157033-24-4

Usage

Uses

Used in Pharmaceutical Synthesis:
2-(3,5-DIFLUOROPHENYL)ETHANOYL CHLORIDE is used as a key intermediate for the synthesis of various pharmaceuticals. It serves as a reagent for the introduction of the 3,5-difluorophenylacetyl group into different compounds, contributing to the development of new drugs with specific therapeutic properties.
Used in Agrochemical Production:
In the agrochemical industry, 2-(3,5-DIFLUOROPHENYL)ETHANOYL CHLORIDE is utilized as a building block for the production of various agrochemicals. Its reactivity allows for the creation of compounds with pesticidal or herbicidal properties, enhancing crop protection and yield.
Used in Organic Synthesis:
2-(3,5-DIFLUOROPHENYL)ETHANOYL CHLORIDE is employed as a reagent in organic synthesis for the introduction of the 3,5-difluorophenylacetyl group into a wide range of organic compounds. This modification can alter the chemical and physical properties of these compounds, expanding their potential applications in various fields.
Safety Considerations:
Due to its high reactivity and potential irritant properties, 2-(3,5-DIFLUOROPHENYL)ETHANOYL CHLORIDE should be handled with care in a controlled laboratory environment to minimize risks to skin, eyes, and the respiratory system. Proper safety measures, including the use of personal protective equipment, should be strictly followed during its use and storage.

InChI:InChI=1/C8H5ClF2O/c9-8(12)3-5-1-6(10)4-7(11)2-5/h1-2,4H,3H2

Upstream product

• 79-37-8 oxalyl dichloride 
• 105184-38-1 3,5-difluorophenyl acetic acid 
• 210530-70-4 methyl 2-(3,5-difluorophenyl)acetate 

Downstream Products

• 228718-03-4 dimethyl-2-(2'-(3',5'-difluorophenyl)acetyl)-2-(2'-(4'-(methylsulfonyl)phenyl)-2'-oxoethyl)propane-1,3-dioate 
• 172366-38-0 5,7-difluoro-3,4-dihydro-2(1H)-naphthalenone 
• 208124-34-9 N-(3,5-Difluorophenylacetyl)-L-alanine 
• 1086682-85-0 2-(3,5-difluorophenyl)-N-(4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)acetamide 
• 1332344-63-4 2-(3,5-difluorophenyl)-2,2-difluoro-N-phenylacetamide 
• 1246040-71-0 N-{6-[(6-chloro-pyridin-3-ylmethyl)-amino]-2-pyrrolidin-1-yl-pyridin-3-yl}-2-(3,5-difluoro-phenyl)-acetamide 
• 1242158-45-7 2-(3,5-difluoro-phenyl)-N-{4-methyl-6-morpholin-4-yl-2-[(tetrahydro-pyran-4-ylmethyl)-amino]-pyrimidin-5-yl}-acetamide 
• 1228076-12-7 2-(3,5-difluorophenyl)-N-[6-(4-fluorobenzylamino)-2-(morpholin-4-yl)pyridin-3-yl]acetamide 
• 1093123-02-4 C₁₄H₄Cl₄F₂O₃ 
• 1080450-95-8 2-(3,5-difluoro-phenyl)-N-[3-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-4'-trifluoromethyl-biphenyl-4-yl]-acetamide 
• 1080450-80-1 N-[4-bromo-2-(1H-tetrazol-5-yl)-phenyl]-2-(3,5-difluoro-phenyl)-acetamide 
• 473736-97-9 4-{[2-(3,5-difluoro-phenyl)-acetylamino]-methyl}-4-(4-iodo-phenyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 228718-04-5 methyl-3-(3',5'-difluorophenyl)-1-(methoxycarbonyl)-4-(4'-(methylsulfonyl)phenyl)-2-oxocyclopent-3-enecarboxylate 
• 212126-32-4 2-(3,5-difluorophenyl)-3-(4-(methylsulfonyl)phenyl)-2-cyclopenten-1-one 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of novel pyrrolidone-based derivatives as potent p53-MDM2 inhibitors

Inhibition of the interactions of the tumor suppressor protein p53 with its negative regulators MDM2 in vitro and in vivo, representing a valuable therapeutic strategy for cancer treatment. The natural product chalcone exhibited moderate inhibitory activity against MDM2, thus based on the binding mode between chalcone and MDM2, a hit unsaturated pyrrolidone scaffold was obtained through virtual screening. Several unsaturated pyrrolidone derivatives were synthesized and biological evaluated. As a result, because the three critical hydrophobic pockets of MDM2 were occupied by the substituted-phenyl linked at the pyrrolidone fragment, compound 4 h demonstrated good binding affinity with the MDM2. Additionally, compound 4 h also showed excellent antitumor activity and selectivity, and no cytotoxicity against normal cells in vitro. The further antitumor mechanism studies were indicated that compound 4 h could successfully induce the activation of p53 and corresponding downstream p21 proteins, thus successfully causing HCT116 cell cycle arrest in the G1/M phase and apoptosis. Thus, the novel unsaturated pyrrolidone p53-MDM2 inhibitors could be developed as novel antitumor agents.

