452-15-3

Usage

Uses

Used in Pharmaceutical Industry:
N-(3-fluoro-4-Methoxyphenyl)acetaMide is used as a key intermediate for the synthesis of various therapeutic agents, particularly analgesic and anti-inflammatory drugs. Its unique molecular structure and properties make it a valuable building block in the development of new pharmaceuticals.
Used in Medicinal Chemistry:
N-(3-fluoro-4-Methoxyphenyl)acetaMide is utilized in medicinal chemistry for the design and synthesis of novel compounds with improved biological activity and pharmacokinetics. The presence of fluoro and methoxy substituents in the molecule allows for fine-tuning of its properties, making it a versatile starting material for the development of innovative therapeutic agents.

InChI:InChI=1/C9H10FNO2/c1-6(12)11-7-3-4-9(13-2)8(10)5-7/h3-5H,1-2H3,(H,11,12)

Upstream product

• 455-93-6 2-fluoro-1-methoxy-4-nitrobenzene 
• 108-24-7 acetic anhydride 
• 366-99-4 3-fluoro-4-methoxyaniline 
• 321-28-8 1-fluoro-2-methoxybenzene 

Downstream Products

• 448-26-0 N-(5-fluoro-4-methoxy-2-nitrophenyl)acetamide 
• 2045-39-8 N-(3-fluoro-4-hydroxy-phenyl)acetamide 
• 251902-52-0 2-chloro-7-fluoro-6-methoxy-3-quinolinecarbaldehyde 
• 1025986-25-7 4-Amino-2-diethylaminomethyl-6-fluoro-phenol 
• 155020-43-2 3-<(diethylamino)methyl>-5-fluoro-4-hydroxyacetanilide 
• 446-20-8 5-fluoro-4-methoxy-2-nitroaniline 

Relevant academic research and scientific papers

High Turnover Pd/C Catalyst for Nitro Group Reductions in Water. One-Pot Sequences and Syntheses of Pharmaceutical Intermediates

Commercially available Pd/C can be used as a catalyst for nitro group reductions with only 0.4 mol % Pd loading. The reaction can be performed using either silane as a transfer hydrogenating agent or simply a hydrogen balloon (μ1 atm pressure). With this technology, a series of nitro compounds was reduced to the desired amines in high chemical yields. Both the catalyst and surfactant were recycled several times without loss of reactivity.

Radical Beckmann Rearrangement and Its Application in the Formal Total Synthesis of Antimalarial Natural Product Isocryptolepine via C-H Activation

The Beckmann rearrangement of ketoximes, mediated by ammonium persulfate-dimethyl sulfoxide as a reagent, has been achieved under neutral conditions. Based on the radical trapping and 18O-labeling experiments, the transformation follows a mechanism involving a radical pathway. The scope and generality of the developed protocol has been demonstrated by 19 examples. The developed protocol and Pd-catalyzed intramolecular double C-H activation were used as key steps in the formal total synthesis of antimalarial natural product isocryptolepine.

Benzimidazole compound, and preparation method, intermediate and application thereof

The invention discloses a benzimidazole compound, and a preparation method, an intermediate and an application thereof. The invention provides a benzimidazole compound A or a pharmaceutically-acceptable salt thereof, and also provides an application of th

SUBSTITUTED 6,7-DIALKOXY-3-ISOQUINOLINOL DERIVATIVES AS INHIBITORS OF PHOSPHODIESTERASE 10 (PDE10A)

The invention relates to compounds of the formula wherein R′, R1, through R7 and Ar are as defined herein. These compounds are useful as inhibitors of phosphodiesterase 10 (PDE10A) which are useful in treating central nervous system diseases such as psychosis and also in treating, for example, obesity, type II diabetes, metabolic syndrome, glucose intolerance, pain and ophthalmic diseases.

Pd-catalyzed ortho-selective oxidative coupling of halogenated acetanilides with acrylates

Coupling of different halogenated acetanilides with acrylates using Pd-catalyzed ortho-selective C-H bond activation is reported. The yields of coupled products are low to high depending on the substrate. In general, arenes with electron-rich substituents like methoxy and methyl groups gave higher yields of the coupled products. The presence of the halogen substituent did not interfere with the activation process under these conditions.

Positive allosteric modulators of the nicotinic acetylcholine receptor

The invention provides compounds of Formula I: These compounds may be in the form of pharmaceutical salts or compositions, may be in pure enantiomeric form or racemic mixtures, and are useful in pharmaceuticals used to treat diseases or conditions in which α7 nAChR is known to be involved.

