(E)-1-(4-Chlorophenyl)-3-(3-((7-chloroquinolin-4-yl)amino)phenyl)prop-2-en-1-one

ID: ALA4080733

PubChem CID: 137648301

Max Phase: Preclinical

Molecular Formula: C24H16Cl2N2O

Molecular Weight: 419.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1cccc(Nc2ccnc3cc(Cl)ccc23)c1)c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C24H16Cl2N2O/c25-18-7-5-17(6-8-18)24(29)11-4-16-2-1-3-20(14-16)28-22-12-13-27-23-15-19(26)9-10-21(22)23/h1-15H,(H,27,28)/b11-4+

Standard InChI Key:  KMDJTHSSASRYFL-NYYWCZLTSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    8.6286   -4.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6275   -5.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3396   -5.5827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3379   -3.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0506   -4.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0514   -5.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7599   -5.5767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4723   -5.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4676   -4.3396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7543   -3.9321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7500   -3.1108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4596   -2.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1691   -3.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8782   -2.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8743   -1.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1554   -1.4641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4491   -1.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5920   -3.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9153   -5.5818    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.3019   -2.6882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0157   -3.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7255   -2.6814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0196   -3.9147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4320   -3.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1413   -2.6775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1378   -1.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4191   -1.4462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7167   -1.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8471   -1.4382    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 14 18  1  0
  2 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 22  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4080733

   ---

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: 419.31

Molecular Weight (Monoisotopic): 418.0640

AlogP: 7.18

#Rotatable Bonds: 5

Polar Surface Area: 41.99

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 6.46

CX LogP: 6.70

CX LogD: 6.65

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.28

Np Likeness Score: -0.86

References

1. Ramírez-Prada J, Robledo SM, Vélez ID, Crespo MDP, Quiroga J, Abonia R, Montoya A, Svetaz L, Zacchino S, Insuasty B..  (2017)  Synthesis of novel quinoline-based 4,5-dihydro-1H-pyrazoles as potential anticancer, antifungal, antibacterial and antiprotozoal agents.,  131  [PMID:28329730] [10.1016/j.ejmech.2017.03.016]

2. de Mello MVP, Abrahim-Vieira BA, Domingos TFS, de Jesus JB, de Sousa ACC, Rodrigues CR, Souza AMT..  (2018)  A comprehensive review of chalcone derivatives as antileishmanial agents.,  150  [PMID:29602038] [10.1016/j.ejmech.2018.03.047]

Source

Source(1):

• Scientific Literature