88023-07-8

Usage

Uses

Used in Pharmaceutical Industry:
2-(4-Fluorobenzyl)acetoacetic acid ethyl ester is used as a building block for the preparation of various pharmaceuticals. Its unique structure allows for the creation of new drugs and biologically active molecules, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical industry, 2-(4-Fluorobenzyl)acetoacetic acid ethyl ester serves as a key component in the synthesis of agrochemicals. Its properties make it suitable for the development of new pesticides, herbicides, and other agricultural chemicals to improve crop protection and yield.
Used in Organic Synthesis:
2-(4-Fluorobenzyl)acetoacetic acid ethyl ester is used as a reagent in organic synthesis for the preparation of diverse heterocycles and other organic compounds. Its versatility and the presence of the fluorobenzyl group make it a valuable intermediate in the synthesis of complex organic molecules.
Used in Drug Discovery:
2-(4-FLUOROBENZYL)ACETOACETIC ACID ETHYL ESTER is utilized in drug discovery processes due to its potential to contribute to the development of new drugs. Its unique structure and the presence of the fluorobenzyl group make it a promising candidate for the creation of innovative pharmaceutical agents with improved efficacy and selectivity.

Upstream product

• 352-11-4 1-chloromethyl-4-fluorobenzene 
• 141-97-9 ethyl acetoacetate 
• 459-46-1 4-Fluorobenzyl bromide 

Downstream Products

• 63416-61-5 4-(4-fluorophenyl)-2-butanone 
• 548764-04-1 3-(4-fluorobenzyl)-7-hydroxy-4-methyl-2H-chromen-2-one 
• 63416-82-0 3-(4-fluorophenyl)-1,1-dimethylpropanol 
• 63416-84-2 3-(4-fluorophenyl)-1,1-dimethylpropanamine 
• 143627-96-7 N-[3-(4-Fluoro-phenyl)-1,1-dimethyl-propyl]-formamide 
• 143627-93-4 N-<3-(4-fluorophenyl)-1,1-dimethylpropyl>thiourea 
• 143627-92-3 1-Benzoyl-3-[3-(4-fluoro-phenyl)-1,1-dimethyl-propyl]-thiourea 
• 143627-75-2 N-Benzoyl-N'-[3-(4-fluoro-phenyl)-1-methyl-propyl]-N''-[3-(1H-imidazol-4-yl)-propyl]-guanidine 
• 63659-85-8 3-(4-fluorophenyl)-1-methylpropylamine 
• 932707-48-7 [8-chloro-3-(4-fluorobenzyl)-2-methyl-4-oxo-1,4-dihydroquinolin-5-yloxy]acetic acid methyl ester 
• 932707-49-8 [8-chloro-3-(4-fluorobenzyl)-4-methyl-2-oxo-1,2-dihydroquinolin-5-yloxy]acetic acid methyl ester 
• 1091602-28-6 C₁₇H₁₈FN₃O₄S 
• 1335026-80-6 2-amino-6-[(4-fluorophenyl)methyl]-5-methyl-4H-[1,2,4]triazolo[5,1-b]pyrimidin-7-one 
• 577775-54-3 2-(4-fluorobenzyl)-3-methyl-1-oxo-1H,5H-pyrido[1,2-a]benzimidazole-4-carbonitrile 

Relevant academic research and scientific papers

Mechanistic Investigations of Metallo-β-lactamase Inhibitors: Strong Zinc Binding Is Not Required for Potent Enzyme Inhibition**

Metallo-β-lactamases (MBLs) are zinc-dependent bacterial enzymes that inactivate essentially all classes of β-lactam antibiotics including last-resort carbapenems. At present there are no clinically approved MBL inhibitors, and in order to develop such ag

Development of coumarine derivatives as potent anti-filovirus entry inhibitors targeting viral glycoprotein

