Resatorvid

Base Information

• Chemical Name: Resatorvid
• CAS No.: 243984-11-4
• Molecular Formula: C15H17ClFNO4S
• Molecular Weight: 361.822
• Hs Code.: 2935909099
• European Community (EC) Number: 897-524-2
• UNII: H2MZ648C31
• ChEMBL ID: CHEMBL225157
• DSSTox Substance ID: DTXSID00947269
• Metabolomics Workbench ID: 149595
• NCI Thesaurus Code: C87682
• Nikkaji Number: J2.258.881H
• Pharos Ligand ID: 2TCTF6SYX3C2
• Wikidata: Q27088534
• Wikipedia: Resatorvid
• Mol file: 243984-11-4.mol

Synonyms:CLI 095;CLI-095;CLI095;ethyl (6R)-6-(N-(2-chloro-4-fluorophenyl)sulfamoyl)cyclohex-1-ene-1-carboxylate;ethyl 6-(N-(2-chloro-4-fluorophenyl)sulfamoyl)cyclohex-1-ene-1-carboxylate;ethyl CFSCC;resatorvid;TAK 242;TAK-242;TAK242

Chemical Property of Resatorvid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 68-69 °C
• Refractive Index: 1.574
• Boiling Point: 461.958 °C at 760 mmHg
• PKA: 7.08±0.40(Predicted)
• Flash Point: 233.184 °C
• PSA: 80.85000
• Density: 1.39 g/cm³
• LogP: 4.41660
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: insoluble in H2O; ≥100.6 mg/mL in EtOH; ≥18.09 mg/mL in DMSO
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 361.0550851
• Heavy Atom Count: 23
• Complexity: 560

Purity/Quality:

99% ^*data from raw suppliers

Resatorvid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CCCCC1S(=O)(=O)NC2=C(C=C(C=C2)F)Cl
• Isomeric SMILES: CCOC(=O)C1=CCCC[C@H]1S(=O)(=O)NC2=C(C=C(C=C2)F)Cl
• Recent ClinicalTrials: TAK-242 in Patients With Acute Alcoholic Hepatitis
• Recent EU Clinical Trials: A Randomized, Double-Blind, Placebo-Controlled, Multicenter, Proof-of-Concept, Phase 2a Study to Evaluate the Efficacy, Safety, Pharmacokinetics, and Pharmacodynamics of Intravenous TAK-242 in Subjects With Acute Alcoholic Hepatitis Causing Decompensation of Alcohol related Cirrhosis and Acute-on-Chronic Liver Failure
• Uses: Resatorvid is a novel selective Toll-like receptor 4 signal transduction inhibitor. Resatorvid inhibits various kinds of inflammatory mediators such as nitric oxide (NO), tumor necrosis factor (TNF)-α , interleukin (IL)-1, IL-6, IL-10, macrophage inhibitory protein (MIP)-2 and prostaglandin E2 from lipopolysaccharide (LPS)-stimulated macrophages. Resatorvid is a novel selective Toll-like receptor 4 signal transduction inhibitor. Resatorvid inhibits various kinds of inflammatory mediators such as nitric oxide (NO), tumor necrosis factor (TNF)-α, interleukin (IL)-1, IL-6, IL-10, macrophage inhibitory protein (MIP)-2 and prostaglandin E2 from lipopolysaccharide (LPS)-stimulated macrophages.

Technology Process of Resatorvid

There total 17 articles about Resatorvid 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: 72.0%

(6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylic acid (890155-18-7) + ethanol (64-17-5) → ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate (243984-11-4,243984-10-3)

Guidance literature:

With sulfuric acid; for 19h; Heating;

DOI:10.1248/cpb.54.58

Reference yield: 68.0%

ethyl (6R)-6-{[[(2S)-2-(acetyloxy)-2-phenylacetyl]-(2-chloro-4-fluorophenyl)amino]sulfonyl}cyclohex-1-ene-1-carboxylate (415679-88-8) → ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate (243984-11-4,243984-10-3) + acetic acid (2-chloro-4-fluoro-phenylcarbamoyl)-phenyl-methyl ester

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1016/j.tet.2007.02.127

Reference yield: 68.0%

→ ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate (243984-11-4,243984-10-3)

Guidance literature:

upstream raw materials:

ethyl (6RS)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate

(6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylic acid

ethanol

acetoxymethyl (6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate

Refernces

• 1、 -. "SUBSTITUTED CYCLOHEXENES". Page/Page column 66. . Retrieved 2009/03/07.
• 2、 Yamada,Ichikawa,Yamano,Kikumoto,Nishikimi,Tamura,Kitazaki. "Optically active cyclohexene derivative as a new antisepsis agent: An efficient synthesis of ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl)-sulfamoyl] cyclohex-1-ene-1-carboxylate (TAK-242)". . p. 58 - 62. Retrieved 2007/10/03.