26864-56-2 Usage
Description
Penfluridol is an antipsychotic drug that is structurally related to pimozide and is characterized by its long-lasting effects due to its slow metabolism. It is known for its antimetastatic properties and its ability to inhibit the growth of certain cancer cells, as well as its effects on vascular endothelial growth factor (VEGF)-induced angiogenesis.
Uses
Used in Pharmaceutical Industry:
Penfluridol is used as an antipsychotic agent for the treatment of schizophrenia, paranoid, psychotic, and neuroleptic conditions in patients. Its long-lasting effects make it suitable for supportive therapy in ambulatory settings.
Used in Anticancer Applications:
Penfluridol is used as an antineoplastic agent to study its antimetastatic effects on triple-negative breast cancer cells, its effects on the growth of glioblastoma cell lines, and its impact on VEGF-induced angiogenesis in human umbilical vein endothelial cells (HUVECs).
Brand Name:
Semap (Ortho-McNeil) is the brand name under which Penfluridol is marketed.
Originator
Semap,Janssen-Le Brun ,W. Germany ,1975
Manufacturing Process
A mixture of 24 parts of 4,4-bis(p-fluorophenyl)butyl chloride, 20.9 parts of 4(4-chloro-α,α,α-trifluoro-m-tolyl)-4-piperidinol, 13.8 parts of sodium carbonate, a few crystals of potassium iodide in 600 parts of 4-methyl-2pentanone is stirred and refluxed for 60 hours. The reaction mixture is cooled and 150 parts of water is added. The organic layer is separated, dried, filtered and evaporated. The oily residue is crystallized from diisopropylether, yielding 4-(4chloro-α,α,α-trifluoro-m-tolyl)-1-[4,4-bis(p-fiuorophenyl)butyl]-4piperidinol; melting point 106.5°C.
Therapeutic Function
Antipsychotic
Biochem/physiol Actions
Penfluridol is studied in the treatment of schizophrenia, Tourette syndrome and acute psychosis. It also exhibits anticancer activity.
Safety Profile
Poison by ingestion and intravenous routes. Experimental teratogenic and reproductive effects. A neuroleptic agent. When heated to decomposition it emits very toxic fumes of Cl-, F-, and NOx.
Synthesis
Penfluridol, 4-(4-chloro-3-trifluoromethylphenyl)-1-[4,4-bis-(p-fluorophenyl)
butyl]-4-piperidinol (6.6.12), is synthesized implementing a Grignard reaction between
1-carbomethoxypiperidin-4-one and 4-chloro-3-trifluoromethylphenylmagnesium bromide,
giving 1-carbomethoxy-(4-chloro-3-trifluoromethylphenyl)-4-piperidinol (6.6.10). Upon
alkaline hydrolysis of the carbomethoxy group, it turns into (4-chloro-3-trifluoromethylphenyl)-4-piperidinol (6.6.11), the alkylation of which with 1,1-bis(4-fluorophenyl)butyl bromide (6.6.3) gives penfluridol (6.6.12) [67–69].
Check Digit Verification of cas no
The CAS Registry Mumber 26864-56-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,6,8,6 and 4 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 26864-56:
(7*2)+(6*6)+(5*8)+(4*6)+(3*4)+(2*5)+(1*6)=142
142 % 10 = 2
So 26864-56-2 is a valid CAS Registry Number.
InChI:InChI=1/C28H27ClF5NO/c29-26-12-7-21(18-25(26)28(32,33)34)27(36)13-16-35(17-14-27)15-1-2-24(19-3-8-22(30)9-4-19)20-5-10-23(31)11-6-20/h3-12,18,24,36H,1-2,13-17H2
26864-56-2Relevant articles and documents
Improved method for preparing penfuridol
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, (2020/06/09)
The invention discloses an improved method for preparing penfuridol, comprising the following steps: using 4, 4-bis (4-fluorophenyl) butyric acid as a starting material, carrying out reduction synthesis to synthesize an intermediate I [4, 4-bis (4-fluorophenyl)-1-butanol]; carrying out esterification with a sulfonyl chloride compound to synthesize an intermediate II [4, 4-bis (4-fluorophenyl)-1 (4-methyl-phenyl)-butyl sulfonate] or [4, 4-bis (4-fluorophenyl)-1-methyl-butyl sulfonate]; and condensing with pipradrol to obtain penfuridol. According to the preparation method, 4, 4-bis (4-fluorophenyl) butyric acid is used as a raw material, penfuridol is obtained through a reduction reaction, an esterification reaction and a condensation reaction, the total yield is 81.3%, the whole process isconvenient to operate and mild in reaction, the obtained product is high in yield and purity, and the preparation method is more economical and more suitable for industrial application. The technicalproblems that an existing method is low in yield and poor in purity are solved. The reaction general formula is as shown in the specification.
Penfluridol preparation method
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, (2017/02/24)
The invention discloses a penfluridol preparation method. The penfluridol preparation method includes the following steps of 1), subjecting succinic anhydride and fluorobenzene to Friedel-Crafts reaction prior to acid decomposition, and collecting a compound from the formula 2) as is shown in the description; 2), putting the compound in a solvent to collect a compound in formula 3) as is shown in the description in a solvent reduced through a reducing agent; 3), putting the compound into the fluorobenzene to perform the Friedel-Crafts reaction to collect a compound in the formula 4) as is shown in the description; subjecting the compound and ethyl chloroformate to action to generate a compound in formula 5) as is shown in the description; 5), subjecting the compound and a compound shown in formula (XVII) to reaction prior to hydrolyzation to collect a compound in formula 6) as is shown in the description; 6), performing reduction with the reducing agent prior to hydrolyzing a reduction product and then collecting penfluridol (I). The penfluridol preparation method is high in yield, low in cost, moderate in reaction condition, short in circuit, proper for industrial production, low in three wastes, easy to treat and suitable for industrial production.
DIPHENYLBUTYPIPERIDINE AUTOPHAGY INDUCERS
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Page/Page column 7; 84-85, (2011/12/02)
Autophagy inducing compounds, methods of their preparation and use, and kits containg said compounds are disclosed herein.