Filoviruses, including Ebolavirus (EBOV), Marburgvirus (MARV) and Cuevavirus, cause hemorrhagic fevers in humans with up to 90% mortality rates. In the 2014–2016 West Africa Ebola epidemic, there are 15,261 laboratory confirmed cases and 11,325 total deaths. The lack of effective vaccines and medicines for the prevention and treatment of filovirus infection in humans stresses the urgency to develop antiviral therapeutics against filovirus-associated diseases. Our previous study identified a histamine receptor antagonist compound CP19 as an entry inhibitor against both EBOV and MARV. The preliminary structure-activity relationship (SAR) studies of CP19 showed that its piperidine, coumarin and linker were related with its antiviral activities. In this study, we performed detailed SAR studies on these groups with synthesized CP19 derivatives. We discovered that 1) the piperidine group could be optimized with heterocycles, 2) the substitution groups of C3 and C4 of coumarin should be relatively large hydrophobic groups and 3) the linker part should be least substituted. Based on the SAR analysis, we synthesized compound 32 as a potent entry inhibitor of EBOV and MARV (IC50 = 0.5 μM for EBOV and 1.5 μM for MARV). The mutation studies of Ebola glycoprotein and molecular docking studies showed that the coumarin and its substituted groups of compound 32 bind to the pocket of Ebola glycoprotein in a similar way to the published entry inhibitor compound 118a. However, the carboxamide group of compound 32 does not have strong interaction with N61 as compound 118a does. The coumarin skeleton structure and the binding model of compound 32 elucidated by this study could be utilized to guide further design and optimization of entry inhibitors targeting the filovirus glycoproteins.

α-Arylation of Carbonyl Compounds through Oxidative C?C Bond Activation

A synthetically useful approach for the direct α-arylation of carbonyl compounds through a novel oxidative C?C bond activation is reported. This mechanistically unusual process relies on a 1,2-aryl shift and results in all-carbon quaternary centers. The transformation displays broad functional-group tolerance and can in principle also be applied as an asymmetric variant.

3-substituted coumarin furazan derivatives and application of derivatives in preparation of anti-multidrug resistance tumor drugs

The invention belongs to the field of chemical pharmacy, and relates to furazan conjugates obtained by a combination of a 3-substituted coumarin mother nucleus, a derivative substituted by alpha,beta-unsaturated ketone, and furoxan through two-carbon link

Tunable Aerobic Oxidative Hydroxylation/Dehydrogenative Homocoupling of Pyrazol-5-ones under Transition-Metal-Free Conditions

A practical and tunable transition-metal-free aerobic oxidation of pyrazol-5-ones preparing either 4-hydroxypyrazoles (via C-H hydroxylation) or bispyrazoles (via dehydrogenative homocoupling) is described. The K2CO3/dioxane reagent system predominately promoted hydroxylation to deliver the α-hydroxylated pyrazoles. In contrast, the formation of bispyrazoles was overwhelmingly preferred with CH3CN as the reaction medium without any additives.

Substituted 3-benzylcoumarins as allosteric MEK1 inhibitors: Design, synthesis and biological evaluation as antiviral agents

In order to find novel antiviral agents, a series of allosteric MEK1 inhibitors were designed and synthesized. Based on docking results, multiple optimizations were made on the coumarin scaffold. Some of the derivatives showed excellent MEK1 binding affinity in the appropriate enzymatic assays and displayed obvious inhibitory effects on the ERK pathway in a cellular assay. These compounds also significantly inhibited virus (EV71) replication in HEK293 and RD cells. Several compounds showed potential as agents for the treatment of viral infective diseases, with the most potent compound 18 showing an IC 50 value of 54.57 nM in the MEK1 binding assay.

Pyrido[1,2-a]benzimidazole-Based Agents Active Against Tuberculosis (TB), Multidrug-Resistant (MDR) TB and Extensively Drug-Resistant (XDR) TB

The struggle against tuberculosis (TB) is still far from over. TB, caused by Mycobacterium tuberculosis, is one of the deadliest infections worldwide. Co-infection with human immunodeficiency virus (HIV) and the emergence of multidrug-resistant tuberculos

Carbonic anhydrase inhibitors: Synthesis and inhibition studies against mammalian isoforms I-XV with a series of 2-(hydrazinocarbonyl)-3-substituted-phenyl-1H-indole-5-sulfonamides

A series of 2-(hydrazinocarbonyl)-3-substitutedphenyl-1H-indole-5-sulfonamides possessing various 2-, 3- or 4- substituted phenyl groups with methyl-, halogeno- and methoxy- functionalities, as well as the perfluorophenyl moiety have been synthesized and

