2-(2-Chloro-phenyl)-9-(3-methoxy-benzyl)-2,3,7,8,9,10-hexahydro-6H-2,3,5a,9-tetraaza-cyclohepta[e]indene-1,5-dione hydrochloride

ID: ALA1927153

PubChem CID: 57401057

Max Phase: Preclinical

Molecular Formula: C24H24Cl2N4O3

Molecular Weight: 450.93

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(CN2CCCn3c(c4c(=O)n(-c5ccccc5Cl)[nH]c4cc3=O)C2)c1.Cl

Standard InChI:  InChI=1S/C24H23ClN4O3.ClH/c1-32-17-7-4-6-16(12-17)14-27-10-5-11-28-21(15-27)23-19(13-22(28)30)26-29(24(23)31)20-9-3-2-8-18(20)25;/h2-4,6-9,12-13,26H,5,10-11,14-15H2,1H3;1H

Standard InChI Key:  OLYAETSYYDQEHW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    2.6625  -23.7812    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.9750  -23.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3649  -23.8133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9260  -24.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0972  -24.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7093  -23.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1506  -23.0502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6573  -25.1860    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.8829  -23.7162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3732  -24.3682    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4258  -23.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6298  -23.2554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6002  -24.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8726  -24.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1699  -24.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7351  -22.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2263  -21.4610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5548  -21.4650    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5339  -22.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1982  -23.2059    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9318  -22.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0687  -22.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7126  -22.2552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5598  -24.4212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9499  -20.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5640  -20.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2167  -20.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6027  -19.4309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2074  -18.7561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5779  -18.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9603  -19.4427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9774  -18.0879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5918  -17.4038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  8  1  0
  4  5  2  0
  6  9  1  0
  9 10  1  0
  5  6  1  0
 10 13  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 19 20  1  0
 12 11  1  0
 11 23  2  0
 11  9  1  0
 15 24  2  0
 12 13  1  0
 18 25  1  0
  3  4  1  0
 25 26  1  0
  6  7  2  0
 26 27  2  0
  7  2  1  0
 27 28  1  0
  2  3  2  0
 28 29  2  0
 12 21  2  0
 29 30  1  0
 13 14  2  0
 30 31  2  0
 31 26  1  0
 14 15  1  0
 30 32  1  0
 15 20  1  0
 32 33  1  0
M  END

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: 450.93

Molecular Weight (Monoisotopic): 450.1459

AlogP: 3.55

#Rotatable Bonds: 4

Polar Surface Area: 72.26

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.44

CX Basic pKa: 7.32

CX LogP: 0.71

CX LogD: 0.90

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.52

Np Likeness Score: -1.26

References

1. Gaggini F, Laleu B, Orchard M, Fioraso-Cartier L, Cagnon L, Houngninou-Molango S, Gradia A, Duboux G, Merlot C, Heitz F, Szyndralewiez C, Page P..  (2011)  Design, synthesis and biological activity of original pyrazolo-pyrido-diazepine, -pyrazine and -oxazine dione derivatives as novel dual Nox4/Nox1 inhibitors.,  19  (23): [PMID:22041175] [10.1016/j.bmc.2011.10.016]

Source

Source(1):

• Scientific Literature