N-(3-chloro-4-(4-fluoro-1,3-dioxoisoindolin-2-yl)phenyl)-3-methylfuran-2-carboxamide

ID: ALA3628113

Chembl Id: CHEMBL3628113

PubChem CID: 122193177

Max Phase: Preclinical

Molecular Formula: C20H12ClFN2O4

Molecular Weight: 398.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccoc1C(=O)Nc1ccc(N2C(=O)c3cccc(F)c3C2=O)c(Cl)c1

Standard InChI:  InChI=1S/C20H12ClFN2O4/c1-10-7-8-28-17(10)18(25)23-11-5-6-15(13(21)9-11)24-19(26)12-3-2-4-14(22)16(12)20(24)27/h2-9H,1H3,(H,23,25)

Standard InChI Key:  HHRZBUWNLICHOO-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA3628113

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Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 398.78

Molecular Weight (Monoisotopic): 398.0470

AlogP: 4.43

#Rotatable Bonds: 3

Polar Surface Area: 79.62

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.90

CX Basic pKa: ┄

CX LogP: 3.99

CX LogD: 3.99

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.66

Np Likeness Score: -1.72

References

1. Garcia-Barrantes PM, Cho HP, Niswender CM, Byers FW, Locuson CW, Blobaum AL, Xiang Z, Rook JM, Conn PJ, Lindsley CW..  (2015)  Development of Novel, CNS Penetrant Positive Allosteric Modulators for the Metabotropic Glutamate Receptor Subtype 1 (mGlu1), Based on an N-(3-Chloro-4-(1,3-dioxoisoindolin-2-yl)phenyl)-3-methylfuran-2-carboxamide Scaffold, That Potentiate Wild Type and Mutant mGlu1 Receptors Found in Schizophrenics.,  58  (20): [PMID:26426481] [10.1021/acs.jmedchem.5b00727]

2. Garcia-Barrantes PM, Cho HP, Blobaum AL, Niswender CM, Conn PJ, Lindsley CW..  (2016)  Lead optimization of the VU0486321 series of mGlu1 PAMs. Part 3. Engineering plasma stability by discovery and optimization of isoindolinone analogs.,  26  (8): [PMID:26988302] [10.1016/j.bmcl.2016.03.031]

Source

Source(1):

• Scientific Literature