N-hydroxy-2-(N-isopropoxybiphenyl-4-ylsulfonamido)acetamide

Base Information

• Chemical Name: N-hydroxy-2-(N-isopropoxybiphenyl-4-ylsulfonamido)acetamide
• CAS No.: 704888-90-4
• Molecular Formula: C₁₇H₂₀N₂O₅S
• Molecular Weight: 364.422
• Hs Code.: 2935009090
• DSSTox Substance ID: DTXSID30434718
• Wikidata: Q27074512
• Pharos Ligand ID: ZKCTB42VUC15
• ChEMBL ID: CHEMBL181244
• Mol file: 704888-90-4.mol

Synonyms:ARP-100;N-hydroxy-2-((4-phenylphenyl)sulfonylpropan-2-yloxyamino)acetamide

Chemical Property of N-hydroxy-2-(N-isopropoxybiphenyl-4-ylsulfonamido)acetamide

Chemical Property:

• PSA: 104.32000
• LogP: 3.66140
• Storage Temp.: Desiccate at +4°C
• Solubility.: Soluble at 100mM in DMSO
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 364.10929292
• Heavy Atom Count: 25
• Complexity: 518

Purity/Quality:

99%min ^*data from raw suppliers

ARP 100 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)ON(CC(=O)NO)S(=O)(=O)C1=CC=C(C=C1)C2=CC=CC=C2
• Uses: ARP 100 is a potent, dual inhibitor of MMP-12/MMP-13 targets, which are a family of zinc dependent endopeptidases known to play key roles in extracellular matrix (ECM) breakdown disorders, such as the two main forms of arthritis, rheumatoid arthritis (RA) and osteoarthritis (OA). A selective inhibitor of MMP-2

Technology Process of N-hydroxy-2-(N-isopropoxybiphenyl-4-ylsulfonamido)acetamide

There total 5 articles about N-hydroxy-2-(N-isopropoxybiphenyl-4-ylsulfonamido)acetamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

[(isopropoxy)(1,1'-biphenyl-4-ylsulfonyl)amino]acetic acid O-(tert-butyldimethylsilyl)hydroxyamide (704889-13-4) → ARP 100 (704888-90-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 5h;

DOI:10.1016/j.bmc.2004.01.047

Reference yield:

4-diphenylsulfonyl chloride (1623-93-4) → ARP 100 (704888-90-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 83 percent / N-methylmorpholine / tetrahydrofuran / 96 h / 20 °C

2: 34 percent / caesium carbonate; tetrabutylammonium hydrogensulfate / dimethylformamide / 72 h / 20 °C

3: trifluoroacetic acid / CH₂Cl₂ / 5 h / 0 °C

4: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 20 h / 20 °C

5: trifluoroacetic acid / CH₂Cl₂ / 5 h / 0 °C

With 4-methyl-morpholine; tetra(n-butyl)ammonium hydrogensulfate; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2004.01.047

Reference yield:

N-isopropoxy-1,1'-biphenyl-4-sulfonamide (704888-95-9) → ARP 100 (704888-90-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 34 percent / caesium carbonate; tetrabutylammonium hydrogensulfate / dimethylformamide / 72 h / 20 °C

2: trifluoroacetic acid / CH₂Cl₂ / 5 h / 0 °C

3: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 20 h / 20 °C

4: trifluoroacetic acid / CH₂Cl₂ / 5 h / 0 °C

With tetra(n-butyl)ammonium hydrogensulfate; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2004.01.047

upstream raw materials:

[(isopropoxy)(1,1'-biphenyl-4-ylsulfonyl)amino]acetic acid O-(tert-butyldimethylsilyl)hydroxyamide

4-diphenylsulfonyl chloride

N-isopropoxy-1,1'-biphenyl-4-sulfonamide

[(isopropoxy)(1,1'-biphenyl-4-ylsulfonyl)amino]acetic acid

Refernces