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

ID: ALA4856820

PubChem CID: 164613571

Max Phase: Preclinical

Molecular Formula: C20H19FN6

Molecular Weight: 362.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1cc(Nc2nc(NCc3ccc(F)cc3)nc3ccccc23)n[nH]1

Standard InChI:  InChI=1S/C20H19FN6/c1-2-15-11-18(27-26-15)24-19-16-5-3-4-6-17(16)23-20(25-19)22-12-13-7-9-14(21)10-8-13/h3-11H,2,12H2,1H3,(H3,22,23,24,25,26,27)

Standard InChI Key:  MYVXPLSILQDDFA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   30.1355   -5.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1442   -5.1400    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.4332   -4.7206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4198   -6.3736    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.7082   -5.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7151   -5.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0036   -4.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2847   -5.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2818   -5.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9940   -6.3655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4389   -3.8956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.1562   -3.4881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9041   -3.8317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4604   -3.2223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0527   -2.5050    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.2447   -2.6711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.2803   -3.3142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7698   -2.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8462   -6.3863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.5643   -5.9802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2751   -6.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2652   -7.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9751   -7.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6943   -7.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6990   -6.4054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9885   -5.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4055   -7.6525    0.0000 F   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
M  END

Alternative Forms

1. Parent:

   

   ALA4856820

   ---

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: 362.41

Molecular Weight (Monoisotopic): 362.1655

AlogP: 4.41

#Rotatable Bonds: 6

Polar Surface Area: 78.52

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.95

CX Basic pKa: 5.44

CX LogP: 5.10

CX LogD: 5.09

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.47

Np Likeness Score: -1.57

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. Wu T, Qin Q, Lv R, Liu N, Yin W, Hao C, Sun Y, Zhang C, Sun Y, Zhao D, Cheng M..  (2022)  Discovery of quinazoline derivatives CZw-124 as a pan-TRK inhibitor with potent anticancer effects in vitro and in vivo.,  238  [PMID:35617855] [10.1016/j.ejmech.2022.114451]

3. 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