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Setoperone: Difference between revisions

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| verifiedrevid = 449587261 | verifiedrevid = 449587261
| ImageFile=Setoperone.svg | ImageFile=Setoperone.svg
| ImageClass = skin-invert-image
| ImageSize=250px | ImageSize=250px
| PIN=6-{2-ethyl}-7-methyl-2,3-dihydro-5''H''-thiazolopyrimidin-5-one | PIN=6-{2-ethyl}-7-methyl-2,3-dihydro-5''H''-thiazolopyrimidin-5-one
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}}</ref> }}</ref>
==Synthesis== ==Synthesis==
</ref> Patent (Intermediate 11 & Ex 1):<ref>EP0070053 idem Ludo E. J. Kennis, Josephus C. Mertens, {{US patent|4443451}} (1984 to Janssen Pharmaceutica N.V.).</ref> Radiolabelled:<ref>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.</ref>]] </ref> Patent (Intermediate 11 & Ex 1):<ref>EP0070053 idem Ludo E. J. Kennis, Josephus C. Mertens, {{US patent|4443451}} (1984 to Janssen Pharmaceutica N.V.).</ref> Radiolabelled:<ref>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.</ref>]]


The starting material is called 6-(2-hydroxyethyl)-7-methyl-2,3-dihydro-thiazolopyrimidin-5-one, ('''1'''). Halogenation of this with hydrobromic acid in acetic acid gives ('''2'''). Sn2 alkylation with 4-(4-fluorobenzoyl)piperidine ('''3''') under Finkelstein reaction conditions affords setoperone ('''4'''). The starting material is called 6-(2-hydroxyethyl)-7-methyl-2,3-dihydro-thiazolopyrimidin-5-one, ('''1'''). Halogenation of this with hydrobromic acid in acetic acid gives ('''2'''). Sn2 alkylation with 4-(4-fluorobenzoyl)piperidine ('''3''') under Finkelstein reaction conditions affords setoperone ('''4''').
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Latest revision as of 03:52, 14 January 2025

Setoperone
Names
Preferred IUPAC name 6-{2-ethyl}-7-methyl-2,3-dihydro-5H-thiazolopyrimidin-5-one
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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,6-13H2,1H3Key: RBGAHDDQSRBDOG-UHFFFAOYSA-N
  • 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,6-13H2,1H3Key: RBGAHDDQSRBDOG-UHFFFAOYAH
SMILES
  • CC1=C(C(=O)N2CCSC2=N1)CCN3CCC(CC3)C(=O)C4=CC=C(C=C4)F
Properties
Chemical formula C21H24FN3O2S
Molar mass 401.50 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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 or schizophrenia.

Synthesis

Synthesis: Patent (Intermediate 11 & Ex 1): Radiolabelled:

The starting material is called 6-(2-hydroxyethyl)-7-methyl-2,3-dihydro-thiazolopyrimidin-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 (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 [F]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 [F]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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