N2-(4-chlorobenzyl)-N4-(5-ethyl-1H-pyrazol-3-yl)-5-methoxyquinazoline-2,4-diamine

ID: ALA4874424

PubChem CID: 164627176

Max Phase: Preclinical

Molecular Formula: C21H21ClN6O

Molecular Weight: 408.89

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1cc(Nc2nc(NCc3ccc(Cl)cc3)nc3cccc(OC)c23)n[nH]1

Standard InChI:  InChI=1S/C21H21ClN6O/c1-3-15-11-18(28-27-15)25-20-19-16(5-4-6-17(19)29-2)24-21(26-20)23-12-13-7-9-14(22)10-8-13/h4-11H,3,12H2,1-2H3,(H3,23,24,25,26,27,28)

Standard InChI Key:  GHDFCDSHKKEZJV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   31.3141   -5.4215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3229   -4.5942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6119   -4.1747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5985   -5.8276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8869   -5.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8938   -4.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1823   -4.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4635   -4.5758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4606   -5.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1727   -5.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6176   -3.3497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.3349   -2.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0828   -3.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6391   -2.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2314   -1.9591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.4234   -2.1252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.4589   -2.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9485   -2.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0249   -5.8404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.7430   -5.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4538   -5.8532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1881   -3.3426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4766   -2.9251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4439   -6.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1537   -7.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8729   -6.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8777   -5.8594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1671   -5.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5841   -7.1066    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
  3 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 12  2  0
 14 17  1  0
 17 18  1  0
  1 19  1  0
 19 20  1  0
 20 21  1  0
  7 22  1  0
 22 23  1  0
 21 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 21  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4874424

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 408.89

Molecular Weight (Monoisotopic): 408.1465

AlogP: 4.93

#Rotatable Bonds: 7

Polar Surface Area: 87.75

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.24

CX Basic pKa: 6.07

CX LogP: 5.40

CX LogD: 5.38

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.40

Np Likeness Score: -1.22

References

1. Uehling DE, Joseph B, Chung KC, Zhang AX, Ler S, Prakesch MA, Poda G, Grouleff J, Aman A, Kiyota T, Leung-Hagesteijn C, Konda JD, Marcellus R, Griffin C, Subramaniam R, Abibi A, Strathdee CA, Isaac MB, Al-Awar R, Tiedemann RE..  (2021)  Design, Synthesis, and Characterization of 4-Aminoquinazolines as Potent Inhibitors of the G Protein-Coupled Receptor Kinase 6 (GRK6) for the Treatment of Multiple Myeloma.,  64  (15.0): [PMID:34291633] [10.1021/acs.jmedchem.1c00506]

2. Tesmer, John J G JJ, Tesmer, Valerie M VM, Lodowski, David T DT, Steinhagen, Henning H and Huber, Jochen J.  2010-02-25  Structure of human G protein-coupled receptor kinase 2 in complex with the kinase inhibitor balanol.  [PMID:20128603]

Source

Source(1):

• Scientific Literature