Jump to content

PSB-SB-487: Difference between revisions

From Wikipedia, the free encyclopedia
Browse history interactively
← Previous edit
Content deleted Content added
VisualWikitext
mNo edit summary
auto mw
 
(3 intermediate revisions by 3 users not shown)
Line 1: Line 1:
{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| IUPAC_name = 7-(1,1-Dimethyloctyl)-5-hydroxy-3-(2-hydroxybenzyl)-2H-chromen-2-one
| IUPAC_name = 7-(1,1-Dimethyloctyl)-5-hydroxy-3-(2-hydroxybenzyl)-2''H''-chromen-2-one
| image = PSB-SB-487.svg
| image = PSB-SB-487.svg
| width = 300
| width = 300
Line 11: Line 12:
<!--Chemical data-->
<!--Chemical data-->
| C=26 | H=32 | O=4
| C=26 | H=32 | O=4
| molecular_weight = 408.53
| smiles = OC1=C(CC2=CC3=C(C=C(C(C)(C)CCCCCCC)C=C3O)OC2=O)C=CC=C1
| smiles = OC1=C(CC2=CC3=C(C=C(C(C)(C)CCCCCCC)C=C3O)OC2=O)C=CC=C1
| StdInChI = 1S/C26H32O4/c1-4-5-6-7-10-13-26(2,3)20-16-23(28)21-15-19(25(29)30-24(21)17-20)14-18-11-8-9-12-22(18)27/h8-9,11-12,15-17,27-28H,4-7,10,13-14H2,1-3H3
| StdInChI = 1S/C26H32O4/c1-4-5-6-7-10-13-26(2,3)20-16-23(28)21-15-19(25(29)30-24(21)17-20)14-18-11-8-9-12-22(18)27/h8-9,11-12,15-17,27-28H,4-7,10,13-14H2,1-3H3
Line 18: Line 18:
}}
}}


'''PSB-SB-487''' is a [[coumarin]] derivative which is an antagonist at the former [[orphan receptor]] [[GPR55]]. Unlike older GPR55 antagonists such as [[O-1918]], PSB-SB-487 has good selectivity over the related receptor [[GPR18]], with an IC<sub>50</sub> of 113nM at GPR55 vs 12500nM at GPR18.<ref>{{cite journal | vauthors = Rempel V, Volz N, Gläser F, Nieger M, Bräse S, Müller CE | title = Antagonists for the orphan G-protein-coupled receptor GPR55 based on a coumarin scaffold | journal = Journal of Medicinal Chemistry | volume = 56 | issue = 11 | pages = 4798–810 | date = June 2013 | pmid = 23679955 | doi = 10.1021/jm4005175 | url = https://figshare.com/articles/journal_contribution/Antagonists_for_the_Orphan_G_Protein_Coupled_Receptor_GPR55_Based_on_a_Coumarin_Scaffold/2405257 }}</ref> However it has poorer selectivity over other related receptors, acting as a weak antagonist at [[Cannabinoid receptor 1|CB<sub>1</sub>]] with a Ki of 1170nM, and a partial agonist at [[Cannabinoid receptor 2|CB<sub>2</sub>]] with a Ki of 292nM.<ref name="pmid22916707">{{cite journal | vauthors = Rempel V, Volz N, Hinz S, Karcz T, Meliciani I, Nieger M, Wenzel W, Bräse S, Müller CE | display-authors = 6 | title = 7-Alkyl-3-benzylcoumarins: a versatile scaffold for the development of potent and selective cannabinoid receptor agonists and antagonists | journal = Journal of Medicinal Chemistry | volume = 55 | issue = 18 | pages = 7967–77 | date = September 2012 | pmid = 22916707 | doi = 10.1021/jm3008213 }}</ref>
'''PSB-SB-487''' is a [[coumarin]] derivative which is an antagonist at the former [[orphan receptor]] [[GPR55]]. Unlike older GPR55 antagonists such as [[O-1918]], PSB-SB-487 has good selectivity over the related receptor [[GPR18]], with an IC<sub>50</sub> of 113nM at GPR55 vs 12500nM at GPR18.<ref>{{cite journal | vauthors = Rempel V, Volz N, Gläser F, Nieger M, Bräse S, Müller CE | title = Antagonists for the orphan G-protein-coupled receptor GPR55 based on a coumarin scaffold | journal = Journal of Medicinal Chemistry | volume = 56 | issue = 11 | pages = 4798–810 | date = June 2013 | pmid = 23679955 | doi = 10.1021/jm4005175 | url = https://figshare.com/articles/journal_contribution/2405257 }}</ref> However it has poorer selectivity over other related receptors, acting as a weak antagonist at [[Cannabinoid receptor 1|CB<sub>1</sub>]] with a Ki of 1170nM, and a partial agonist at [[Cannabinoid receptor 2|CB<sub>2</sub>]] with a Ki of 292nM.<ref name="pmid22916707">{{cite journal | vauthors = Rempel V, Volz N, Hinz S, Karcz T, Meliciani I, Nieger M, Wenzel W, Bräse S, Müller CE | display-authors = 6 | title = 7-Alkyl-3-benzylcoumarins: a versatile scaffold for the development of potent and selective cannabinoid receptor agonists and antagonists | journal = Journal of Medicinal Chemistry | volume = 55 | issue = 18 | pages = 7967–77 | date = September 2012 | pmid = 22916707 | doi = 10.1021/jm3008213 }}</ref>


