Setoperone

Pharmaceutical compound From Wikipedia, the free encyclopedia

Setoperone (INNTooltip International Nonproprietary Name; USANTooltip United States Adopted Name; developmental code name R-52245) is a compound that is a ligand to the 5-HT2A receptor.[1] It can be radiolabeled with the radioisotope fluorine-18 and used as a radioligand with positron emission tomography (PET). Several research studies have used the radiolabeled setoperone in neuroimaging for the studying neuropsychiatric disorders, such as depression[2] or schizophrenia.[3] The drug was first described by at least 1984.[1]

Other namesR-52245; R52245
ATC code
  • None
Quick facts Clinical data, Other names ...
Setoperone
Clinical data
Other namesR-52245; R52245
Drug classSerotonin 5-HT2A receptor antagonist
ATC code
  • None
Identifiers
  • 6-{2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl}-7-methyl-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H24FN3O2S
Molar mass401.50 g·mol−1
3D model (JSmol)
  • CC1=C(C(=O)N2CCSC2=N1)CCN3CCC(CC3)C(=O)C4=CC=C(C=C4)F
  • InChI=1S/C21H24FN3O2S/c1-14-18(20(27)25-12-13-28-21(25)23-14)8-11-24-9-6-16(7-10-24)19(26)15-2-4-17(22)5-3-15/h2-5,16H,6-13H2,1H3 ☒N
  • Key:RBGAHDDQSRBDOG-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)
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Chemistry

Synthesis

Synthesis:[4] Radiolabelled:[5]

The starting material is called 6-(2-hydroxyethyl)-7-methyl-2,3-dihydro-[1,3]thiazolo[3,2-a]pyrimidin-5-one, CID:15586462 (1). Halogenation of this with hydrobromic acid in acetic acid gives CID:15586463 (2). Sn2 alkylation with 4-(4-fluorobenzoyl)piperidine [56346-57-7] (3) under Finkelstein reaction conditions affords setoperone (4).

See also

References

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