2713-85-1

Usage

Uses

Used in Pharmaceutical Industry:
N-(4-FLUORO-PHENYL)-3-OXO-BUTYRAMIDE is used as a key intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs with improved therapeutic properties. Its unique structure allows for the creation of compounds with enhanced bioavailability, selectivity, and efficacy.
Used in Agrochemical Industry:
In the agrochemical sector, N-(4-FLUORO-PHENYL)-3-OXO-BUTYRAMIDE is utilized as a precursor in the production of agrochemicals, such as pesticides and herbicides. Its incorporation into these products can lead to more effective and targeted pest control solutions.
Used in Organic Compounds Synthesis:
N-(4-FLUORO-PHENYL)-3-OXO-BUTYRAMIDE is used as a building block in the synthesis of a range of organic compounds, enabling the creation of novel molecules with diverse applications across various industries.
Used in Medicinal Chemistry Research and Development:
N-(4-FLUORO-PHENYL)-3-OXO-BUTYRAMIDE serves as a valuable tool in medicinal chemistry, where it is employed in the design and synthesis of biologically active molecules. Its potential pharmacological activities make it a promising candidate for further research and development in drug discovery processes.
Used in Drug Discovery:
N-(4-FLUORO-PHENYL)-3-OXO-BUTYRAMIDE is utilized in drug discovery efforts to identify and optimize new lead compounds with therapeutic potential. Its unique structural features facilitate the exploration of novel chemical space and the development of innovative therapeutic agents.

InChI:InChI=1/C10H10FNO2/c1-7(13)6-10(14)12-9-4-2-8(11)3-5-9/h2-5H,6H2,1H3,(H,12,14)

Upstream product

• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 371-40-4 4-fluoroaniline 
• 105-45-3 acetoacetic acid methyl ester 
• 141-97-9 ethyl acetoacetate 
• 674-82-8 4-methyleneoxetan-2-one 

Downstream Products

• 537678-50-5 C₁₈H₁₅FN₄O₄ 
• 537678-81-2 C₁₈H₁₅ClFN₃O₂ 
• 400024-07-9 4-bromo-N-(4-fluorophenyl)-3-oxobutanamide 
• 1258407-70-3 4-(furan-2-yl)-6-methyl-N-(4-fluorophenyl)-4,7-dihydro-2H-pyrazolo[3,4-b]pyridine-5-carboxamide 
• 1258407-60-1 4-phenyl-6-methyl-N-(4-fluorophenyl)-4,7-dihydro-2H-pyrazolo[3,4-b]pyridine-5-carboxamide 
• 1057675-61-2 N-(4-fluorophenyl)-2-hydroxyimino-3-oxobutyramide 
• 1256814-15-9 N-(p-fluorophenyl)-1,5-dimethyl-3-oxido-1H-imidazole-4-carboxamide 
• 1282423-35-1 C₂₇H₂₁ClFN₅OS 
• 1282423-16-8 C₂₇H₂₁ClFN₅O₂ 
• 1608483-65-3 8-bromo-2-(4-fluorophenyl)-4-methyl-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione 
• 1608483-69-7 8-chloro-2-(4-fluorophenyl)-4-methyl-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione 
• 687573-42-8 2-(4-fluorophenyl)-4-methyl-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione 
• 18529-12-9 2-chloro-6-fluoro-4-methylquinoline 
• 607-40-9 6-fluoro-2-hydroxy-quinoline-4-carboxylic acid 

Relevant academic research and scientific papers

Structural motifs in acetoacetanilides: The effect of a fluorine substituent

The structures of three fluoro-substituted acetoacetanilides were discussed. A planar structure with intramolecular hydrogen bonding was observed when the F atom was in ortho position of the aromatic ring, and a twisted structure with intermolecular hydrogen bonding was observed when the F atom was in meta or para positions. Fluorine appeared to mimic the steric effect of a large substituent which was attributed to high electronegativity.

Visible Light-Induced Pericyclic Cascade Reaction for the Synthesis of Quinolinone Derivatives with an Oxabicyclo[4.2.0]octene Skeleton

A photoinduced pericyclic cascade reaction has been developed to afford oxabicyclo[4.2.0]octenes. Mechanistic studies show that this reaction undergoes [2 + 2]-photocycloaddition, base-promoted elimination, retro-4π-electrocyclization, [1,5]-H shift, and

Ru-NHC-Catalyzed Asymmetric Hydrogenation of 2-Quinolones to Chiral 3,4-Dihydro-2-Quinolones

Direct enantioselective hydrogenation of unsaturated compounds to generate chiral three-dimensional motifs is one of the most straightforward and important approaches in synthetic chemistry. We realized the Ru(II)-NHC-catalyzed asymmetric hydrogenation of 2-quinolones under mild reaction conditions. Alkyl-, aryl- and halogen-substituted optically active dihydro-2-quinolones were obtained in high yields with moderate to excellent enantioselectivities. The reaction provides an efficient and atom-economic pathway to construct simple chiral 3,4-dihydro-2-quinolones. The desired products could be further reduced to tetrahydroquinolines and octahydroquinolones.

Synthesis and in vitro Antidiabetic Screening of Novel Dihydropyrimidine Derivatives

Abstract: A series of N-substituted-6-methyl-4-{4-[5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl]methoxyphenyl}-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamides have been synthesized by the condensation of newly synthesized {4-[5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl]methoxy}benzaldehyde with variously substituted acetoacetanilides and urea in the presence of ethanol. The synthesized compounds have been characterized by 1H, 13C NMR, IR spectroscopy, and mass spectrometry. All synthesized compounds were evaluated for in vitro antidiabetic activity using the α-amylase inhibition assay with the 3,5-dinitrosalicylic acid (DNSA) reagent.

