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'''ADX-47273''' is a research pharmaceutical developed by ] which acts as a ] (PAM) selective for the ] subtype ].<ref name="pmid16722652">{{cite journal |vauthors =de Paulis T, Hemstapat K, Chen Y, Zhang Y, Saleh S, Alagille D, Baldwin RM, Tamagnan GD, Conn PJ |title=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=Journal of Medicinal Chemistry |volume=49 |issue=11 |pages=3332–44 |date=June 2006 |pmid=16722652 |doi=10.1021/jm051252j }}</ref><ref>{{cite journal|last1=Stauffer|first1=Shaun R.|title=Progress toward Positive Allosteric Modulators of the Metabotropic Glutamate Receptor Subtype 5 (mGlu5)|journal=ACS Chemical Neuroscience|date=17 August 2011|volume=2|issue=8|pages=450–470|doi=10.1021/cn2000519|pmc=3369763|pmid=22860171}}</ref> It has ] and ] effects in animal studies,<ref name="pmid18753411">{{cite journal |vauthors =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 |title=ADX47273 -oxadiazol-5-yl]-piperidin-1-yl}-methanone]: a novel metabotropic glutamate receptor 5-selective positive allosteric modulator with preclinical antipsychotic-like and procognitive activities |journal=The Journal of Pharmacology and Experimental Therapeutics |volume=327 |issue=3 |pages=827–39 |date=December 2008|pmid=18753411 |doi=10.1124/jpet.108.136580 }}</ref> and has been used as a ] to develop improved derivatives.<ref name="pmid19197923">{{cite journal |vauthors =Engers DW, Rodriguez AL, Williams R, Hammond AS, Venable D, Oluwatola O, Sulikowski GA, Conn PJ, Lindsley CW |title=Synthesis, SAR and unanticipated pharmacological profiles of analogues of the mGluR5 ago-potentiator ADX-47273 |journal=ChemMedChem |volume=4 |issue=4 |pages=505–11 |date=April 2009 |pmid=19197923 |doi=10.1002/cmdc.200800357 |pmc=2865690}}</ref> '''ADX-47273''' is a research pharmaceutical developed by ] which acts as a ] (PAM) selective for the ] subtype ].<ref name="pmid16722652">{{cite journal |vauthors =de Paulis T, Hemstapat K, Chen Y, Zhang Y, Saleh S, Alagille D, Baldwin RM, Tamagnan GD, Conn PJ |title=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=Journal of Medicinal Chemistry |volume=49 |issue=11 |pages=3332–44 |date=June 2006 |pmid=16722652 |doi=10.1021/jm051252j }}</ref><ref>{{cite journal|last1=Stauffer|first1=Shaun R.|title=Progress toward Positive Allosteric Modulators of the Metabotropic Glutamate Receptor Subtype 5 (mGlu5)|journal=ACS Chemical Neuroscience|date=17 August 2011|volume=2|issue=8|pages=450–470|doi=10.1021/cn2000519|pmc=3369763|pmid=22860171}}</ref> It has ] and ] effects in animal studies,<ref name="pmid18753411">{{cite journal |vauthors =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 |title=ADX47273 -oxadiazol-5-yl]-piperidin-1-yl}-methanone]: a novel metabotropic glutamate receptor 5-selective positive allosteric modulator with preclinical antipsychotic-like and procognitive activities |journal=The Journal of Pharmacology and Experimental Therapeutics |volume=327 |issue=3 |pages=827–39 |date=December 2008|pmid=18753411 |doi=10.1124/jpet.108.136580 }}</ref> and has been used as a ] to develop improved derivatives.<ref name="pmid19197923">{{cite journal |vauthors =Engers DW, Rodriguez AL, Williams R, Hammond AS, Venable D, Oluwatola O, Sulikowski GA, Conn PJ, Lindsley CW |title=Synthesis, SAR and unanticipated pharmacological profiles of analogues of the mGluR5 ago-potentiator ADX-47273 |journal=ChemMedChem |volume=4 |issue=4 |pages=505–11 |date=April 2009 |pmid=19197923 |doi=10.1002/cmdc.200800357 |pmc=2865690}}</ref>
==Synthesis==
]


Ex 4: The heterocycle formation between 1-Boc-piperidine-3-carboxylic acid ('''1''') and 4-Fluorobenzamidoxime ('''2''') gave ('''3'''). Deprotection with acid gave 3-piperidine ('''4'''). Functionalization with the para-fluoro-benzoyl chloride completed the synthesis of ADX-47273 ('''4''').
==See also== ==See also==
* ] * ]

Revision as of 10:19, 20 November 2022

Pharmaceutical compound
ADX-47273
Identifiers
IUPAC name
  • (S)-(4-fluorophenyl)-(3--oxadiazol-5-yl]piperidin-1-yl)methanone
CAS Number
  • 851881-60-2
    851881-59-9 (R isomer),
    837413-22-6 (racemate)
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H17F2N3O2
Molar mass369.372 g·mol
3D model (JSmol)
SMILES
  • FC1=CC=C(C(N2CCC(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. It has nootropic and antipsychotic effects in animal studies, and has been used as a lead compound to develop improved derivatives.

See also

References

  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, 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. 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 -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.
  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.
Metabotropic glutamate receptor modulators
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
See also: Receptor/signaling modulators • Ionotropic glutamate receptor modulators • Glutamate metabolism/transport modulators


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