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

ID: ALA516043

PubChem CID: 24971161

Max Phase: Preclinical

Molecular Formula: C22H18ClN5O

Molecular Weight: 403.87

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H18ClN5O/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,1H3,(H,26,29)(H2,25,27,28)

Standard InChI Key:  ZPFPYBQNDGANTR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    9.2736  -11.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2724  -11.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9872  -12.2735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7037  -11.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7008  -11.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9854  -10.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5590  -10.6210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4188  -12.2716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1326  -11.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8477  -12.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1313  -11.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5576  -12.2726    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5570  -13.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8864  -13.5807    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1407  -14.3655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9658  -14.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2212  -13.5818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6590  -15.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8376  -14.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3523  -15.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6872  -16.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5122  -16.4479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9938  -15.7807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8443  -13.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5586  -13.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2734  -13.0904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2695  -12.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5546  -11.8535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9891  -13.5008    0.0000 Cl  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:

   

   ALA516043

   4-chloro-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: 403.87

Molecular Weight (Monoisotopic): 403.1200

AlogP: 5.43

#Rotatable Bonds: 5

Polar Surface Area: 82.70

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.14

CX Basic pKa: 7.53

CX LogP: 5.00

CX LogD: 4.65

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.41

Np Likeness Score: -1.76

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