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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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

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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.