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VU-0238429

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Chemical compound Pharmaceutical compound
VU-0238429
Identifiers
IUPAC name
  • 1-(4-methoxybenzyl)-5-(trifluoromethoxy)indole-2,3-dione
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H12F3NO4
Molar mass351.281 g·mol
3D model (JSmol)
SMILES
  • c2cc(OC)ccc2CN(C(=O)C1=O)c3ccc(cc13)OC(F)(F)F

  • COc1ccc(cc1)CN2c3ccc(cc3C(=O)C2=O)OC(F)(F)F
InChI
  • InChI=1S/C17H12F3NO4/c1-24-11-4-2-10(3-5-11)9-21-14-7-6-12(25-17(18,19)20)8-13(14)15(22)16(21)23/h2-8H,9H2,1H3
  • Key:CKLGZXFOLMHCMC-UHFFFAOYSA-N
  (verify)

VU-0238429 is a drug which acts as a selective positive allosteric modulator for the muscarinic acetylcholine receptor M5. It was the first selective ligand developed for the M5 subtype, and is structurally derived from older M1-selective positive allosteric modulators such as VU-0119498. Replacing the O-methyl- by a phenyl group further improves the receptor subtype selectivity.

References

  1. Bridges TM, Marlo JE, Niswender CM, Jones CK, Jadhav SB, Gentry PR, et al. (June 2009). "Discovery of the first highly M5-preferring muscarinic acetylcholine receptor ligand, an M5 positive allosteric modulator derived from a series of 5-trifluoromethoxy N-benzyl isatins". Journal of Medicinal Chemistry. 52 (11): 3445–3448. doi:10.1021/jm900286j. PMC 3875304. PMID 19438238.
  2. Conn PJ, Jones CK, Lindsley CW (March 2009). "Subtype-selective allosteric modulators of muscarinic receptors for the treatment of CNS disorders". Trends in Pharmacological Sciences. 30 (3): 148–155. doi:10.1016/j.tips.2008.12.002. PMC 2907736. PMID 19201489.
  3. Bridges TM, Kennedy JP, Hopkins CR, Conn PJ, Lindsley CW (October 2010). "Heterobiaryl and heterobiaryl ether derived M5 positive allosteric modulators". Bioorganic & Medicinal Chemistry Letters. 20 (19): 5617–5622. doi:10.1016/j.bmcl.2010.08.042. PMC 3179183. PMID 20801651.
  4. Bridges TM, Phillip Kennedy J, Noetzel MJ, Breininger ML, Gentry PR, Conn PJ, Lindsley CW (March 2010). "Chemical lead optimization of a pan Gq mAChR M1, M3, M5 positive allosteric modulator (PAM) lead. Part II: development of a potent and highly selective M1 PAM". Bioorganic & Medicinal Chemistry Letters. 20 (6): 1972–1975. doi:10.1016/j.bmcl.2010.01.109. PMC 2834874. PMID 20156687.
Muscarinic acetylcholine receptor modulators
mAChRsTooltip Muscarinic acetylcholine receptors
Agonists
Antagonists
Precursors
(and prodrugs)
See also
Receptor/signaling modulators
Nicotinic acetylcholine receptor modulators
Acetylcholine metabolism/transport modulators
Categories:
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