1-Methyl-8-{[2-(phenylamino)phenyl]amino}-4,5-dihydro-1Hpyrazolo[4,3-h]quinazoline-3-carboxamide

ID: ALA1094820

PubChem CID: 46887138

Max Phase: Preclinical

Molecular Formula: C23H21N7O

Molecular Weight: 411.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1nc(C(N)=O)c2c1-c1nc(Nc3ccccc3Nc3ccccc3)ncc1CC2

Standard InChI:  InChI=1S/C23H21N7O/c1-30-21-16(20(29-30)22(24)31)12-11-14-13-25-23(28-19(14)21)27-18-10-6-5-9-17(18)26-15-7-3-2-4-8-15/h2-10,13,26H,11-12H2,1H3,(H2,24,31)(H,25,27,28)

Standard InChI Key:  JXRYPFSBKNWJBW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   21.1694  -23.1166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1682  -23.9440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8831  -24.3569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8813  -22.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5966  -23.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6000  -23.9415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0283  -23.1071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3085  -22.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0317  -23.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3142  -24.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4882  -25.1627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3133  -25.2478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.6491  -24.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3583  -24.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0767  -24.4765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.3504  -23.2459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4534  -24.3559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7393  -23.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7404  -23.1180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0271  -22.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3113  -23.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3133  -23.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0272  -24.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0708  -25.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0291  -25.1805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3156  -25.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6006  -25.1869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8958  -25.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8943  -26.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6095  -26.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3196  -26.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
 14 15  1  0
  5  8  1  0
 14 16  2  0
  6 10  1  0
  2 17  1  0
  9  7  1  0
 17 18  1  0
  7  8  1  0
 18 19  2  0
  9 10  2  0
 19 20  1  0
  5  4  2  0
 20 21  2  0
  4  1  1  0
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  5  6  1  0
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  2  3  1  0
 23 25  1  0
 10 11  1  0
 25 26  1  0
 11 12  1  0
 26 27  2  0
 12 13  2  0
 27 28  1  0
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 28 29  2  0
  3  6  2  0
 29 30  1  0
 13 14  1  0
 30 31  2  0
 31 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1094820

   8-(2-Anilinoanilino)-1-methyl-4,5-dihydropyrazolo[4,3-h]quinazoline-3-carboxamide

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: 411.47

Molecular Weight (Monoisotopic): 411.1808

AlogP: 3.56

#Rotatable Bonds: 5

Polar Surface Area: 110.75

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.50

CX Basic pKa: 1.68

CX LogP: 3.79

CX LogD: 3.79

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.46

Np Likeness Score: -1.02

References

1. Beria I, Ballinari D, Bertrand JA, Borghi D, Bossi RT, Brasca MG, Cappella P, Caruso M, Ceccarelli W, Ciavolella A, Cristiani C, Croci V, De Ponti A, Fachin G, Ferguson RD, Lansen J, Moll JK, Pesenti E, Posteri H, Perego R, Rocchetti M, Storici P, Volpi D, Valsasina B..  (2010)  Identification of 4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline derivatives as a new class of orally and selective Polo-like kinase 1 inhibitors.,  53  (9): [PMID:20397705] [10.1021/jm901713n]

Source

Source(1):

• Scientific Literature