diethyl 4-(3-bromo-4-methylphenylamino)quinoline-3,6-dicarboxylate

ID: ALA209149

PubChem CID: 1566831

Max Phase: Preclinical

Molecular Formula: C22H21BrN2O4

Molecular Weight: 457.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1ccc2ncc(C(=O)OCC)c(Nc3ccc(C)c(Br)c3)c2c1

Standard InChI:  InChI=1S/C22H21BrN2O4/c1-4-28-21(26)14-7-9-19-16(10-14)20(17(12-24-19)22(27)29-5-2)25-15-8-6-13(3)18(23)11-15/h6-12H,4-5H2,1-3H3,(H,24,25)

Standard InChI Key:  IFNSWWMCNCFUKV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -2.2853  -13.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2865  -14.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5846  -15.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5864  -13.4795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8841  -13.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8833  -14.7673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1768  -15.1956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5253  -14.7635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5204  -13.8989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1824  -13.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2250  -13.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9290  -13.8895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2198  -12.6003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1869  -12.6149    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9939  -13.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9941  -12.6218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6952  -13.9114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8906  -12.1847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8894  -11.3266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5964  -10.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2967  -11.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2896  -12.2026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5862  -12.6246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6005  -10.0411    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.0052  -10.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6321  -13.4554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3361  -13.8807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4010  -13.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1024  -13.9118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 14  1  0
  6  7  2  0
  1  2  1  0
  7  8  1  0
 15 16  2  0
 15 17  1  0
  1 15  1  0
  5  4  1  0
 14 18  1  0
  8  9  2  0
 18 19  2  0
  4  1  2  0
 19 20  1  0
  9 10  1  0
 20 21  2  0
 10  5  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
  2  3  2  0
 20 24  1  0
  5  6  1  0
 21 25  1  0
 11 12  1  0
 12 26  1  0
 11 13  2  0
 26 27  1  0
  9 11  1  0
 17 28  1  0
  3  6  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA209149

   Diethyl 4-(3-bromo-4-methylphenylamino)quinoline-3,6-dicarboxylate

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: 457.32

Molecular Weight (Monoisotopic): 456.0685

AlogP: 5.40

#Rotatable Bonds: 6

Polar Surface Area: 77.52

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 5.21

CX LogP: 6.87

CX LogD: 6.87

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.50

Np Likeness Score: -1.16

References

1. Kim ND, Yoon J, Kim JH, Lee JT, Chon YS, Hwang MK, Ha I, Song WJ..  (2006)  Putative therapeutic agents for the learning and memory deficits of people with Down syndrome.,  16  (14): [PMID:16698266] [10.1016/j.bmcl.2006.04.042]

2. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays