1226789-23-6

Basic information

• Product Name: ethyl 2-((4-chloro-3-fluorophenyl)amino)-2-oxoacetate
• Synonyms: ethyl 2-((4-chloro-3-fluorophenyl)amino)-2-oxoacetate
• CAS NO: 1226789-23-6
• Molecular Weight: 245.638
• Mol File: 1226789-23-6.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: ethyl 2-((4-chloro-3-fluorophenyl)amino)-2-oxoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-((4-chloro-3-fluorophenyl)amino)-2-oxoacetate(1226789-23-6)
• EPA Substance Registry System: ethyl 2-((4-chloro-3-fluorophenyl)amino)-2-oxoacetate(1226789-23-6)

Safety Data

• Hazardous Substances Data: 1226789-23-6(Hazardous Substances Data)

Upstream product

• 372-19-0 meta-fluoroaniline 
• 367-22-6 4-chloro-3-fluoroaniline 
• 4755-77-5 Ethyl oxalyl chloride 

Downstream Products

• 1098209-30-3 N¹-(4-chloro-3-fluorophenyl)-N²-(2,2,6,6-tetramethylpiperidin-4-yl) oxalamide 
• 1226787-87-6 N₁-(1-allyl-2,2,6,6-tetramethylpiperidin-4-yl)-N₂-(4-chloro-3-fluorophenyl)oxalamide 
• 1226787-88-7 N₁-(4-chloro-3-fluorophenyl)-N₂-(2,2,6,6-tetramethyl-1-(prop-2-ynyl)piperidin-4-yl)oxalamide 
• 1430823-67-8 C₂₃H₃₁ClFN₃O₂ 
• 1443787-34-5 N¹-(4-chloro-3-fluorophenyl)-N²-(2-(methylamino)-2-oxo-1-phenylethyl)oxalamide 
• 1422851-50-0 N¹-(4-chloro-3-fluorophenyl)-N²-((1R,2S)-2-(hydroxymethyl)-2,3-dihydro-1H-inden-1-yl)oxalamide 
• 1422851-70-4 [(1R,2S)-1-{(2-((4-chloro-3-fluorophenyl)amino)-2-oxoacetamido)-2,3-dihydro-1H-inden-2-yl}methyl] methanesulfonate 
• 1422851-73-7 N¹-((1R,2R)-2-(azidomethyl)-2,3-dihydro-1H-inden-1-yl)-N²-(4-chloro-3-fluorophenyl) oxalamide 
• 1422851-67-9 N¹-((1R,2R)-2-(aminomethyl)-2,3-dihydro-1H-inden-1-yl)-N²-(4-chloro-3-fluorophenyl)-oxalamide 
• 1422851-31-7 (+)-N¹-(4-chloro-3-fluorophenyl)-N²-(trans-2-(guanidinomethyl)indan-1-yl)oxalamide formate salt 

Relevant articles and documents

Phenyl-oxamideHIV-1 inhibitors and preparation method and application thereof

The invention relates to phenyl-oxamideHIV-1 inhibitors and a preparation method and application thereof. Compounds have the structure shown in the formula I. The invention further relates to drug compositions containing the compounds with the structure s

CD4 mimics as HIV entry inhibitors: Lead optimization studies of the aromatic substituents

Several CD4 mimics have been reported as HIV-1 entry inhibitors that can intervene in the interaction between a viral envelope glycoprotein gp120 and a cell surface protein CD4. Our previous SAR studies led to a finding of a highly potent analogue 3 with bulky hydrophobic groups on a piperidine moiety. In the present study, the aromatic ring of 3 was modified systematically in an attempt to improve its antiviral activity and CD4 mimicry which induces the conformational changes in gp120 that can render the envelope more sensitive to neutralizing antibodies. Biological assays of the synthetic compounds revealed that the introduction of a fluorine group as a meta-substituent of the aromatic ring caused an increase of anti-HIV activity and an enhancement of a CD4 mimicry, and led to a novel compound 13a that showed twice as potent anti-HIV activity compared to 3 and a substantial increase in a CD4 mimicry even at lower concentrations.

Design, synthesis, and antiviral activity of entry inhibitors that target the CD4-binding site of HIV-1

The CD4 binding site on HIV-1 gp120 has been validated as a drug target to prevent HIV-1 entry to cells. Previously, we identified two small molecule inhibitors consisting of a 2,2,6,6-tetramethylpiperidine ring linked by an oxalamide to a p-halide-substituted phenyl group, which target this site, specifically, a cavity termed "Phe43 cavity". Here we use synthetic chemistry, functional assessment, and structure-based analysis to explore variants of each region of these inhibitors for improved antiviral properties. Alterations of the phenyl group and of the oxalamide linker indicated that these regions were close to optimal in the original lead compounds. Design of a series of compounds, where the tetramethylpiperidine ring was replaced with new scaffolds, led to improved antiviral activity. These new scaffolds provide insight into the surface chemistry at the entrance of the cavity and offer additional opportunities by which to optimize further these potential-next- generation therapeutics and microbicides against HIV-1.