(E)-N-((S)-1-Benzo[1,3]dioxol-5-yl-ethyl)-3-(2-chloro-phenyl)-acrylamide

ID: ALA180886

Chembl Id: CHEMBL180886

PubChem CID: 35079367

Max Phase: Preclinical

Molecular Formula: C18H16ClNO3

Molecular Weight: 329.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](NC(=O)/C=C/c1ccccc1Cl)c1ccc2c(c1)OCO2

Standard InChI:  InChI=1S/C18H16ClNO3/c1-12(14-6-8-16-17(10-14)23-11-22-16)20-18(21)9-7-13-4-2-3-5-15(13)19/h2-10,12H,11H2,1H3,(H,20,21)/b9-7+/t12-/m0/s1

Standard InChI Key:  FVULDXTVYUQILH-CRALRDPISA-N

Alternative Forms

1. Parent:

   

   ALA180886

   (E)-N-[(1S)-1-(1,3-benzodioxol-5-yl)ethyl]-3-(2-chlorophenyl)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: 329.78

Molecular Weight (Monoisotopic): 329.0819

AlogP: 3.96

#Rotatable Bonds: 4

Polar Surface Area: 47.56

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.92

CX LogD: 3.92

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.86

Np Likeness Score: -0.89

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, Sun LQ, He H, Chen J, Starrett JE, Dextraze P, Daris JP, Boissard CG, Pieschl RL, Gribkoff VK, Natale J, Knox RJ, Harden DG, Thompson MW, Fitzpatrick W, Weaver D, Wu D, Gao Q, Dworetzky SI..  (2004)  Synthesis and KCNQ2 opener activity of N-(1-benzo[1,3]dioxol-5-yl-ethyl, N-[1-(2,3-dihydro-benzofuran-5-yl)-ethyl, and N-[1-(2,3-dihydro-1H-indol-5-yl)-ethyl acrylamides.,  14  (17): [PMID:15357987] [10.1016/j.bmcl.2004.06.035]

3. Wu YJ, Sun LQ, He H, Chen J, Starrett JE, Dextraze P, Daris JP, Boissard CG, Pieschl RL, Gribkoff VK, Natale J, Knox RJ, Harden DG, Thompson MW, Fitzpatrick W, Weaver D, Wu D, Gao Q, Dworetzky SI..  (2004)  Synthesis and KCNQ2 opener activity of N-(1-benzo[1,3]dioxol-5-yl-ethyl, N-[1-(2,3-dihydro-benzofuran-5-yl)-ethyl, and N-[1-(2,3-dihydro-1H-indol-5-yl)-ethyl acrylamides.,  14  (17): [PMID:15357987] [10.1016/j.bmcl.2004.06.035]

4. 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