(E)-3-(2-Fluoro-phenyl)-N-{(S)-1-[3-(6-fluoro-pyridin-3-yl)-phenyl]-ethyl}-acrylamide

ID: ALA361184

Chembl Id: CHEMBL361184

PubChem CID: 10270128

Max Phase: Preclinical

Molecular Formula: C22H18F2N2O

Molecular Weight: 364.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](NC(=O)/C=C/c1ccccc1F)c1cccc(-c2ccc(F)nc2)c1

Standard InChI:  InChI=1S/C22H18F2N2O/c1-15(26-22(27)12-10-16-5-2-3-8-20(16)23)17-6-4-7-18(13-17)19-9-11-21(24)25-14-19/h2-15H,1H3,(H,26,27)/b12-10+/t15-/m0/s1

Standard InChI Key:  UZXOICNXSPXWIT-PABFRNLHSA-N

Alternative Forms

1. Parent:

   

   ALA361184

   (E)-3-(2-fluorophenyl)-N-[(1S)-1-[3-(6-fluoropyridin-3-yl)phenyl]ethyl]prop-2-enamide

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: 364.39

Molecular Weight (Monoisotopic): 364.1387

AlogP: 4.92

#Rotatable Bonds: 5

Polar Surface Area: 41.99

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.80

CX LogD: 4.80

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.52

Np Likeness Score: -1.20

References

1. L'Heureux A, Martel A, He H, Chen J, Sun LQ, Starrett JE, Natale J, Dworetzky SI, Knox RJ, Harden DG, Weaver D, Thompson MW, Wu YJ..  (2005)  (S,E)-N-[1-(3-heteroarylphenyl)ethyl]-3-(2-fluorophenyl)acrylamides: synthesis and KCNQ2 potassium channel opener activity.,  15  (2): [PMID:15603955] [10.1016/j.bmcl.2004.10.065]

2. Wu YJ, Conway CM, Sun LQ, Machet F, Chen J, Chen P, He H, Bourin C, Calandra V, Polino JL, Davis CD, Heman K, Gribkoff VK, Boissard CG, Knox RJ, Thompson MW, Fitzpatrick W, Weaver D, Harden DG, Natale J, Dworetzky SI, Starrett JE..  (2013)  Discovery of (S,E)-3-(2-fluorophenyl)-N-(1-(3-(pyridin-3-yloxy)phenyl)ethyl)-acrylamide as a potent and efficacious KCNQ2 (Kv7.2) opener for the treatment of neuropathic pain.,  23  (22): [PMID:24070783] [10.1016/j.bmcl.2013.08.092]

Source

Source(1):

• Scientific Literature