(rac)-1-(4-chlorophenyl)-6,7-diethoxy-2-(4-methoxyphenyl)-1,2-dihydroisoquinolin-3(4H)-one

ID: ALA3604658

PubChem CID: 5037958

Max Phase: Preclinical

Molecular Formula: C26H26ClNO4

Molecular Weight: 451.95

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1cc2c(cc1OCC)C(c1ccc(Cl)cc1)N(c1ccc(OC)cc1)C(=O)C2

Standard InChI:  InChI=1S/C26H26ClNO4/c1-4-31-23-14-18-15-25(29)28(20-10-12-21(30-3)13-11-20)26(17-6-8-19(27)9-7-17)22(18)16-24(23)32-5-2/h6-14,16,26H,4-5,15H2,1-3H3

Standard InChI Key:  ICXBLIHPEQODQG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8911    1.5017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890    3.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8911   -1.5017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0099   -3.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0151   -5.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5882   -3.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2770   -7.1982    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.9086   -1.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9097   -3.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2093   -3.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5078   -3.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5067   -1.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2071   -0.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8096   -3.7478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8475   -3.1456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9270    3.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9270   -3.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
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  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 11 12  1  0
  9 11  1  0
 13 14  1  0
  8 13  1  0
  1 15  2  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  3 16  1  0
 19 22  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
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 27 28  2  0
 28 23  1  0
  2 23  1  0
 29 30  1  0
 26 29  1  0
 12 31  1  0
 14 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3604658

   1-(4-chlorophenyl)-6,7-diethoxy-2-(4-methoxyphenyl)-1,4-dihydroisoquinolin-3(2H)-one

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: 451.95

Molecular Weight (Monoisotopic): 451.1550

AlogP: 5.82

#Rotatable Bonds: 7

Polar Surface Area: 48.00

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.29

CX LogD: 5.29

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.45

Np Likeness Score: -0.62

References

1. Gessier F, Kallen J, Jacoby E, Chène P, Stachyra-Valat T, Ruetz S, Jeay S, Holzer P, Masuya K, Furet P..  (2015)  Discovery of dihydroisoquinolinone derivatives as novel inhibitors of the p53-MDM2 interaction with a distinct binding mode.,  25  (17): [PMID:26141769] [10.1016/j.bmcl.2015.06.058]

Source

Source(1):

• Scientific Literature