5-(1H-indol-3-ylmethyl)-3-methyl-2-thioxo-4-Imidazolidinone

Base Information

• Chemical Name: 5-(1H-indol-3-ylmethyl)-3-methyl-2-thioxo-4-Imidazolidinone
• CAS No.: 4311-88-0
• Molecular Formula: C13H13 N3 O S
• Molecular Weight: 259.332
• Hs Code.: 29339900
• DSSTox Substance ID: DTXSID40385186
• Nikkaji Number: J2.537.490H
• Wikidata: Q27163481
• Pharos Ligand ID: X4J7YJJQLLAA
• ChEMBL ID: CHEMBL195008
• Mol file: 4311-88-0.mol

Synonyms:Nec-1 compound;necrostatin-1

Chemical Property of 5-(1H-indol-3-ylmethyl)-3-methyl-2-thioxo-4-Imidazolidinone

Chemical Property:

• Vapor Pressure: 5.24E-08mmHg at 25°C
• Melting Point: 151℃
• Boiling Point: 441.9°Cat760mmHg
• PKA: 9.46±0.40(Predicted)
• Flash Point: 221.1°C
• PSA: 80.22000
• Density: 1.4g/cm³
• LogP: 1.69220
• Storage Temp.: −20°C
• Sensitive.: Light Sensitive
• Solubility.: DMSO: >10 mg/mL
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 259.07793322
• Heavy Atom Count: 18
• Complexity: 373

Purity/Quality:

99% ^*data from raw suppliers

Necrostatin-1 ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/39
• Safety Statements: 36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1C(=O)C(NC1=S)CC2=CNC3=CC=CC=C32
• Description: Necrostatin-1 is a specific RIP1 inhibitor and inhibits TNF-α-induced necroptosis with EC50 of 490 nM in 293T cells. Necrostatin-1 (4311-88-0) is an inhibitor of necroptosis (non-apoptotic cell death pathway; EC50 = 494 nM).1 It is an ATP-competitive death domain receptor-associated adaptor kinase (RIP1) inhibitor (EC50 = 182 nM).2 Necrostatin-1 displays a protective effect in a mouse model of ischemic brain injury1, inhibits myocardial cell death and reduces infarct size in various mouse heart models3 and inhibits glutamate-induced oxytosis in HT-22 cells4.
• Uses: Necrostatin-1 is a specific RIP1 inhibitor and inhibits TNF-α-induced necroptosis with EC50 of 490 nM. Necroptosis is a regulated caspase-independent cell death mechanism that results in morphological features resembling necrosis. Necrostatin-1 is an inhibitor of RIP1 kinase that prevents the death of TNF-α-treated FADD-deficient Jurkat cells. Necrostatin-1 has been used to investigate the pathological importance of necroptosis in ischemic brain injury and myocardial infarction. Necroptosis is a regulated caspase-independent cell death mechanism that results in morphological features resembling necrosis. Necrostatin-1 is an inhibitor of RIP1 kinase that prevents the death of TNF-α-treated FADD-deficient Jurkat cells. Necrostatin-1 has been used to investigate the pathological importance of necroptosis in ischemic brain injury and myocardial infarction.

Technology Process of 5-(1H-indol-3-ylmethyl)-3-methyl-2-thioxo-4-Imidazolidinone

There total 5 articles about 5-(1H-indol-3-ylmethyl)-3-methyl-2-thioxo-4-Imidazolidinone 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: 89.0%

methyl thioisocyanate (556-61-6) + DL-tryptophan methyl ester (7303-49-3) → necrostatin-1 (4311-88-0)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2005.07.077

Reference yield: 89.0%

DL-7-Fluoro-tryptophan methyl ester + methyl thioisocyanate (556-61-6) → necrostatin-1 (4311-88-0)

Guidance literature:

In dichloromethane; at 20 ℃; for 1h;

Reference yield:

3-(1H-indol-3-yl)-2-(3-methyl-thioureido)-propionic acid → necrostatin-1 (4311-88-0)

Guidance literature:

With hydrogenchloride; at 20 ℃; for 48h; pH=1;

DOI:10.1016/j.bmcl.2005.07.077

upstream raw materials:

methyl thioisocyanate

DL-tryptophan methyl ester

Trp

Refernces

• 1、 -. "Inhibitors of cellular necrosis". Page/Page column 31. . Retrieved 2008/06/13.