(E)-N-(7-chloroquinolin-4-yl)-3-(4-isopropylphenyl)acrylamide

ID: ALA2042192

PubChem CID: 66573729

Max Phase: Preclinical

Molecular Formula: C21H19ClN2O

Molecular Weight: 350.85

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H19ClN2O/c1-14(2)16-6-3-15(4-7-16)5-10-21(25)24-19-11-12-23-20-13-17(22)8-9-18(19)20/h3-14H,1-2H3,(H,23,24,25)/b10-5+

Standard InChI Key:  DQUFEXPOFYGTFS-BJMVGYQFSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    7.9015   -1.6510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6182   -2.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3305   -1.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0471   -2.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0515   -2.8771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7682   -3.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4760   -2.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7594   -1.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8972   -0.8260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1893   -2.0673    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2024   -4.5422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9147   -4.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9103   -3.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1937   -2.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4814   -3.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7647   -2.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0525   -3.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0568   -4.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7735   -4.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4858   -4.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3446   -4.5574    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.4804   -2.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1971   -3.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2015   -4.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9093   -2.8618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6 22  1  0
 22  7  2  0
  7  8  1  0
  4  8  2  0
  1  9  2  0
  1 10  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 11 20  1  0
 15 20  1  0
 18 21  1  0
 10 14  1  0
 22 23  1  0
  1  2  1  0
 23 24  1  0
  2  3  2  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2042192

   (E)-N-(7-chloro-4-quinolyl)-3-(4-isopropylphenyl)prop-2-enamide

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: 350.85

Molecular Weight (Monoisotopic): 350.1186

AlogP: 5.66

#Rotatable Bonds: 4

Polar Surface Area: 41.99

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.45

CX Basic pKa: 4.21

CX LogP: 5.58

CX LogD: 5.58

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.62

Np Likeness Score: -0.99

References

1. Pérez BC, Teixeira C, Figueiras M, Gut J, Rosenthal PJ, Gomes JR, Gomes P..  (2012)  Novel cinnamic acid/4-aminoquinoline conjugates bearing non-proteinogenic amino acids: towards the development of potential dual action antimalarials.,  54  [PMID:22683112] [10.1016/j.ejmech.2012.05.022]

Source

Source(1):

• Scientific Literature