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(CAS: 2148924-04-1 )

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Background Information of VU6009543

VU6009543 is an muscarinic acetylcholine receptor subtype 4 (M4) positive allosteric modulator (PAM) with an EC50 of 1130 nM for rM4. M4 PAMs have garnered a great deal of attention as a new therapeutic approach for the treatment of schizophrenia (both the positive and cognitive symptom clusters), Huntington’s disease and Parkinson’s disease.

Solubility of VU6009543

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Mechanism and Indications

Signaling Pathways Neuronal Signaling GPCR/G Protein
Target mAChR
Research Area Neurological Disease

Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase

Chemical Information

M.Wt Formula CAS No. Synonyms
398.41 C21H20F2N4O2 2148924-04-1

Structure Information of VU6009543

Smiles C1C(C)=C2C=C(C(NC3CN(C4C=CN=C(OC(F)F)C=4)C3)=O)C=CC2=NC=1C
InChI InChI=1S/C21H20F2N4O2/c1-12-7-13(2)25-18-4-3-14(8-17(12)18)20(28)26-15-10-27(11-15)16-5-6-24-19(9-16)29-21(22)23/h3-9,15,21H,10-11H2,1-2H3,(H,26,28)

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Chemical and Physical Properties

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[1].Long MF, et al. Discovery of a novel 2,4-dimethylquinoline-6-carboxamide M4 positive allosteric modulator (PAM) chemotype via scaffold hopping. Bioorg Med Chem Lett. 2017 Nov 15;27(22):4999-5001.
This Letter details our efforts to replace the 3-amino moiety, an essential pharmacophore for M4 PAM activity in most M4 PAMs to date, within the thieno[2,3-b]pyridine core, as the β-amino carboxamide motif has been shown to engender poor solubility, varying degrees of P-gp efflux and represents a structural alert. A scaffold hopping exercise identified a novel 2,4-dimethylquinoline carboxamide core that provided M4 PAM activity and good CNS penetration without an amino moiety. In addition, MacMillan photoredox catalysis chemistry was essential for construction of the 2,4-dimethylquinoline core.

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