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

ID: ALA473116

PubChem CID: 24971208

Max Phase: Preclinical

Molecular Formula: C22H19N5O

Molecular Weight: 369.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C(=O)Nc2cccc(Nc3nc(-c4cccnc4)c[nH]3)c2)cc1

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

Standard InChI Key:  GPYPGGOBTAEZTK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   11.7569    3.5084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7557    2.6810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4706    2.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1870    2.6815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1841    3.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4688    3.9211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9021    2.2701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6159    2.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3311    2.2723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6146    3.5087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0409    2.2691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0403    1.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3697    0.9610    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6241    0.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4491    0.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7045    0.9599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1423   -0.4888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3209   -0.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8357   -1.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1706   -1.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9955   -1.9063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4771   -1.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3277    1.4489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7568    1.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7528    2.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0380    2.6881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0375    1.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4701    1.0368    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
 23 27  1  0
  5  6  2  0
 11 12  1  0
 24 25  1  0
 12 13  2  0
 25 26  2  0
 26  9  1  0
  6  1  1  0
 24 27  2  0
  1  2  2  0
 24 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA473116

   4-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: -1.56

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