New tetracyclic analogues of camptothecins, their preparation processes, their use as medicaments and the pharmaceutical compositions containing them

The invention relates to new tetracyclic analogues of camptothecin, their preparation processes, their use as medicaments and the pharmaceutical compositions containing them. Said analogues, which include in particular 3-hydroxy-3-(4-oxo-4,6-dihydroindoli

The Effect of Fluorine Substitution on the Metabolism and Antimalarial Activity of Amodiaquine

Amodiaquine (AQ) (2) is a 4-aminoquinoline antimalarial which causes adverse side effects such as agranulocytosis and liver damage.The observed drug toxicity is believed to be related to the formation of an electrophilic metabolite, amodiaquine imine (AQQI), which can bind to cellular macro-molecules and initiate hypersensitivity reactions. 5'-Fluoroamodiaquine (5'-FAQ, 3), 5',6'-difluoroamodiaquine (5',6'-DIFAQ, 4), 2',6'-difluoroamodiaquine (2',6'-DIFAQ, 5), 2',5',6'-trifluoroamodiaquine (2',5',6'-TRIFAQ, 6) and 4'-dehydroxy-4'-fluoroamodiaquine (4'-deOH-4'-FAQ, 7) have been synthesized to assess the effect of fluorine substitution on the oxidation potential, metabolism, and in vitro antimalarial activity of amodiaquine.The oxidation potentials were measured by cyclic voltammetry, and it was observed that substitution at the 2',6'- and 4'-positions (2',6'-DIFAQ and 4'-deOH'4'-FAQ) produced analogues with significantly higher oxidation potentials than the parent drug.Fluorine substitution at the 2',6'-positions and 4'-position also produced analogues that were more resistant to bioactivation.Thus 2',6'-DIFAQ and 4'-deOH-4'-FAQ produced thioether conjugates corresponding to 2.17percent (SD: +/-0.27percent) and 0percent of the dose compared with 11.87percent (SD: +/-1.31percent) of the dose for amodiaquine.In general the fluorinated analogues had similar in vitro antimalarial activity to amodiaquine against the chloroquine resistant K1 strain of Plasmodium falciparum and the chloroquine sensitive T9-96 strain of P. falciparum with the notable exception of 2',5',6'-TRIFAQ (6).The data presented indicate that fluorine substitution at the 2',6'-positions and replacement of the 4'-hydroxyl of amodiaquine with fluorine produces analogues ( 5 and 7) that maintain antimalarial efficacy in vitro and are more resistant to oxidation and hence less likely to form toxic quinone imine metabolites.

The effect of fluorine substitution on the physicochemical properties and the analgesic activity of paracetamol

The physicochemical properties and analgesic action of six fluorinated analogues of 4-hydroxyacetanilide (paracetamol) have been investigated. Fluorine substitution adjacent to the hydroxyl group increased lipophilicity and oxidation potential whilst substitution adjacent to the amide had little effect on lipophilicity but led to a greater increase in oxidation potential. Lack of coplanarity and conjugation of the amide group and aromatic ring was also apparent with the analogues that had fluorine in the 2 and 6 positions. Introduction of fluorine into the amide group of paracetamol increased the lipophilicity 4-fold and also increased the oxidation potential of paracetamol. ED50 values for analgesic activity in the phenylquinone-induced abdominal constriction test on male Swiss White mice showed that ring substitution by fluorine reduced activity, especially at the 2,6-positions. Introduction of fluorine into the amide group enhanced activity significantly. Correlation of the analgesic activity with the physicochemical properties indicated that conjugation (and planarity) of the amide group with the aromatic ring is essential for activity and that ease of oxidation may also be an important factor.

4-Methyl-5-(unsubstituted and substituted phenoxy)-6-methoxy-8-(aminoalkylamino)quinolines

Compounds of the class including 4-methyl-5-(unsubstituted and substitutedhenoxy)-6-methoxy-8-(aminoalkylamino)quinolines as the free bases and pharmaceutically acceptable acid amine salts are described. The compounds are highly effective antimalarial agents which possess, surprisingly, both tissue schizonticidal (radical curative) and blood schizonticidal (suppressive) activity. In addition, these drugs have significantly better therapeutics indices than primaquine which is the current tissue schizonticidal drug of choice. Primaquine possesses no useful blood schizonticidal activity at tolerated dose levels.