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

ID: ALA514457

PubChem CID: 24971165

Max Phase: Preclinical

Molecular Formula: C22H19N5O

Molecular Weight: 369.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccccc1C(=O)Nc1cccc(Nc2nc(-c3cccnc3)c[nH]2)c1

Standard InChI:  InChI=1S/C22H19N5O/c1-15-6-2-3-10-19(15)21(28)25-17-8-4-9-18(12-17)26-22-24-14-20(27-22)16-7-5-11-23-13-16/h2-14H,1H3,(H,25,28)(H2,24,26,27)

Standard InChI Key:  KJBQDKWAFOVXMX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   -2.9764    3.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9776    2.2727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2628    1.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5463    2.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5492    3.1037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2646    3.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8312    1.8618    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1174    2.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5977    1.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1187    3.1004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6924    1.8607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6930    1.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3636    0.5526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1093   -0.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2842   -0.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0288    0.5516    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5910   -0.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4124   -0.8088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8977   -1.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5628   -2.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7378   -2.3146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2562   -1.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5943    1.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3086    0.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0234    1.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195    1.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3046    2.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2991    3.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  7  1  0
  3  4  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 12  1  0
  7  8  1  0
 17 18  2  0
  8  9  1  0
 18 19  1  0
  4  5  1  0
 19 20  2  0
  8 10  2  0
 20 21  1  0
  2  3  1  0
 21 22  2  0
 22 17  1  0
 14 17  1  0
  2 11  1  0
  9 23  2  0
  5  6  2  0
 23 24  1  0
 11 12  1  0
 24 25  2  0
 12 13  2  0
 25 26  1  0
  6  1  1  0
 26 27  2  0
 27  9  1  0
  1  2  2  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA514457

   2-methyl-N-[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: 369.43

Molecular Weight (Monoisotopic): 369.1590

AlogP: 4.78

#Rotatable Bonds: 5

Polar Surface Area: 82.70

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.14

CX Basic pKa: 7.53

CX LogP: 4.40

CX LogD: 4.05

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.47

Np Likeness Score: -1.64

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