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VU-0238429

From Wikipedia, the free encyclopedia

VU-0238429
Identifiers
  • 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−1
3D model (JSmol)
  • 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=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 checkY
  • Key:CKLGZXFOLMHCMC-UHFFFAOYSA-N checkY
  (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,[1] and is structurally derived from older M1-selective positive allosteric modulators such as VU-0119498.[2][3] Replacing the O-methyl- by a phenyl group further improves the receptor subtype selectivity.[4]

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.
This page was last edited on 19 November 2023, at 02:16
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