N-(6,7-dichloro-2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-5-yl)-N-(3,3,3-trifluoropropyl)ethanesulfonamide

ID: ALA399519

PubChem CID: 23661726

Max Phase: Preclinical

Molecular Formula: C13H12Cl2F3N3O4S

Molecular Weight: 434.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCS(=O)(=O)N(CCC(F)(F)F)c1c(Cl)c(Cl)cc2[nH]c(=O)c(=O)[nH]c12

Standard InChI:  InChI=1S/C13H12Cl2F3N3O4S/c1-2-26(24,25)21(4-3-13(16,17)18)10-8(15)6(14)5-7-9(10)20-12(23)11(22)19-7/h5H,2-4H2,1H3,(H,19,22)(H,20,23)

Standard InChI Key:  MVGABTCTHPSFLI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   -3.2236   -7.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2249   -8.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5119   -8.9725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5139   -7.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7957   -7.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7967   -8.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0792   -8.9769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3562   -8.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3553   -7.7295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0773   -7.3096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3600   -7.3186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573   -8.9774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5178   -6.4942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8053   -6.0783    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0954   -5.6603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3881   -6.7901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2214   -5.3661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2342   -6.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2380   -5.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9399   -8.9711    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.9384   -7.3201    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.9543   -4.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6703   -4.4366    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3655   -5.5662    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5413   -4.1367    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1025   -4.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  4 13  1  0
  3  6  2  0
 13 14  1  0
  1  2  2  0
 14 15  1  0
  5  4  2  0
 14 16  2  0
  4  1  1  0
 14 17  2  0
  5 10  1  0
 13 18  1  0
  6  7  1  0
 18 19  1  0
  7  8  1  0
  2 20  1  0
  8  9  1  0
  1 21  1  0
  9 10  1  0
 19 22  1  0
  5  6  1  0
 22 23  1  0
  9 11  2  0
 22 24  1  0
 22 25  1  0
  8 12  2  0
 15 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA399519

   N-(6,7-dichloro-2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-5-yl)-N-(3,3,3-trifluoropropyl)ethanesulfonamide

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: 434.22

Molecular Weight (Monoisotopic): 432.9878

AlogP: 2.63

#Rotatable Bonds: 5

Polar Surface Area: 103.10

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.11

CX Basic pKa: ┄

CX LogP: 2.74

CX LogD: 2.74

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.71

Np Likeness Score: -1.24

References

1. Deur C, Agrawal AK, Baum H, Booth J, Bove S, Brieland J, Bunker A, Connolly C, Cornicelli J, Dumin J, Finzel B, Gan X, Guppy S, Kamilar G, Kilgore K, Lee P, Loi CM, Lou Z, Morris M, Philippe L, Przybranowski S, Riley F, Samas B, Sanchez B, Tecle H, Wang Z, Welch K, Wilson M, Yates K..  (2007)  N-(6,7-dichloro-2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-5-yl)-N-alkylsulfonamides as peripherally restricted N-methyl-D-aspartate receptor antagonists for the treatment of pain.,  17  (16): [PMID:17562362] [10.1016/j.bmcl.2007.05.083]

2. Deur C, Agrawal AK, Baum H, Booth J, Bove S, Brieland J, Bunker A, Connolly C, Cornicelli J, Dumin J, Finzel B, Gan X, Guppy S, Kamilar G, Kilgore K, Lee P, Loi CM, Lou Z, Morris M, Philippe L, Przybranowski S, Riley F, Samas B, Sanchez B, Tecle H, Wang Z, Welch K, Wilson M, Yates K..  (2007)  N-(6,7-dichloro-2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-5-yl)-N-alkylsulfonamides as peripherally restricted N-methyl-D-aspartate receptor antagonists for the treatment of pain.,  17  (16): [PMID:17562362] [10.1016/j.bmcl.2007.05.083]

3. Deur C, Agrawal AK, Baum H, Booth J, Bove S, Brieland J, Bunker A, Connolly C, Cornicelli J, Dumin J, Finzel B, Gan X, Guppy S, Kamilar G, Kilgore K, Lee P, Loi CM, Lou Z, Morris M, Philippe L, Przybranowski S, Riley F, Samas B, Sanchez B, Tecle H, Wang Z, Welch K, Wilson M, Yates K..  (2007)  N-(6,7-dichloro-2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-5-yl)-N-alkylsulfonamides as peripherally restricted N-methyl-D-aspartate receptor antagonists for the treatment of pain.,  17  (16): [PMID:17562362] [10.1016/j.bmcl.2007.05.083]

Source

Source(1):

• Scientific Literature