N-(2-(4'-Cyano-[1,1'-biphenyl]-4-yl)propyl)propane-2-sulfonamide

Base Information

• Chemical Name: N-(2-(4'-Cyano-[1,1'-biphenyl]-4-yl)propyl)propane-2-sulfonamide
• CAS No.: 211311-95-4
• Molecular Formula: C₁₉H₂₂N₂O₂S
• Molecular Weight: 342.462
• Hs Code.: 2935009090
• UNII: 75W6I8W6OU
• DSSTox Substance ID: DTXSID00432983
• Nikkaji Number: J1.444.877B
• Wikipedia: LY-404187
• Wikidata: Q6460433
• Pharos Ligand ID: 2CG6RZDNCYL4
• ChEMBL ID: CHEMBL435582
• Mol file: 211311-95-4.mol

Synonyms:LA451646;LY 404187;LY-404187;LY404187;LY451646

Chemical Property of N-(2-(4'-Cyano-[1,1'-biphenyl]-4-yl)propyl)propane-2-sulfonamide

Chemical Property:

• PSA: 78.34000
• LogP: 5.12828
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 342.14019912
• Heavy Atom Count: 24
• Complexity: 527

Purity/Quality:

98% min ^*data from raw suppliers

LY 404187 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)S(=O)(=O)NCC(C)C1=CC=C(C=C1)C2=CC=C(C=C2)C#N
• Description: LY404187 is a benzothiadiazide positive allosteric modulator of AMPA receptors. It increases glutamate-induced activation of GluR1i, -2i, -2o, -3i, and -4i subunit-containing AMPA receptors with EC50 values of 5.65, 0.15, 1.44, 1.66, and 0.21 μM, respectively, in a calcium influx assay. LY404187 is selective for these AMPA receptors over GluR6 subunit-containing kainate receptors at 10 μM. LY404187 increases currents induced by glutamate and AMPA in rat prefrontal cortex pyramidal neurons (EC50s = 1.3 and 1.2 μM, respectively) but not in AMPA-stimulated primary rat embryonic hippocampal or primary cerebellar Purkinje neurons. LY404187 prevents decreases in the number of dopaminergic neurons in the substantia nigra induced by MPTP and 6-OHDA in mouse and rat, respectively, models of Parkinson’s disease when administered at a dose of 0.5 mg/kg per day.
• Uses: LY 404187 is a novel positive allosteric modulator of AMPA receptors.

Technology Process of N-(2-(4'-Cyano-[1,1'-biphenyl]-4-yl)propyl)propane-2-sulfonamide

There total 60 articles about N-(2-(4'-Cyano-[1,1'-biphenyl]-4-yl)propyl)propane-2-sulfonamide 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:

4-cyanophenylboronic acid (126747-14-6) + propane-2-sulfonic acid (2-(4-bromo-phenyl)-propyl)-amide (211311-65-8) → LY 404187 (211311-95-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In 1,4-dioxane; water; at 100 ℃;

DOI:10.1021/jm0002836

Reference yield:

4-Bromophenylacetonitrile (16532-79-9) → LY 404187 (211311-95-4)

Guidance literature:

Multi-step reaction with 4 steps

1: K₂CO₃ / 16 h / 180 °C

2: BH₃*SMe₂ / tetrahydrofuran / Heating

3: Et₃N / CH₂Cl₂ / 0 - 20 °C

4: K₂CO₃; Pd(PPh₃)4 / dioxane; H₂O / 100 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; dimethylsulfide borane complex; potassium carbonate; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; 4: Suzuki coupling;

DOI:10.1021/jm0002836

Reference yield:

2-(4-Bromophenyl)propionitrile (42186-06-1) → LY 404187 (211311-95-4)

Guidance literature:

Multi-step reaction with 3 steps

1: BH₃*SMe₂ / tetrahydrofuran / Heating

2: Et₃N / CH₂Cl₂ / 0 - 20 °C

3: K₂CO₃; Pd(PPh₃)4 / dioxane; H₂O / 100 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; dimethylsulfide borane complex; potassium carbonate; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; 3: Suzuki coupling;

DOI:10.1021/jm0002836

upstream raw materials:

4-cyanophenylboronic acid

propane-2-sulfonic acid (2-(4-bromo-phenyl)-propyl)-amide

4-Bromophenylacetonitrile

2-(4-Bromophenyl)propionitrile

Refernces

• 1、 -. "(BIS)sulfonamide derivatives". . . Retrieved 2008/06/13.
• 2、 Ornstein,Zimmerman,Arnold,Bleisch,Cantrell,Simon,Zarrinmayeh,Baker,Gates,Tizzano,Bleakman,Mandelzys,Jarvie,Ho,Deverill,Kamboj. "Biarylpropylsulfonamides as novel, potent potentiators of 2-amino-3-(5-methyl-3-hydroxyisoxazol-4-yl)-propanoic acid (AMPA) receptors [1]". . p. 4354 - 4358. Retrieved 2007/10/03.