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

ID: ALA399275

PubChem CID: 44443069

Max Phase: Preclinical

Molecular Formula: C13H15Cl2N3O5S

Molecular Weight: 396.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCCN(c1c(Cl)c(Cl)cc2[nH]c(=O)c(=O)[nH]c12)S(C)(=O)=O

Standard InChI:  InChI=1S/C13H15Cl2N3O5S/c1-23-5-3-4-18(24(2,21)22)11-9(15)7(14)6-8-10(11)17-13(20)12(19)16-8/h6H,3-5H2,1-2H3,(H,16,19)(H,17,20)

Standard InChI Key:  HCVVJCJMDGFGMO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    9.3529  -21.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3517  -22.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0646  -22.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0626  -21.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7808  -21.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7799  -22.2564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4974  -22.6717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2203  -22.2580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2213  -21.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4992  -21.0045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9366  -21.0134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9338  -22.6723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0587  -20.1891    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7713  -19.7732    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.4811  -19.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1885  -20.4850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3551  -19.0609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3424  -19.7799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3385  -18.9549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6366  -22.6659    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.6381  -21.0149    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.6221  -18.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6183  -17.7208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9019  -17.3116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8 12  2  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
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA399275

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

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: 396.25

Molecular Weight (Monoisotopic): 395.0109

AlogP: 1.33

#Rotatable Bonds: 6

Polar Surface Area: 112.33

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.11

CX Basic pKa: ┄

CX LogP: 1.10

CX LogD: 1.10

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.57

Np Likeness Score: -1.07

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