4-Amino-N-(4-methyl-3-(4-(pyridin-3-yl)-1H-imidazol-2-ylamino)phenyl)benzamide

ID: ALA472920

PubChem CID: 24971164

Max Phase: Preclinical

Molecular Formula: C22H20N6O

Molecular Weight: 384.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(NC(=O)c2ccc(N)cc2)cc1Nc1nc(-c2cccnc2)c[nH]1

Standard InChI:  InChI=1S/C22H20N6O/c1-14-4-9-18(26-21(29)15-5-7-17(23)8-6-15)11-19(14)27-22-25-13-20(28-22)16-3-2-10-24-12-16/h2-13H,23H2,1H3,(H,26,29)(H2,25,27,28)

Standard InChI Key:  RGUKLBRRWMZXQX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   10.2736  -17.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2724  -17.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9872  -18.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7037  -17.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7008  -16.9963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9854  -16.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5590  -16.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4188  -18.2382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1326  -17.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8477  -18.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1313  -16.9996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5576  -18.2393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5570  -19.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8864  -19.5474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1407  -20.3322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9658  -20.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2212  -19.5484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6590  -20.9971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8376  -20.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3523  -21.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6872  -22.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5122  -22.4146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9938  -21.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8443  -19.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5586  -19.4707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2734  -19.0570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2695  -18.2278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5546  -17.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9891  -19.4675    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0
  3  4  2  0
  4  8  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 13  1  0
  8  9  1  0
 18 19  2  0
  4  5  1  0
 19 20  1  0
  9 10  1  0
 20 21  2  0
  2  3  1  0
 21 22  1  0
  9 11  2  0
 22 23  2  0
 23 18  1  0
 15 18  1  0
  5  6  2  0
 10 24  2  0
  2 12  1  0
 24 25  1  0
  6  1  1  0
 25 26  2  0
 12 13  1  0
 26 27  1  0
 13 14  2  0
 27 28  2  0
 28 10  1  0
  1  2  2  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA472920

   4-amino-N-[4-methyl-3-[(5-pyridin-3-yl-1H-imidazol-2-yl)amino]phenyl]benzamide

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: 384.44

Molecular Weight (Monoisotopic): 384.1699

AlogP: 4.36

#Rotatable Bonds: 5

Polar Surface Area: 108.72

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.14

CX Basic pKa: 7.53

CX LogP: 3.57

CX LogD: 3.22

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.38

Np Likeness Score: -1.54

References

1. Mahboobi S, Sellmer A, Eswayah A, Elz S, Uecker A, Böhmer FD..  (2008)  Inhibition of PDGFR tyrosine kinase activity by a series of novel N-(3-(4-(pyridin-3-yl)-1H-imidazol-2-ylamino)phenyl)amides: a SAR study on the bioisosterism of pyrimidine and imidazole.,  43  (7): [PMID:17983688] [10.1016/j.ejmech.2007.09.021]

Source

Source(1):

• Scientific Literature