4-Chloro-N-[2-[[5-(trifluoromethyl)-2-pyridinyl]sulfonyl]ethyl]benzamide

Base Information

• Chemical Name: 4-Chloro-N-[2-[[5-(trifluoromethyl)-2-pyridinyl]sulfonyl]ethyl]benzamide
• CAS No.: 188591-46-0
• Molecular Formula: C₁₅H₁₂ClF₃N₂O₃S
• Molecular Weight: 392.786
• European Community (EC) Number: 662-808-5
• UNII: DD8MJ95LTV
• DSSTox Substance ID: DTXSID00384175
• Nikkaji Number: J3.456.344F
• Wikidata: Q72460469
• Pharos Ligand ID: S2FR38NR81WX
• ChEMBL ID: CHEMBL598608
• Mol file: 188591-46-0.mol

Synonyms:4-chloro-N-(2-((5-trifluoromethyl-2-pyridyl)sulfonyl)ethyl)benzamide;GSK 3787;GSK-3787;GSK3787

Chemical Property of 4-Chloro-N-[2-[[5-(trifluoromethyl)-2-pyridinyl]sulfonyl]ethyl]benzamide

Chemical Property:

• Boiling Point: 585.1±50.0 °C(Predicted)
• PKA: 12.92±0.46(Predicted)
• PSA: 84.51000
• Density: 1.448±0.06 g/cm3 (20 oC 760 Torr)
• LogP: 4.42920
• Storage Temp.: Store at +4°C
• Solubility.: DMSO: ≥10mg/mL
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 392.0209256
• Heavy Atom Count: 25
• Complexity: 557

Purity/Quality:

98%,99%, ^*data from raw suppliers

GSK 3787 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(=O)NCCS(=O)(=O)C2=NC=C(C=C2)C(F)(F)F)Cl
• Description: GSK-3787 (188591-46-0) is a selective and irreversible antagonist of the peroxisome proliferator-activated receptor δ (PPARδ) – plC50 = 6.6. It covalently binds to Cys 249 in the PPARd binding site.
• Uses: PPARβ/δ is thought to play a role in lipid homeostasis and glucose disposal by regulating genes involved in fatty acid oxidation, reverse cholesterol transport, and carbon substrate utilization in skeletal muscle. It has also been implicated in the progression of certain cancers. GSK3787 is an irreversible antagonist of PPARβ/δ (pIC50 = 6.6) with no measurable affinity for PPARα or PPARγ (pIC50 >5). At 1μM, it inhibits the expression of PPARβ/δ-regulated target genes, pyruvate dehydrogenase kinase 4 and carnitine palmitoyl transferase 1a, which are important for energy homeostasis in human skeletal muscle cells. GSK3787 (at 1 μM) also antagonizes agonist-induced expression of angiopoietin-like protein 4 in mouse fibroblasts, mouse keratinocytes, and human MCF-7, Huh7, and HepG2 cancer cell lines.[Cayman Chemical] GSK3787 has been used to inhibit the role of peroxisome proliferator-activated receptor-delta (PPARδ), during the pre-implantation period of bovine embryonic development. It has also been used as a PPARδ-specific inhibitor in in vitro maturation (IVM) media to inhibit PPARδ.

Technology Process of 4-Chloro-N-[2-[[5-(trifluoromethyl)-2-pyridinyl]sulfonyl]ethyl]benzamide

There total 1 articles about 4-Chloro-N-[2-[[5-(trifluoromethyl)-2-pyridinyl]sulfonyl]ethyl]benzamide 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:

(2-{[5-(trifluoromethyl)-2-pyridyl]sulfonyl}ethyl)amine hydrochloride + 4-chloro-benzoyl chloride (122-01-0) → GSK3787 (188591-46-0)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1021/jm900464j

upstream raw materials:

4-chloro-benzoyl chloride

Refernces