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ADX-47273

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
ADX-47273
Identifiers
  • (S)-(4-fluorophenyl)-(3-[3-(4-fluoro-phenyl)-[1,2,4]-oxadiazol-5-yl]piperidin-1-yl)methanone
CAS Number
  • 851881-60-2 checkY
    851881-59-9 (R isomer),
    837413-22-6 (racemate)
PubChemCID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC20H17F2N3O2
Molar mass369.372 g·mol−1
3D model (JSmol)
  • FC1=CC=C(C(N2CCC[C@@H](C2)C3=NC(C4=CC=C(F)C=C4)=NO3)=O)C=C1
  • 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 checkY
  • Key:VXQCCZHCFBHTTD-HNNXBMFYSA-N checkY
  (verify)

ADX-47273 is a research pharmaceutical developed byAddex Therapeutics which acts as apositive allosteric modulator (PAM) selective for themetabotropic glutamate receptor subtypemGluR5.[1][2] It hasnootropic andantipsychotic effects in animal studies,[3] and has been used as alead compound to develop improved derivatives.[4]

See also

[edit]

References

[edit]
  1. ^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.
  2. ^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.
  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.S2CID 19362501.
  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.
Group I
mGluR1Tooltip Metabotropic glutamate receptor 1
mGluR5Tooltip Metabotropic glutamate receptor 5
Group II
mGluR2Tooltip Metabotropic glutamate receptor 2
mGluR3Tooltip Metabotropic glutamate receptor 3
Group III
mGluR4Tooltip Metabotropic glutamate receptor 4
mGluR6Tooltip Metabotropic glutamate receptor 6
mGluR7Tooltip Metabotropic glutamate receptor 7
mGluR8Tooltip Metabotropic glutamate receptor 8


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