ADX-47273

ADX-47273
Identifiers
	IUPAC name (S)-(4-fluorophenyl)-(3-[3-(4-fluoro-phenyl)-[1,2,4]-oxadiazol-5-yl]piperidin-1-yl)methanone;
CAS Number	851881-60-2 ; 851881-59-9 (R isomer),; 837413-22-6 (racemate);
PubChem CID	11383075;
IUPHAR/BPS	1420;
ChemSpider	9557988 ;
ChEMBL	ChEMBL381055 ;
CompTox Dashboard (EPA)	DTXSID80234386 ;
Chemical and physical data
Formula	C20H17F2N3O2
Molar mass	369.364 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES FC1=CC=C(C(N2CCC[C@@H](C2)C3=NC(C4=CC=C(F)C=C4)=NO3)=O)C=C1;
	InChI InChI=1S/C20H17F2N3O2/c21-16-7-3-13(4-8-16)18-23-19(27-24-18)15-2-1-11-25(12-15)20(26)14-5-9-17(22)10-6-14/h3-10,15H,1-2,11-12H2/t15-/m0/s1 ; Key:VXQCCZHCFBHTTD-HNNXBMFYSA-N ;
	(verify)

ADX-47273 is a research pharmaceutical developed by Addex Therapeutics which acts as a positive allosteric modulator (PAM) selective for the metabotropic glutamate receptor subtype mGluR₅.^[1]^[2] It has nootropic and antipsychotic effects in animal studies,^[3] and has been used as a lead compound to develop improved derivatives.^[4]

References

^ de Paulis T, Hemstapat K, Chen Y, Zhang Y, Saleh S, Alagille D, Baldwin RM, Tamagnan GD, Conn PJ (June 2006). "Substituent effects of N-(1,3-diphenyl-1H-pyrazol-5-yl)benzamides on positive allosteric modulation of the metabotropic glutamate-5 receptor in rat cortical astrocytes". Journal of Medicinal Chemistry. 49 (11): 3332–44. doi:10.1021/jm051252j. PMID 16722652.
^ Stauffer, Shaun R. (17 August 2011). "Progress toward Positive Allosteric Modulators of the Metabotropic Glutamate Receptor Subtype 5 (mGlu5)". ACS Chemical Neuroscience. 2 (8): 450–470. doi:10.1021/cn2000519. PMC 3369763.
^ Liu F, Grauer S, Kelley C, Navarra R, Graf R, Zhang G, Atkinson PJ, Popiolek M, Wantuch C, Khawaja X, Smith D, Olsen M, Kouranova E, Lai M, Pruthi F, Pulicicchio C, Day M, Gilbert A, Pausch MH, Brandon NJ, Beyer CE, Comery TA, Logue S, Rosenzweig-Lipson S, Marquis KL (December 2008). "ADX47273 [S-(4-fluoro-phenyl)-{3-[3-(4-fluoro-phenyl)-[1,2,4]-oxadiazol-5-yl]-piperidin-1-yl}-methanone]: a novel metabotropic glutamate receptor 5-selective positive allosteric modulator with preclinical antipsychotic-like and procognitive activities". The Journal of Pharmacology and Experimental Therapeutics. 327 (3): 827–39. doi:10.1124/jpet.108.136580. PMID 18753411.
^ Engers DW, Rodriguez AL, Williams R, Hammond AS, Venable D, Oluwatola O, Sulikowski GA, Conn PJ, Lindsley CW (April 2009). "Synthesis, SAR and unanticipated pharmacological profiles of analogues of the mGluR5 ago-potentiator ADX-47273". Chemmedchem. 4 (4): 505–11. doi:10.1002/cmdc.200800357. PMC 2865690. PMID 19197923.

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[pmid16722652-1] Paulis T, Hemstapat K, Chen Y, Zhang Y, Saleh S, Alagille D, Baldwin RM, Tamagnan GD, Conn PJ (June 2006). "Substituent effects of N-(1,3-diphenyl-1H-pyrazol-5-yl)benzamides on positive allosteric modulation of the metabotropic glutamate-5 receptor in rat cortical astrocytes". Journal of Medicinal Chemistry. 49 (11): 3332–44. doi:10.1021/jm051252j. PMID 16722652.

[2] Stauffer, Shaun R. (17 August 2011). "Progress toward Positive Allosteric Modulators of the Metabotropic Glutamate Receptor Subtype 5 (mGlu5)". ACS Chemical Neuroscience. 2 (8): 450–470. doi:10.1021/cn2000519. PMC 3369763.

[pmid18753411-3] Liu F, Grauer S, Kelley C, Navarra R, Graf R, Zhang G, Atkinson PJ, Popiolek M, Wantuch C, Khawaja X, Smith D, Olsen M, Kouranova E, Lai M, Pruthi F, Pulicicchio C, Day M, Gilbert A, Pausch MH, Brandon NJ, Beyer CE, Comery TA, Logue S, Rosenzweig-Lipson S, Marquis KL (December 2008). "ADX47273 [S-(4-fluoro-phenyl)-{3-[3-(4-fluoro-phenyl)-[1,2,4]-oxadiazol-5-yl]-piperidin-1-yl}-methanone]: a novel metabotropic glutamate receptor 5-selective positive allosteric modulator with preclinical antipsychotic-like and procognitive activities". The Journal of Pharmacology and Experimental Therapeutics. 327 (3): 827–39. doi:10.1124/jpet.108.136580. PMID 18753411.

[pmid19197923-4] Engers DW, Rodriguez AL, Williams R, Hammond AS, Venable D, Oluwatola O, Sulikowski GA, Conn PJ, Lindsley CW (April 2009). "Synthesis, SAR and unanticipated pharmacological profiles of analogues of the mGluR5 ago-potentiator ADX-47273". Chemmedchem. 4 (4): 505–11. doi:10.1002/cmdc.200800357. PMC 2865690. PMID 19197923.

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[2]

[3]

[4]

See also

References