PSB-SB-487: Difference between revisions
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{{Short description|Chemical compound}} |
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{{Drugbox |
{{Drugbox |
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| IUPAC_name = 7-(1,1-Dimethyloctyl)-5-hydroxy-3-(2-hydroxybenzyl)- |
| IUPAC_name = 7-(1,1-Dimethyloctyl)-5-hydroxy-3-(2-hydroxybenzyl)-2''H''-chromen-2-one |
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| image = PSB-SB- |
| image = PSB-SB-487.svg |
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| width = 300 |
| width = 300 |
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<!--Clinical data--> |
<!--Clinical data--> |
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<!--Chemical data--> |
<!--Chemical data--> |
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| C=26 | H=32 | O=4 |
| C=26 | H=32 | O=4 |
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| molecular_weight = 408.53 |
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| 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 |
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| InChI = 1/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 |
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| InChIKey = YNWOMOUVWNKICO-UHFFFAOYAE |
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| 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 |
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| StdInChIKey = YNWOMOUVWNKICO-UHFFFAOYSA-N |
| StdInChIKey = YNWOMOUVWNKICO-UHFFFAOYSA-N |
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'''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>{{ |
'''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> |
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==See also== |
== See also == |
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* [[CID-16020046]] |
* [[CID-16020046]] |
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* [[PSB-SB-1202]] |
* [[PSB-SB-1202]] |
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== References == |
== References == |
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{{reflist}} |
{{reflist}} |
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{{Cannabinoids}} |
{{Cannabinoids}} |
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[[Category:Cannabinoids]] |
[[Category:Cannabinoids]] |
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[[Category:Coumarins]] |
Latest revision as of 04:24, 25 March 2024
Identifiers | |
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PubChem CID | |
ChemSpider | |
CompTox Dashboard (EPA) | |
Chemical and physical data | |
Formula | C26H32O4 |
Molar mass | 408.538 g·mol−1 |
3D model (JSmol) | |
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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]
- ^ 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.
- ^ 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.