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

ID: ALA462626

PubChem CID: 24971060

Max Phase: Preclinical

Molecular Formula: C22H19N5O

Molecular Weight: 369.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(NC(=O)c2ccccc2)cc1Nc1nc(-c2cccnc2)c[nH]1

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

Standard InChI Key:  FARDRMIPGUAUFZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -2.1264   -4.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1276   -5.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4128   -5.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6963   -5.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6992   -4.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4146   -3.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8410   -3.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0188   -5.4882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7326   -5.0746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4477   -5.4860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7313   -4.2496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8424   -5.4893    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8430   -6.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5136   -6.7974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2593   -7.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4342   -7.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1788   -6.7984    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7410   -8.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5624   -8.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0477   -8.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7128   -9.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8878   -9.6646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4062   -8.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4443   -6.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1586   -6.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8734   -6.3070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8695   -5.4778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1546   -5.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
M  END

Alternative Forms

1. Parent:

   

   ALA462626

   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: 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: 4.04

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.47

Np Likeness Score: -1.60

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