Penfluridol

Base Information

• Chemical Name: Penfluridol
• CAS No.: 26864-56-2
• Molecular Formula: C28H27ClF5NO
• Molecular Weight: 523.973
• Hs Code.: 29333990
• European Community (EC) Number: 248-074-5
• NSC Number: 759179
• UNII: 25TLU22Q8H
• DSSTox Substance ID: DTXSID5049021
• Nikkaji Number: J9.798E
• Wikipedia: Penfluridol
• Wikidata: Q2149707
• NCI Thesaurus Code: C90843
• Pharos Ligand ID: LUWP8QGGVYLG
• Metabolomics Workbench ID: 154571
• ChEMBL ID: CHEMBL47050
• Mol file: 26864-56-2.mol

Synonyms:Penfluridol;R 16341;R-16341;R16341;Semap

Chemical Property of Penfluridol

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 1.17E-14mmHg at 25°C
• Melting Point: 105-107 °C
• Refractive Index: 1.552
• Boiling Point: 587.7 °C at 760 mmHg
• PKA: 13.49±0.20(Predicted)
• Flash Point: 309.2 °C
• PSA: 23.47000
• Density: 1.29 g/cm³
• LogP: 7.47060
• Storage Temp.: 2-8°C
• Solubility.: H2O: insoluble
• XLogP3: 7.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 523.1701330
• Heavy Atom Count: 36
• Complexity: 647

Purity/Quality:

99% ^*data from raw suppliers

Penfluridol >98.0%(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CN(CCC1(C2=CC(=C(C=C2)Cl)C(F)(F)F)O)CCCC(C3=CC=C(C=C3)F)C4=CC=C(C=C4)F
• Recent EU Clinical Trials: Effectiveness of penfluridol (oral long acting neuroleptic) as compared to second generation oral neuroleptics in psychotic disorder patients: an open label randomized controlled trial.
• Uses: antineoplastic In terms of pharmacological action, penfluridol is similar to pimozide; however, it is significantly longer lasting, which is connected to the slow metabolism of the drug. Penfluridol is used as a supportive therapy in ambulatory settings for patients suffering from schizophrenia as well as patients with paranoid, psychotic, and neuroleptic conditions. Penfluridol has been used as an antipsychotic agent:to study its antimetastatic effect on triple-negative breast cancer cellsto study its effects on the growth of glioblastoma cell lines,to study its effects on the vascular endothelial growth factor (VEGF)-induced angiogenesis in human umbilical vein endothelial cells (HUVECs)
• Therapeutic Function: Antipsychotic

Technology Process of Penfluridol

There total 28 articles about Penfluridol 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: 98.1%

4-[4-chloro-3-trifluoromethylphenyl]-4-piperidinol (21928-50-7) + C23H22F2O3S → penfluridol (26864-56-2)

Guidance literature:

With potassium carbonate; In acetonitrile; at 50 - 60 ℃; for 15h; Inert atmosphere;

Reference yield: 91.3%

4-[4-chloro-3-trifluoromethylphenyl]-4-piperidinol (21928-50-7) + methanesulfonic acid 4,4-bis-(4-fluorophenyl)butyl ester → penfluridol (26864-56-2)

Guidance literature:

With potassium carbonate; In acetonitrile; at 50 - 60 ℃; for 0.2h; Inert atmosphere;

Reference yield: 81.5%

1-[4,4-bis(4-fluorophenyl)butyryl]-4-(3-trifluoromethyl-4-chlorophenyl)-4-piperidinol (50830-38-1) → penfluridol (26864-56-2)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 38 ℃; for 6h;

upstream raw materials:

4-[4-chloro-3-trifluoromethylphenyl]-4-piperidinol

4,4'-(4-bromobutane-1,1-diyl)bis(fluorobenzene)

4,4-bis(4-fluorophenyl)butan-1-ol

1,1-bis(4-fluorophenyl)prop-2-yn-1-ol

Downstream raw materials:

N-(1-(4,4-bis(4-fluorophenyl)butyl)-4-(4-chloro-3-(trifluoromethyl)phenyl)piperidin-4-yl)acetamide

1-(4,4-bis(4-fluorophenyl)butyl)-4-(4-chloro-3-(trifluoromethyl)phenyl)piperidin-4-yl acetate

penfluoridol decanoate

1-<4,4-Bis(4-fluorophenyl)butyl>-4-(4-chloro-3-trifluoromethylphenyl)-4-piperidyl 3,4,5-Trimethoxybenzoate

Refernces

• 1、 Gra?l, Simon,Chen, Yi-Hung,Hamze, Clémence,Tüllmann, Carl Phillip,Knochel, Paul. "Late Stage Functionalization of Secondary Amines via a Cobalt-Catalyzed Electrophilic Amination of Organozinc Reagents". . p. 494 - 497. Retrieved 2019/01/14.
• 2、 Chen, Gang,Xia, Hongguang,Cai, Yu,Ma, Dawei,Yuan, Junying,Yuan, Chengye. "Synthesis and SAR study of diphenylbutylpiperidines as cell autophagy inducers". scheme or table. p. 234 - 239. Retrieved 2011/02/26.