N-((1,2,3,5,6,7-hexahydro-s-indacen-4-yl)carbamoyl)-4-(2-hydroxypropan-2-yl)furan-2-sulfonamide

Base Information

• Chemical Name: N-((1,2,3,5,6,7-hexahydro-s-indacen-4-yl)carbamoyl)-4-(2-hydroxypropan-2-yl)furan-2-sulfonamide
• CAS No.: 210826-40-7
• Molecular Formula: C₂₀H₂₄N₂O₅S
• Molecular Weight: 404.487
• UNII: 6RS86E2BWQ
• DSSTox Substance ID: DTXSID2047301
• Nikkaji Number: J1.919.729H
• Wikidata: Q27083691
• Pharos Ligand ID: PAJSKZHFS3DB
• ChEMBL ID: CHEMBL3183703
• Mol file: 210826-40-7.mol

Synonyms:2-Furansulfonamide, N-(((1,2,3,5,6,7-hexahydro-s-indacen-4-yl)amino)carbonyl)-4-(1-hydroxy-1-methylethyl)-;CP-456,773;CP-456773;CRID3;MCC-950;MCC950;N-(1,2,3,5,6,7-Hexahydro-s-indacen-4-ylcarbamoyl)-4-(2-hydroxy-2-propanyl)-2-furansulfonamide

Chemical Property of N-((1,2,3,5,6,7-hexahydro-s-indacen-4-yl)carbamoyl)-4-(2-hydroxypropan-2-yl)furan-2-sulfonamide

Chemical Property:

• Melting Point: 239 °C
• PKA: 4.74±0.10(Predicted)
• PSA: 117.02000
• Density: 1.396±0.06 g/cm3(Predicted)
• LogP: 4.53950
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (up to 40 mg/ml) or in Water (up to 30 mg/ml)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 404.14059304
• Heavy Atom Count: 28
• Complexity: 684

Purity/Quality:

99% ^*data from raw suppliers

MCC-950 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C1=COC(=C1)S(=O)(=O)NC(=O)NC2=C3CCCC3=CC4=C2CCC4)O
• Description: MCC-950 (210826-40-7) was originally found to act as a cytokine release inhibitory drug (CRID), arresting activated monocytes and preventing activation of caspase-1.1?Discovered to be a novel inhibitor of the NLRP3 and AIM2 inflammasomes.2?MCC-950 blocks canonical and noncanonical NLRP3 activation at nanomolar concentrations.3?Inhibits interleukin 1β (IL-1β) secretion?in vivo?and attenuates the severity of experimental autoimmune encephalomyelitis (an MS disease model).3?Disrupts the interaction between AIM2 and ASC in a reconstituted cell-free inflammasome.4?MCC-950 is a valuable new tool for exploring the pathophysiology of NLRP3.
• Uses: MCC950 selectively inhibits pyrin domain-containing protein 3 (NLRP3) inflammasome, a protein complex involved in the inflammatory process (1). The NLRP3 inflammasome is related to a wide range of immune disorders such as multiple sclerosis, inflammatory bowel disease, auto-immune and auto-inflammatory diseases (2). MCC950 has been shown to specifically inhibit the activation of NLRP3 but not the AIM2, NLRC4 or NLRP1 inflammasomes (1). MCC950 is a potential therapeutic for NLRP3-associated syndromes.

Technology Process of N-((1,2,3,5,6,7-hexahydro-s-indacen-4-yl)carbamoyl)-4-(2-hydroxypropan-2-yl)furan-2-sulfonamide

There total 8 articles about N-((1,2,3,5,6,7-hexahydro-s-indacen-4-yl)carbamoyl)-4-(2-hydroxypropan-2-yl)furan-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: 63.0%

4-isocyanato-1,2,3,5,6, 7-hexahydro-s-indacene (210827-31-9) + 4-(1-Hydroxy-1-methyl-ethyl)-furan-2-sulfonamide (210827-34-2) → MCC950 (210826-40-7)

Guidance literature:

4-(1-Hydroxy-1-methyl-ethyl)-furan-2-sulfonamide; With sodium methylate; In methanol;

4-isocyanato-1,2,3,5,6, 7-hexahydro-s-indacene; at 20 ℃; Reflux;

Reference yield:

1,2,3,5,6,7-hexahydro-s-indacen-4-yl-amine (63089-56-5) → MCC950 (210826-40-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 80 g / Et₃N / tetrahydrofuran / 4 h / Heating

2.1: MeONa / tetrahydrofuran

2.2: 4.9 g / tetrahydrofuran / 4 h / Heating

3.1: 8.33 g / aq. HCl

With hydrogenchloride; sodium methylate; triethylamine; In tetrahydrofuran;

DOI:10.1081/SCC-120021029

Reference yield:

INDANE (496-11-7) → MCC950 (210826-40-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 78 percent / AlCl₃ / CH₂Cl₂ / -10 - 20 °C

2.1: H₂SO₄ / 48 h / 55 - 60 °C

3.1: HNO₃; H₂SO₄ / 2 h / 0 - 5 °C

3.2: 8.8 kg / methanesulfonic acid; H₂ / palladium hydroxide on carbon / methanol; H₂O / 9 h / 2585.74 Torr

4.1: 80 g / Et₃N / tetrahydrofuran / 4 h / Heating

5.1: MeONa / tetrahydrofuran

5.2: 4.9 g / tetrahydrofuran / 4 h / Heating

6.1: 8.33 g / aq. HCl

With hydrogenchloride; aluminium trichloride; sulfuric acid; nitric acid; sodium methylate; triethylamine; In tetrahydrofuran; dichloromethane; 1.1: Friedel-Crafts acylation;

DOI:10.1081/SCC-120021029

upstream raw materials:

INDANE

3,5,6,7-tetrahydro-2H-s-indacen-1-one

3-chloro-1-(2,3-dihydro-1H-inden-5-yl)propan-1-one

1,2,3,5,6,7-hexahydro-s-indacen-4-yl-amine

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