1422851-50-0

Basic information

• Product Name: N¹-(4-chloro-3-fluorophenyl)-N²-((1R,2S)-2-(hydroxymethyl)-2,3-dihydro-1H-inden-1-yl)oxalamide
• Synonyms: N¹-(4-chloro-3-fluorophenyl)-N²-((1R,2S)-2-(hydroxymethyl)-2,3-dihydro-1H-inden-1-yl)oxalamide
• CAS NO: 1422851-50-0
• Molecular Weight: 362.788
• Mol File: 1422851-50-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N¹-(4-chloro-3-fluorophenyl)-N²-((1R,2S)-2-(hydroxymethyl)-2,3-dihydro-1H-inden-1-yl)oxalamide(CAS DataBase Reference)
• NIST Chemistry Reference: N¹-(4-chloro-3-fluorophenyl)-N²-((1R,2S)-2-(hydroxymethyl)-2,3-dihydro-1H-inden-1-yl)oxalamide(1422851-50-0)
• EPA Substance Registry System: N¹-(4-chloro-3-fluorophenyl)-N²-((1R,2S)-2-(hydroxymethyl)-2,3-dihydro-1H-inden-1-yl)oxalamide(1422851-50-0)

Safety Data

• Hazardous Substances Data: 1422851-50-0(Hazardous Substances Data)

Upstream product

• 18096-63-4 cis-1-Hydroxy-2-hydroxymethylindan 
• 6742-25-2 1-oxoindane-2-carboxylic acid ethyl ester 
• 83-33-0 inden-1-one 
• 1422851-66-8 N¹-(4-chloro-3-fluorophenyl)-N²-((1R,2R)-2-(hydroxymethyl)-2,3-dihydro-1H-inden-1-yl)oxalamide 
• 55269-97-1 [(1R,2R)-1-amino-2,3-dihydro-1H-inden-2-yl] methanol 
• 135053-20-2 (1R,2R)-1-amino-2,3-dihydro-1H-indene-2-carboxylic acid 
• 1226789-23-6 ethyl 2-((4-chloro-3-fluorophenyl)amino)-2-oxoacetate 
• 95-13-6 1-indene 

Downstream Products

• 1422851-70-4 [(1R,2S)-1-{(2-((4-chloro-3-fluorophenyl)amino)-2-oxoacetamido)-2,3-dihydro-1H-inden-2-yl}methyl] methanesulfonate 
• 1422851-39-5 (-)-N¹-(4-chloro-3-fluorophenyl)-N²-(trans-2-(guanidinomethyl)indan-1-yl)oxalamide formate salt 
• 1422851-31-7 (+)-N¹-(4-chloro-3-fluorophenyl)-N²-(trans-2-(guanidinomethyl)indan-1-yl)oxalamide formate salt 
• 1422851-67-9 N¹-((1R,2R)-2-(aminomethyl)-2,3-dihydro-1H-inden-1-yl)-N²-(4-chloro-3-fluorophenyl)-oxalamide 
• 1422851-73-7 N¹-((1R,2R)-2-(azidomethyl)-2,3-dihydro-1H-inden-1-yl)-N²-(4-chloro-3-fluorophenyl) oxalamide 

Relevant articles and documents

INHIBITORS OF HIV-1 ENTRY AND METHODS OF USE THEREOF

The disclosure provides compositions and methods for sensitizing primary HIV-1, including transmitted/founder viruses, to neutralization by monoclonal antibodies, e.g., those directed against CD4-induced (CD4i) epitopes and the V3 region. In certain embodiments, the disclosure relates to the use of small molecules as microbicides to inhibit HIV-1 infection directly and to sensitize primary HIV-1 to neutralization by readily elicited antibodies.

Structure-based design and synthesis of an HIV-1 entry inhibitor exploiting X-ray and thermodynamic characterization

The design, synthesis, thermodynamic and crystallographic characterization of a potent, broad spectrum, second-generation HIV-1 entry inhibitor that engages conserved carbonyl hydrogen bonds within gp120 has been achieved. The optimized antagonist exhibits a submicromolar binding affinity (110 nM) and inhibits viral entry of clade B and C viruses (IC50 geometric mean titer of 1.7 and 14.0 μM, respectively), without promoting CD4-independent viral entry. The thermodynamic signatures indicate a binding preference for the (R,R)- over the (S,S)-enantiomer. The crystal structure of the small-molecule/gp120 complex reveals the displacement of crystallographic water and the formation of a hydrogen bond with a backbone carbonyl of the bridging sheet. Thus, structure-based design and synthesis targeting the highly conserved and structurally characterized CD4-gp120 interface is an effective tactic to enhance the neutralization potency of small-molecule HIV-1 entry inhibitors.