Siramesine

Base Information

• Chemical Name: Siramesine
• CAS No.: 147817-50-3
• Molecular Formula: C30H31 F N2 O
• Molecular Weight: 454.587
• UNII: 3IX8CWR24V
• DSSTox Substance ID: DTXSID90163810
• Nikkaji Number: J670.035G
• Wikipedia: Siramesine
• Wikidata: Q7529961
• NCI Thesaurus Code: C73302
• Pharos Ligand ID: Z6ZR2RR2ST4F
• Metabolomics Workbench ID: 149832
• ChEMBL ID: CHEMBL61479
• Mol file: 147817-50-3.mol

Synonyms:1-(4-fluorophenyl)-3-(4-(4-(4-fluorophenyl)-1-piperidinyl)-1-butyl)-1H-indole;Lu 28-179;Lu-28-179;Siramesine

Chemical Property of Siramesine

Chemical Property:

• Boiling Point: 611.4±55.0 °C(Predicted)
• PKA: 9.45±0.20(Predicted)
• PSA: 17.40000
• Density: 1.19±0.1 g/cm3(Predicted)
• LogP: 6.55170
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Soluble in DMSO (up to at least 25 mg/ml)
• XLogP3: 6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 454.24204178
• Heavy Atom Count: 34
• Complexity: 656

Purity/Quality:

99% ^*data from raw suppliers

1'-(4-(1-(4-Fluorophenyl)-1H-indol-3-yl)butyl)-3H-spiro[isobenzofuran-1,4'-piperidine] 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCC12C3=CC=CC=C3CO2)CCCCC4=CN(C5=CC=CC=C54)C6=CC=C(C=C6)F
• Description: Siramesine (Lu 28-179, 147817-50-3) is a σ2 selective agonist?(IC50’s: σ1 = 17nM, σ2 = 0.2nM).1?It produced non-sedating potent and long-last anxiolytic effects in rodents.2?Siramesine induced caspase-independent programmed cell death in various cancer cell lines?via?increased levels of ROS and lysosomal leakage.3,4,5?Mitochondrial destabilization via loss of membrane potential and increased ROS has also been offered as a mechanism of action for the triggering of cell death by Siramesine.6
• Uses: Treatment of prostate cancer.

Technology Process of Siramesine

There total 8 articles about Siramesine 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: 66.0%

3H-spiro[2-benzofuran-1,4'-piperidine] (38309-60-3) + C18H17BrFN → siramesine (147817-50-3)

Guidance literature:

With potassium carbonate; In acetonitrile; Reflux;

DOI:10.1039/c5md00079c

Reference yield:

4-(1H-indol-3-yl)butan-1-ol (3364-37-2) → siramesine (147817-50-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 44 percent / CuI; ZnO; K₂CO₃ / 1-methyl-pyrrolidin-2-one / 160 °C

2: triethylamine / CH₂Cl₂ / 0 - 20 °C

3: Na₂CO₃ / H₂O; acetone / 50 °C

With copper(l) iodide; sodium carbonate; potassium carbonate; triethylamine; zinc(II) oxide; In 1-methyl-pyrrolidin-2-one; dichloromethane; water; acetone; 1: Ullmann arylation reaction;

DOI:10.1002/jlcr.893

Reference yield:

4-indol-3-yl-butyric acid (133-32-4) → siramesine (147817-50-3)

Guidance literature:

Multi-step reaction with 4 steps

1: LiAlH₄ / tetrahydrofuran / 4 h / 20 °C

2: 44 percent / CuI; ZnO; K₂CO₃ / 1-methyl-pyrrolidin-2-one / 160 °C

3: triethylamine / CH₂Cl₂ / 0 - 20 °C

4: Na₂CO₃ / H₂O; acetone / 50 °C

With copper(l) iodide; lithium aluminium tetrahydride; sodium carbonate; potassium carbonate; triethylamine; zinc(II) oxide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; dichloromethane; water; acetone; 2: Ullmann arylation reaction;

DOI:10.1002/jlcr.893

upstream raw materials:

3H-spiro[2-benzofuran-1,4'-piperidine]

4-<1-(4-fluorophenyl)-1H-indol-3-yl>-1-butanol methanesulfonate ester

4-(1H-indol-3-yl)butan-1-ol

4-indol-3-yl-butyric acid

Refernces

• 1、 Wuest, Frank R.,Kniess, Torsten. "N-Arylation of indoles with 4-[18F]fluoroiodobenzene: Synthesis of 18F-labelled σ2 receptor ligands for positron emission tomography (PET)". . p. 31 - 43. Retrieved 2007/10/03.
• 2、 -. "Piperidine derivatives having anxiolytic effect". . . Retrieved 2008/06/13.