SCH-442,416

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SCH-442,416
SCH-422,416 Structure.svg
Names
Preferred IUPAC name
2-(Furan-2-yl)-7-[3-(4-methoxyphenyl)propyl]-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine
Other names
SCH-442,416
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C20H19N7O2/c1-28-14-8-6-13(7-9-14)4-2-10-26-18-15(12-22-26)19-23-17(16-5-3-11-29-16)25-27(19)20(21)24-18/h3,5-9,11-12H,2,4,10H2,1H3,(H2,21,24) Yes check.svgY
    Key: AEULVFLPCJOBCE-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C20H19N7O2/c1-28-14-8-6-13(7-9-14)4-2-10-26-18-15(12-22-26)19-23-17(16-5-3-11-29-16)25-27(19)20(21)24-18/h3,5-9,11-12H,2,4,10H2,1H3,(H2,21,24)
    Key: AEULVFLPCJOBCE-UHFFFAOYAA
  • n1n3c(nc4c(c3nc1c2occc2)cnn4CCCc5ccc(OC)cc5)N
Properties
C20H19N7O2
Molar mass 389.410
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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SCH-442,416 is a highly selective adenosine A2a subtype receptor antagonist. It is widely used in its 11C radiolabelled form to map the distribution of A2a receptors in the brain, where they are mainly found in the striatum, nucleus accumbens, and olfactory tubercle. [1] Given its distribution in the brain, A2a receptors have been investigated for the treatment of various neurological disorders, and SCH-442,416 has shown promise in treatment of depression, [2] Parkinson's disease, [3] and catalepsy. [4]

References

  1. ↑ Moresco RM, Todde S, Belloli S, Simonelli P, Panzacchi A, Rigamonti M, et al. (April 2005). "In vivo imaging of adenosine A2A receptors in rat and primate brain using [11C]SCH442416". European Journal of Nuclear Medicine and Molecular Imaging. 32 (4): 405–13. doi:10.1007/s00259-004-1688-5. PMID   15549298. S2CID   20909406.
  2. ↑ El Yacoubi M, Costentin J, Vaugeois JM (December 2003). "Adenosine A2A receptors and depression". Neurology. 61 (11 Suppl 6): S82-7. doi:10.1212/01.wnl.0000095220.87550.f6. PMID   14663017. S2CID   36219448.
  3. ↑ Matsuya T, Takuma K, Sato K, Asai M, Murakami Y, Miyoshi S, et al. (March 2007). "Synergistic effects of adenosine A2A antagonist and L-DOPA on rotational behaviors in 6-hydroxydopamine-induced hemi-Parkinsonian mouse model". Journal of Pharmacological Sciences. 103 (3): 329–32. doi: 10.1254/jphs.scz070058 . PMID   17341841.
  4. ↑ Mihara T, Noda A, Arai H, Mihara K, Iwashita A, Murakami Y, et al. (July 2008). "Brain adenosine A2A receptor occupancy by a novel A1/A2A receptor antagonist, ASP5854, in rhesus monkeys: relationship to anticataleptic effect". Journal of Nuclear Medicine. 49 (7): 1183–8. doi: 10.2967/jnumed.108.051474 . PMID   18552135.
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