Palladium-Catalyzed Regioselective Coupling Cyclohexenone into Indoles: Atom-Economic Synthesis of β-Indolyl Cyclohexenones and Derivatization Applications

Herein, we report a palladium-catalyzed dehydrogenative cross-coupling of indoles with cyclic enones to give β-indolyl cyclic enones under mild and neutral reaction conditions. The key to the success is to explore a mild condition, which ensures the indole C-H activation and subsequent syn β-hydride elimination through rapid enolization isomerization of Pd(II)-enolate while suppressing other undesired side reactions. Synthetic utility has also been demonstrated in the flexible transformation of the coupling products to meta-phenols and benzo[a]carbazoles.

Phenothiazine and amide-ornamented novel nitrogen heterocyclic hybrids: synthesis, biological and molecular docking studies

The synthesis of novel hybrids, namely, phenothiazine and amide-ornamented nitrogen heterocycles (25-34) has been accomplished utilizing a multi-step synthetic protocol and the structures have been established based on physical and spectral techniques. Of these, the hybrids possessing meta-nitro (26), para-fluoro (28), meta- and para-methyl (31), ortho-bromo (33) and ortho- and para-dimethyl (34) phenyl carboxamide scaffolds exhibited superior anti-inflammatory profiles over the standard diclofenac sodium. A hybrid integrated with a para-fluorophenyl carboxamide moiety (28) showed the highest DPPH radical scavenging activity among the chemical entities synthesized. Furthermore, the results of anticancer evaluations implied that the hybrid tethered with a phenyl carboxamide structural unit (29) exerted superior activity when compared with other hybrids against the pancreatic cancer cells SW1990 and AsPC1. Molecular docking between the hybrid 29 and B-cell lymphoma 2 reflects its appreciable binding affinity (-8.84 kcal mol-1). The results revealed that these chemical entities can serve as potent biological agents and/or efficient intermediates for the construction of potent biological agents.

5-Aminothiophene-2,4-dicarboxamide analogues as hepatitis B virus capsid assembly effectors

Chronic hepatitis B virus (HBV) infection represents a major health threat. Current FDA-approved drugs do not cure HBV. Targeting HBV core protein (Cp) provides an attractive approach toward HBV inhibition and possibly infection cure. We have previously identified and characterized a 5-amino-3-methylthiophene-2,4-dicarboxamide (ATDC) compound as a structurally novel hit for capsid assembly effectors (CAEs). We report herein hit validation through studies on absorption, distribution, metabolism and excretion (ADME) properties and pharmacokinetics (PK), and hit optimization via analogue synthesis aiming to probe the structure-activity relationship (SAR) and structure-property relationship (SPR). In the end, these medicinal chemistry efforts led to the identification of multiple analogues strongly binding to Cp, potently inhibiting HBV replication in nanomolar range without cytotoxicity, and exhibiting good oral bioavailability (F). Two of our analogues, 19o (EC50 = 0.11 μM, CC50 > 100 μM, F = 25%) and 19k (EC50 = 0.31 μM, CC50 > 100 μM, F = 46%), displayed overall lead profiles superior to reported CAEs 7–10 used in our studies.

Phenothiazine and amide-ornamented dihydropyridines: Via a molecular hybridization approach: Design, synthesis, biological evaluation and molecular docking studies

A series of novel phenothiazinyldihydropyridine dicarboxamides 7a-7j was synthesized by adopting a multi-step synthetic strategy and characterized through physical and spectral techniques. Among them, the chemical entities with para-fluoro (7d), ortho-bromo and-fluoro (7f and 7i), ortho- A nd para-methyl (7e) and meta- A nd para-methoxy (7h) substituents exhibited either similar or superior anti-inflammatory activities with respect to the standard drug diclofenac sodium. Besides, the chemical entities with ortho-bromo and-fluoro substituents as well as meta-nitro substituents (7f, 7g and 7i) showed enhanced radical scavenging activities when compared to standard ascorbic acid. Furthermore, anticancer studies revealed that the meta- A nd para-chloro-substituted molecule 7a exerted the best activity against all the pancreatic cancer cells tested. Also, appreciable binding affinity (-8.10 kcal mol-1) was observed during molecular docking between B-cell lymphoma 2 and 7a. The structural diversifications of the potent chemical entities besides further exploration in connection with the biological profiles of the same are underway.

Synthesis of β-Ketoamide Curcumin Analogs for Anti-Diabetic and AGEs Inhibitory Activities

Two different series of novel β-ketoamide curcumin analogs enriched in biological activities have been synthesized. The synthesized compounds were screened for their in?vitro anti-diabetic and AGEs inhibitory activities and exhibited potent to good anti-diabetic and AGEs inhibitory activities. The molecular docking study was also performed with the α-amylase enzyme.

Compounds having anticonvulsion activity, preparing methods thereof and applications of the compounds

The invention provides 7-substituted-5-methyl-1,2,4-triazolo[4,3-a] quinoline and 7-substituted-5-ethoxy-[1,2,4]-triazolo[4,3-a] quinoline compounds having anticonvulsion activity, preparing methods thereof and applications of the compounds in the field of preparing anticonvulsion medicines.