabetes was carried out. The synthesis of these molecules attributed to excellent dock score displayed by all the structures performed against PPAR-γ receptor site. Subsequently, all the derivatives were primarily deduced for their antidiabetic potential by OGTT. The compounds that showed significant antidiabetic activity in OGT Test and also exhibited high dock scores were assessed further by in vitro PPAR transactivation assay to assure analogy between in vivo and in vitro studies. The antidiabetic activity of these active compounds was then evaluated on STZ induced diabetic model in vivo. The most active compounds were scrutinized for its effect on PPAR-γ gene expression and hepatotoxic effect. Finally, it was recapitulated that these derivatives can provide a new prospect towards the development of antidiabetic agents with fewer side effects.

A class of histone acetylase p300 inhibitors, and application thereof

The invention discloses a class of histone acetylase p300 inhibitors, and application thereof, and belongs to the technical field of medicinal chemistry. The invention discloses a compound representedby a formula (I), or a stereochemical isomer, a solvate or a pharmaceutically acceptable salt thereof. According to the invention, the compound can effectively inhibit the activity of histone acetylase p300 and can effectively inhibit the proliferation activity of various tumor cells; the compound is combined with a CDK4/6 inhibitor to play a synergistic role in inhibiting proliferation of tumorcells; and the compound has good application prospects in preparation of histone acetylase inhibitors, preparation of drugs for preventing and/or treating cancers, metabolic diseases, neurological diseases or inflammations, and combination of drugs.