Setoperone

Last updated
Setoperone
Setoperone.svg
Names
Preferred IUPAC name
6-{2-[4-(4-Fluorobenzoyl)piperidin-1-yl]ethyl}-7-methyl-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one
Identifiers
3D model (JSmol)
ChemSpider
KEGG
PubChem CID
UNII
  • 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 X mark.svgN
    Key: RBGAHDDQSRBDOG-UHFFFAOYSA-N X mark.svgN
  • InChI=1/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
    Key: RBGAHDDQSRBDOG-UHFFFAOYAH
  • CC1=C(C(=O)N2CCSC2=N1)CCN3CCC(CC3)C(=O)C4=CC=C(C=C4)F
Properties
C21H24FN3O2S
Molar mass 401.50 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Setoperone is a compound that is a ligand to the 5-HT2A receptor. 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 [1] or schizophrenia. [2]

Contents

Synthesis

Synthesis: Patent (Intermediate 11 & Ex 1): Radiolabelled: Setoperone synthesis.svg
Synthesis: Patent (Intermediate 11 & Ex 1): Radiolabelled:

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

  1. ↑ Jeffrey H. Meyer, Shitij Kapur, Sylvain Houle, Jean DaSilva, Beata Owczarek, Gregory M. Brown, Alan A. Wilson and Sidney H. Kennedy (July 1, 1999). "Prefrontal Cortex 5-HT2 Receptors in Depression: An [18F]Setoperone PET Imaging Study" . American Journal of Psychiatry . 156 (7): 1029–1034. doi:10.1176/ajp.156.7.1029. PMID   10401447. S2CID   453720.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. ↑ Ralph Lewis, Shitij Kapur, Corey Jones, Jean DaSilva, Gregory M. Brown, Alan A. Wilson, Sylvain Houle and Robert B. Zipursky (January 1, 1999). "Serotonin 5-HT2 Receptors in Schizophrenia: A PET Study Using [18F]Setoperone in Neuroleptic-Naive Patients and Normal Subjects". American Journal of Psychiatry . 156 (1): 72–78. doi:10.1176/ajp.156.1.72. PMID   9892300.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ↑ Drugs of the Future, 10, 1, 40 (1985).
  4. ↑ EP0070053 idem Ludo E. J. Kennis, Josephus C. Mertens, U.S. patent 4,443,451 (1984 to Janssen Pharmaceutica N.V.).
  5. ↑ Maziere, B.; Crouzel, C.; Venet, M.; Stulzaft, O.; Sanz, G.; Ottaviani, M.; Sejourne, C.; Pascal, O.; Bisserbe, J.C. (1988). "Synthesis, affinity and specificity of 18F-setoperone, a potential ligand for in-vivo imaging of cortical serotonin receptors". International Journal of Radiation Applications and Instrumentation. Part B. Nuclear Medicine and Biology. 15 (4): 463–468. doi:10.1016/0883-2897(88)90018-9.
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