From Wikipedia, the free encyclopedia
Chemical compound
ADX-47273
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(S)-(4-fluorophenyl)-(3-[3-(4-fluoro-phenyl)-[1,2,4]-oxadiazol-5-yl]piperidin-1-yl)methanone
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CAS Number | -
851881-60-2 Y
851881-59-9 (R isomer), 837413-22-6 (racemate)
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CompTox Dashboard (
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Formula | C20H17F2N3O2 |
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Molar mass | 369.372 g·mol−1 |
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3D model (
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FC1=CC=C(C(N2CCC[C@@H](C2)C3=NC(C4=CC=C(F)C=C4)=NO3)=O)C=C1
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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 YKey:VXQCCZHCFBHTTD-HNNXBMFYSA-N Y
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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]
See also
References
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^ 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.
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^ Stauffer SR (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.
PMID
22860171.
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^ 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.
S2CID
19362501.
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^ 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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Group I |
mGluR1Tooltip Metabotropic glutamate receptor 1 | |
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mGluR5Tooltip Metabotropic glutamate receptor 5 | |
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Group II |
mGluR2Tooltip Metabotropic glutamate receptor 2 | |
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mGluR3Tooltip Metabotropic glutamate receptor 3 | |
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Group III |
mGluR4Tooltip Metabotropic glutamate receptor 4 | |
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mGluR6Tooltip Metabotropic glutamate receptor 6 | |
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mGluR7Tooltip Metabotropic glutamate receptor 7 | |
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mGluR8Tooltip Metabotropic glutamate receptor 8 | |
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