QUINOLINES AND THEIR THERAPEUTIC USE

Compounds of formula [1] are CRTH2 antagonists, useful in the treatment of conditions having an inflammatory component; in which: R1, R2, R3, R4 and R5 are independently hydrogen, C1-C6alkyl, C1- C6fluoroalkyl, cyclopropyl, halo, -S(O)nR6, -SO2NR7R8, -NR7R8, -NR7C(O)R6, -CO2R7, -C(O)NR7R8, -C(O)R6, -NO2, -CN or a group -OR9; wherein each R6 is independently C1-C6alkyl, C1-C6fluoroalkyl, cycloalkyl, aryl, or heteroaryl; R7, R8 are independently C1-C6alkyl, C1-C6fluoroalkyl, cycloalkyl, cycloalkyl-(C1-C6alkyl)-, aryl, heteroaryl or hydrogen; R9 is hydrogen, C1-C6alkyl, C1-C6fluoroalkyl, cycloalkyl, cylcoalkyl-(C1-C6alkyl)-, or a group -SO2R6; A is -CHR10-, -C(O)-, -S(O)n-, -0-, or -NR10- wherein n is an integer from 0-2 and R10 is hydrogen, C1-C3alkyl, or C1-C6fluoroalkyl group; B is a direct bond, or a divalent radical selected from -CH2-, -CH2CH2-, -CHR11-, -CR11R12-, -CH2CHR11-, -CH2CR11R12-, -CHR11CHR12-, and divalent radicals of formula -(CR11R12)P-Z- wherein Z is attached to the ring carrying R1, R2 and R3; wherein R11 is C1-C3alkyl, cyclopropyl, C1-C6fluoroalkyl; R12 is methyl or fluoromethyl; p is independently 1 or 2; and Z is -0-, -NH-, or -S(O)n-, wherein n is an integer from 0-2; X is a carboxylic acid, tetrazole, 3-hydroxyisoxazole, hydroxamic acid, phosphinate, phosphonate, phosphonamide, or sulfonic acid group, or a group of formula C(=O)NHSO2R6or SO2NHC(=O)R6; and Y is aryl, heteroaryl, aryl-fused- heterocycloalkyl, heteroaryl-fused-cycloalkyl, heteroaryl-fused-heterocycloalkyl or aryl-fused-cycloalkyl group.

2-OXO-2H-CHROMENE COMPOUNDS

Compounds of structural formula (1) modulate CRTH2 activity and are of utility in, for example, respiratory diseases formula (1): in which: A represents a direct bond, an optionally substituted alkylene or alkenylene group, or a group of formula Z-(optionally substituted)alkylene; B represents a direct bond, an optionally substituted alkylene or alkenylene group, or a group of formula Z-(optionally substituted)alkylene or (optionally substituted)alkylene-Z; Z represents an oxygen atom, an NH or N-alkyl group, or a group of formula S(O)n, in which n = 0 to 2; X represents a carboxylic acid, tetrazole, 3-hydroxyisoxazole, hydroxamic acid, phosphinate, phosphonate, phosphonamide, sulfonic acid or a group of formula C(=O)NHSO2W or SO2NHC(=O)W; W represents an optionally substituted aryl or heteroaryl group or an optionally substituted alkyl or cycloalkyl group; Y represents an optionally substituted phenyl or 5- or 6-membered heteroaryl group, Ra, Rb, and Rc independently represent hydrogen, acyl, alkoxy, alkoxycarbonyl, alkylamino, alkylsulfinyl, alkylsulfonyl, alkylthio, -NH2, aminoalkyl, hydroxyalkyl, alkoxyalkyl, arylalkyl, cyano, dialkylamino, halo, haloalkoxy, haloalkyl, alkyl, alkenyl, -OH, optionally substituted aryl, optionally substituted heteroaryl, heterocycloalkyl, aminoacyl, aminosulfonyl, acylamino, sulfonylamino, heteroarylalkyl, cyclic amino, aryloxy, heteroaryloxy, arylalkyloxy or heteroarylalkyloxy.