ethyl 1-methyl-8-(phenylamino)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

ID: ALA1098059

PubChem CID: 44232942

Max Phase: Preclinical

Molecular Formula: C19H19N5O2

Molecular Weight: 349.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1nn(C)c2c1CCc1cnc(Nc3ccccc3)nc1-2

Standard InChI:  InChI=1S/C19H19N5O2/c1-3-26-18(25)16-14-10-9-12-11-20-19(21-13-7-5-4-6-8-13)22-15(12)17(14)24(2)23-16/h4-8,11H,3,9-10H2,1-2H3,(H,20,21,22)

Standard InChI Key:  XCLOVJZYWDYYRT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   16.7304   -7.3748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7293   -8.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4436   -8.6143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4418   -6.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1568   -7.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1602   -8.1992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5876   -7.3653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8682   -6.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5910   -8.1933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8739   -8.6091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0479   -9.4197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8725   -9.5047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2080   -8.7468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9169   -8.3284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6348   -8.7339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9090   -7.5040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0149   -8.6133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3011   -8.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3022   -7.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5893   -6.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8739   -7.3752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8759   -8.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5894   -8.6129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6307  -10.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6427   -9.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3607   -9.9637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
 12 13  2  0
 13  9  1  0
  3  6  2  0
 13 14  1  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
 21 22  1  0
  5  6  1  0
 22 23  2  0
 23 18  1  0
 11 24  1  0
  2  3  1  0
 15 25  1  0
 10 11  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1098059

   ethyl 8-anilino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

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: 349.39

Molecular Weight (Monoisotopic): 349.1539

AlogP: 2.90

#Rotatable Bonds: 4

Polar Surface Area: 81.93

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.74

CX Basic pKa: 1.71

CX LogP: 3.66

CX LogD: 3.66

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.73

Np Likeness Score: -1.17

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]

2. Zhao H, Hu X, Cao K, Zhang Y, Zhao K, Tang C, Feng B..  (2018)  Synthesis and SAR of 4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline derivatives as potent and selective CDK4/6 inhibitors.,  157  [PMID:30165341] [10.1016/j.ejmech.2018.08.043]

Source

Source(1):

• Scientific Literature