ML337

ML337
Identifiers
	IUPAC name (R)-(2-fluoro-4-[(4-methoxyphenyl)ethynyl]phenyl)(3-hydroxypiperidin-1-yl)methanone;
CAS Number	1443118-44-2;
PubChem CID	60204017;
IUPHAR/BPS	8765;
ChemSpider	29785018;
ChEMBL	ChEMBL2385886;
Chemical and physical data
Formula	C21H20FNO3
Molar mass	353.393 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=CC=C(C=C1)C#CC2=CC(=C(C=C2)C(=O)N3CCC[C@H](C3)O)F;
	InChI InChI=1S/C21H20FNO3/c1-26-18-9-6-15(7-10-18)4-5-16-8-11-19(20(22)13-16)21(25)23-12-2-3-17(24)14-23/h6-11,13,17,24H,2-3,12,14H2,1H3/t17-/m1/s1; Key:QBCRLDPMQHPGIM-QGZVFWFLSA-N;

ML337 is an experimental drug that acts as a negative allosteric modulator selective for the glutamate receptor mGluR3. It has only moderate potency with an IC₅₀ of 450 nM, but is highly selective over the closely related subtype mGluR2 with no effect even at 30,000 nM, and so has been used to study the effects of mGluR3 in isolation, which had previously been difficult to separate from mGluR2 mediated effects.^[1]^[2]^[3]

References

^ Wenthur C, Daniels JS, Morrison R, Engers JL, Niswender CM, Conn PJ, et al. (December 2012). "Development of a Second Generation mGlu3 NAM Probe". Probe Reports from the NIH Molecular Libraries Program [Internet]. Bethesda (MD): National Center for Biotechnology Information (US). PMID 23885366.
^ Wenthur CJ, Morrison R, Felts AS, Smith KA, Engers JL, Byers FW, et al. (June 2013). "Discovery of (R)-(2-fluoro-4-((-4-methoxyphenyl)ethynyl)phenyl) (3-hydroxypiperidin-1-yl)methanone (ML337), an mGlu3 selective and CNS penetrant negative allosteric modulator (NAM)". Journal of Medicinal Chemistry. 56 (12): 5208–5212. doi:10.1021/jm400439t. PMC 3769689. PMID 23718281.
^ Olivero G, Bonfiglio T, Vergassola M, Usai C, Riozzi B, Battaglia G, et al. (December 2017). "Immuno-pharmacological characterization of group II metabotropic glutamate receptors controlling glutamate exocytosis in mouse cortex and spinal cord". British Journal of Pharmacology. 174 (24): 4785–4796. doi:10.1111/bph.14061. PMC 5727332. PMID 28967122.

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[1] Wenthur C, Daniels JS, Morrison R, Engers JL, Niswender CM, Conn PJ, et al. (December 2012). "Development of a Second Generation mGlu3 NAM Probe". Probe Reports from the NIH Molecular Libraries Program [Internet]. Bethesda (MD): National Center for Biotechnology Information (US). PMID 23885366.

[2] Wenthur CJ, Morrison R, Felts AS, Smith KA, Engers JL, Byers FW, et al. (June 2013). "Discovery of (R)-(2-fluoro-4-((-4-methoxyphenyl)ethynyl)phenyl) (3-hydroxypiperidin-1-yl)methanone (ML337), an mGlu3 selective and CNS penetrant negative allosteric modulator (NAM)". Journal of Medicinal Chemistry. 56 (12): 5208–5212. doi:10.1021/jm400439t. PMC 3769689. PMID 23718281.

[3] Olivero G, Bonfiglio T, Vergassola M, Usai C, Riozzi B, Battaglia G, et al. (December 2017). "Immuno-pharmacological characterization of group II metabotropic glutamate receptors controlling glutamate exocytosis in mouse cortex and spinal cord". British Journal of Pharmacology. 174 (24): 4785–4796. doi:10.1111/bph.14061. PMC 5727332. PMID 28967122.

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