KSC-12-192: Difference between revisions

KSC-12-192
Clinical data
Other names	"probe 1.1"
ATC code	None;
Identifiers
	IUPAC name 2-[4-(furan-2-ylmethyl)-5-[[4-methyl-3-(trifluoromethyl)phenyl]methylsulfanyl]-1,2,4-triazol-3-yl]pyridine;
PubChem CID	46245518;
ChemSpider	58145205;
ChEMBL	ChEMBL4458783;
Chemical and physical data
Formula	C21H17F3N4OS
Molar mass	430.45 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=C(C=C(C=C1)CSC2=NN=C(N2CC3=CC=CO3)C4=CC=CC=N4)C(F)(F)F;
	InChI InChI=1S/C21H17F3N4OS/c1-14-7-8-15(11-17(14)21(22,23)24)13-30-20-27-26-19(18-6-2-3-9-25-18)28(20)12-16-5-4-10-29-16/h2-11H,12-13H2,1H3; Key:OQJGZGAYSCWFCK-UHFFFAOYSA-N;

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Revision as of 09:55, 21 March 2023

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KSC-12-192 is a drug that is used in scientific research to study the κ-opioid receptor, where it acts as a biased agonist.^[1]

KSC-12-192 preferentially activates G-protein coupling over β-arrestin 2 recruitment in vitro, an intrinsic activity shared with many other KOR ligands developed to separate KOR-mediated analgesia from accompanying dysphoria.

Compared with most of the known KOR G-protein biased agonists, KSC-12-192 and its parent compound ML138 have no stereoisomers.

Name(s)			X	R₁	R₂	R₃
	KSC-12-192	probe 1.1	O	H	CH₃	CF₃
ML138	KSC-5-240	probe 1	O	H	Cl	Cl
KUC103903N	KSC-5-247G		S	H	Cl	Cl
KUC105892N	KSC-12-193	probe 1.3	S	H	CH₃	CF₃
KUC105904N	KSC-12-238-B5	probe 1.4	O	CH₃	CH₃	CF₃
KUC105903N	KSC-12-238-B4		O	CH₃	Cl	Cl

References

^ Zhou, Lei; Lovell, Kimberly M.; Frankowski, Kevin J.; Slauson, Stephen R.; Phillips, Angela M.; Streicher, John M.; Stahl, Edward; Schmid, Cullen L.; Hodder, Peter; Madoux, Franck; Cameron, Michael D.; Prisinzano, Thomas E.; Aubé, Jeffrey; Bohn, Laura M. (2013-12-20). "Development of functionally selective, small molecule agonists at kappa opioid receptors". The Journal of Biological Chemistry. 288 (51): 36703–36716. doi:10.1074/jbc.M113.504381. ISSN 1083-351X. PMC 3868780. PMID 24187130.{{cite journal}}: CS1 maint: unflagged free DOI (link)

[1] Zhou, Lei; Lovell, Kimberly M.; Frankowski, Kevin J.; Slauson, Stephen R.; Phillips, Angela M.; Streicher, John M.; Stahl, Edward; Schmid, Cullen L.; Hodder, Peter; Madoux, Franck; Cameron, Michael D.; Prisinzano, Thomas E.; Aubé, Jeffrey; Bohn, Laura M. (2013-12-20). "Development of functionally selective, small molecule agonists at kappa opioid receptors". The Journal of Biological Chemistry. 288 (51): 36703–36716. doi:10.1074/jbc.M113.504381. ISSN 1083-351X. PMC 3868780. PMID 24187130.{{cite journal}}: CS1 maint: unflagged free DOI (link)

[1]

@@ Line 29: / Line 29: @@
 Compared with most of the known KOR G-protein biased agonists, KSC-12-192 and its parent compound [[ML138]] have no [[Stereoisomerism|stereoisomers]].
+<small>
 {| class="wikitable" style="background-color:white;text-align:center;"
 |-
-| || ||
+| || colspan="3" | Name(s)
 | style="width: 3em;" | X
 | style="width: 3em;" | R<sub>1</sub>
@@ Line 37: / Line 38: @@
 | style="width: 3em;" | R<sub>3</sub>
 |-
-| rowspan="6" | [[File:KSC-12-192 common scaffold.png|frameless]] || '''KSC-12-192''' || probe 1.1
+| rowspan="6" | [[File:KSC-12-192 common scaffold.png|frameless]] || || '''KSC-12-192'''|| probe 1.1
 | O || H || CH<sub>3</sub> || CF<sub>3</sub>
 |-
-| '''ML138''' (KSC-5-240) || probe 1
+| '''ML138''' || KSC-5-240 || probe 1
 | O || H || Cl || Cl
 |-
-| KUC103903N  (KSC-5-247G) ||
+| KUC103903N || KSC-5-247G ||
 | S || H || Cl || Cl
 |-
-| KUC105892N (KSC-12-193) || probe 1.3
+| KUC105892N || KSC-12-193 || probe 1.3
 | S || H || CH<sub>3</sub> || CF<sub>3</sub>
 |-
-| KUC105904N (KSC-12-238-B5) || probe 1.4
+| KUC105904N || KSC-12-238-B5 || probe 1.4
 | O || CH<sub>3</sub> || CH<sub>3</sub> || CF<sub>3</sub>
 |-
-| KUC105903N (KSC-12-238-B4) ||
+| KUC105903N || KSC-12-238-B4 ||
 | O || CH<sub>3</sub> || Cl || Cl
 |}
+</small>
 == References ==