== See also ==
== See also ==
Line 31: Line 31:


[[Category:Cannabinoids]]
[[Category:Cannabinoids]]
[[Category:Coumarins]]

Latest revision as of 04:24, 25 March 2024

PSB-SB-487
Identifiers
  • 7-(1,1-Dimethyloctyl)-5-hydroxy-3-(2-hydroxybenzyl)-2H-chromen-2-one
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H32O4
Molar mass408.538 g·mol−1
3D model (JSmol)
  • OC1=C(CC2=CC3=C(C=C(C(C)(C)CCCCCCC)C=C3O)OC2=O)C=CC=C1
  • InChI=1S/C26H32O4/c1-4-5-6-7-10-13-26(2,3)20-16-23(28)21-15-19(25(29)30-24(21)17-20)14-18-11-8-9-12-22(18)27/h8-9,11-12,15-17,27-28H,4-7,10,13-14H2,1-3H3
  • Key:YNWOMOUVWNKICO-UHFFFAOYSA-N

PSB-SB-487 is a coumarin derivative which is an antagonist at the former orphan receptor GPR55. Unlike older GPR55 antagonists such as O-1918, PSB-SB-487 has good selectivity over the related receptor GPR18, with an IC50 of 113nM at GPR55 vs 12500nM at GPR18.[1] However it has poorer selectivity over other related receptors, acting as a weak antagonist at CB1 with a Ki of 1170nM, and a partial agonist at CB2 with a Ki of 292nM.[2]

See also[edit]

References[edit]

  1. ^ Rempel V, Volz N, Gläser F, Nieger M, Bräse S, Müller CE (June 2013). "Antagonists for the orphan G-protein-coupled receptor GPR55 based on a coumarin scaffold". Journal of Medicinal Chemistry. 56 (11): 4798–810. doi:10.1021/jm4005175. PMID 23679955.
  2. ^ Rempel V, Volz N, Hinz S, Karcz T, Meliciani I, Nieger M, et al. (September 2012). "7-Alkyl-3-benzylcoumarins: a versatile scaffold for the development of potent and selective cannabinoid receptor agonists and antagonists". Journal of Medicinal Chemistry. 55 (18): 7967–77. doi:10.1021/jm3008213. PMID 22916707.
Retrieved from "https://en.wikipedia.org/w/index.php?title=PSB-SB-487&oldid=1215441594"