6-chloro-N-((4,4-difluorocyclohexyl)methyl)-2-(2-methoxyethylamino)quinoline-5-carboxamide

ID: ALA4474419

PubChem CID: 118566610

Max Phase: Preclinical

Molecular Formula: C20H24ClF2N3O2

Molecular Weight: 411.88

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COCCNc1ccc2c(C(=O)NCC3CCC(F)(F)CC3)c(Cl)ccc2n1

Standard InChI:  InChI=1S/C20H24ClF2N3O2/c1-28-11-10-24-17-5-2-14-16(26-17)4-3-15(21)18(14)19(27)25-12-13-6-8-20(22,23)9-7-13/h2-5,13H,6-12H2,1H3,(H,24,26)(H,25,27)

Standard InChI Key:  FSZBWUFOVGIKHN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    6.1374  -11.5165    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.7290  -12.2331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5539  -12.2285    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.1694  -15.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1682  -16.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8830  -17.1899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8812  -15.5369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5966  -15.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5974  -16.7729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3127  -17.1839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0277  -16.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0229  -15.9391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3070  -15.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4548  -15.5374    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8787  -14.7119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5919  -14.2973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5895  -13.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3028  -13.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1630  -14.3016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0171  -13.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7282  -13.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0145  -11.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2971  -12.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7437  -17.1788    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4566  -16.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1727  -17.1733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8855  -16.7580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6016  -17.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  4 14  1  0
  7 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 15 19  2  0
 18 20  1  0
 18 23  1  0
 20 21  1  0
 21  2  1  0
  2 22  1  0
 22 23  1  0
 11 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4474419

   6-Chloro-2-(2-methoxy-ethylamino)-quinoline-5-carboxylic acid (4,4-difluoro-cyclohexyl methyl)-amide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 411.88

Molecular Weight (Monoisotopic): 411.1525

AlogP: 4.50

#Rotatable Bonds: 7

Polar Surface Area: 63.25

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.75

CX LogP: 3.43

CX LogD: 3.43

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.66

Np Likeness Score: -1.22

References

1. Xiao Y, Karra S, Goutopoulos A, Morse NT, Zhang S, Dhanabal M, Tian H, Seenisamy J, Jayadevan J, Caldwell R, Potnick J, Bleich M, Chekler E, Sherer B, Sriraman V..  (2019)  Synthesis and SAR development of quinoline analogs as novel P2X7 receptor antagonists.,  29  (13): [PMID:31031055] [10.1016/j.bmcl.2019.04.033]

Source

Source(1):

• Scientific Literature