Important intermediate of nepicastat, and enzymatic synthesis method thereof

The invention discloses an important intermediate of nepicastat, and an enzymatic synthesis method thereof. The important intermediate concretely is (R)-5,7-difluoro-1,2,3,4-tetrahydronaphthalene-2-ol. The raw material of the synthesis method is 3,5-diflu

Phosphonic acid analogs of fluorophenylalanines as inhibitors of human and porcine aminopeptidases N: Validation of the importance of the substitution of the aromatic ring

A library of phosphonic acid analogs of phenylalanine substituted with fluorine, chlorine and trifluoromethyl moieties on the aromatic ring was synthesized and evaluated for inhibitory activity against human (hAPN) and porcine (pAPN) aminopeptidases. Fluorogenic screening indicated that these analogs are micromolar or submicromolar inhibitors, both enzymes being more active against hAPN. In order to better understand the mode of the action of the most active compounds, molecular modeling was used. It confirmed that aminophosphonic portion of the enzyme is bound nearly identically in the case of all the studied compounds, whereas the difference in activity results from the placement of aromatic side chain of an inhibitor. Interestingly, both enantiomers of the individual compounds are usually bound quite similarly.

Formation of Non-Natural α,α-Disubstituted Amino Esters via Catalytic Michael Addition

The enolate monoanion of amino esters is explored, and the first catalytic Michael addition of α-amino esters is demonstrated. These studies indicate that the acidity of the αC-H is the primary factor determining reactivity. Thus, polyfluorophenylglycine amino esters yield novel α-amino esters in the presence of a catalytic amount of a guanidine-derived base and Michael acceptors. Reactivity requires an acidic N-H, which is accomplished using common protecting groups such as N-Bz, N-Boc, and N-Cbz. Calculations and labeling experiments provide insight into the governing principles in which a key C-to-N proton transfer occurs, resulting in an expansion of the scope to include a number of natural amino esters. The study culminates with a late-stage functionalization of peptidic γ-secretase inhibitor, DAPT.

Diphenylurea derivatives for combating methicillin- and vancomycin-resistant Staphylococcus aureus

A new class of diphenylurea was identified as a novel antibacterial scaffold with an antibacterial spectrum that includes highly resistant staphylococcal isolates, namely methicillin- and vancomycin-resistant Staphylococcus aureus (MRSA & VRSA). Starting with a lead compound 3 that carries an aminoguanidine functionality from one side and a n-butyl moiety on the other ring, several analogues were prepared. Considering the pharmacokinetic parameters as a key factor in structural optimization, the structure-activity-relationships (SARs) at the lipophilic side chain were rigorously examined leading to the discovery of the cycloheptyloxyl analogue 21n as a potential drug-candidate. This compound has several notable advantages over vancomycin and linezolid including rapid killing kinetics against MRSA and the ability to target and reduce the burden of MRSA harboring inside immune cells (macrophages). Furthermore, the potent anti-MRSA activity of 21n was confirmed in?vivo using a Caenorhabditis elegans animal model. The present study provides a foundation for further development of diphenylurea compounds as potential therapeutic agents to address the burgeoning challenge of bacterial resistance to antibiotics.

METHODS FOR TREATING DEPENDENCE

no abstract published

DERIVATIVES OF 2,3-DIPHENYLCHROMENE USEFUL FOR THE TREATMENT OF CANCER

Described herein are compounds that are estrogen receptor modulators of Formula I and stereoisomers, tautomers, or pharmaceutically acceptable salts thereof, and with the substituents and structural features described herein. Also described are pharmaceutical compositions and medicaments that include the compounds described herein, as well as methods of using such estrogen receptor modulators, alone and in combination with other compounds, for treating diseases or conditions that are mediated or dependent upon estrogen receptors.

The human Aurora kinase inhibitor danusertib is a lead compound for anti-trypanosomal drug discovery via target repurposing

New drugs for neglected tropical diseases such as human African trypanosomiasis (HAT) are needed, yet drug discovery efforts are not often focused on this area due to cost. Target repurposing, achieved by the matching of essential parasite enzymes to those human enzymes that have been successfully inhibited by small molecule drugs, provides an attractive means by which new drug optimization programs can be pragmatically initiated. In this report we describe our results in repurposing an established class of human Aurora kinase inhibitors, typified by danusertib (1), which we have observed to be an inhibitor of trypanosomal Aurora kinase 1 (TbAUK1) and effective in parasite killing in vitro. Informed by homology modeling and docking, a series of analogs of 1 were prepared that explored the scope of the chemotype and provided a nearly 25-fold improvement in cellular selectivity for parasite cells over human cells.

Optimizing small molecule inhibitors of calcium-dependent protein kinase 1 to prevent infection by toxoplasma gondii

Toxoplasma gondii is sensitive to bulky pyrazolo [3,4-d] pyrimidine (PP) inhibitors due to the presence of a Gly gatekeeper in the essential calcium dependent protein kinase 1 (CDPK1). Here we synthesized a number of new derivatives of 3-methyl-benzyl-PP (3-MB-PP, or 1). The potency of PP analogues in inhibiting CDPK1 enzyme activity in vitro (low nM IC50 values) and blocking parasite growth in host cell monolayers in vivo (low μM EC 50 values) were highly correlated and occurred in a CDPK1-specific manner. Chemical modification of the PP scaffold to increase half-life in the presence of microsomes in vitro led to identification of compounds with enhanced stability while retaining activity. Several of these more potent compounds were able to prevent lethal infection with T. gondii in the mouse model. Collectively, the strategies outlined here provide a route for development of more effective compounds for treatment of toxoplasmosis and perhaps related parasitic diseases.

SUBSTITUTED PYRIDINE DERIVATIVES AND THEIR MEDICAL USE

The present application discloses novel substituted 1,4-oxazepanyl-pyridine derivatives and their use as modulators of the voltage gated KV7 (KCNQ) potassium ion channels. In other aspects the application discloses the use of these compounds, i