N2-(4-chloro-2-methoxybenzyl)-N4-(5-ethyl-1H-pyrazol-3-yl)-5-methylquinazoline-2,4-diamine

ID: ALA4860332

PubChem CID: 164611998

Max Phase: Preclinical

Molecular Formula: C22H23ClN6O

Molecular Weight: 422.92

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1cc(Nc2nc(NCc3ccc(Cl)cc3OC)nc3cccc(C)c23)n[nH]1

Standard InChI:  InChI=1S/C22H23ClN6O/c1-4-16-11-19(29-28-16)26-21-20-13(2)6-5-7-17(20)25-22(27-21)24-12-14-8-9-15(23)10-18(14)30-3/h5-11H,4,12H2,1-3H3,(H3,24,25,26,27,28,29)

Standard InChI Key:  LURYOAGETDDIFD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   33.7188  -14.2716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7276  -13.4443    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.0166  -13.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0032  -14.6779    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.2916  -14.2621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2984  -13.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5869  -13.0178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8681  -13.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8653  -14.2560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5773  -14.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0223  -12.1999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.7396  -11.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4875  -12.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0438  -11.5266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6362  -10.8092    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.8280  -10.9754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.8636  -11.6185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3532  -10.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4295  -14.6905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.1477  -14.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8585  -14.7033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8486  -15.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5585  -15.9450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2776  -15.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2824  -14.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5718  -14.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9889  -15.9568    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   36.5753  -13.4695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.2915  -13.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5928  -12.1928    0.0000 C   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
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 24 27  1  0
 26 28  1  0
 28 29  1  0
  7 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4860332

   ---

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: 422.92

Molecular Weight (Monoisotopic): 422.1622

AlogP: 5.24

#Rotatable Bonds: 7

Polar Surface Area: 87.75

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.95

CX Basic pKa: 5.95

CX LogP: 5.92

CX LogD: 5.90

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.38

Np Likeness Score: -1.33

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