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

ID: ALA473123

PubChem CID: 24971160

Max Phase: Preclinical

Molecular Formula: C22H18N6O3

Molecular Weight: 414.43

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H18N6O3/c1-14-4-7-17(25-21(29)15-5-8-18(9-6-15)28(30)31)11-19(14)26-22-24-13-20(27-22)16-3-2-10-23-12-16/h2-13H,1H3,(H,25,29)(H2,24,26,27)

Standard InChI Key:  WGVUYCIHJGHBLJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   -1.8723  -11.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8734  -12.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1586  -12.6610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4422  -12.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4450  -11.4172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1604  -11.0080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5868  -11.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2730  -12.6591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9868  -12.2454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7019  -12.6568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9855  -11.4204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5882  -12.6601    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5889  -13.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2594  -13.9682    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0051  -14.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1800  -14.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9246  -13.9693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4868  -15.4179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3082  -15.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7935  -15.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4586  -16.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6337  -16.8354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1520  -16.1682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6985  -13.4803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4128  -13.8916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1276  -13.4779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1236  -12.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4088  -12.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8433  -13.8883    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5585  -13.4736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8476  -14.7132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
  1  7  1  0
  3  4  2  0
 29 30  2  0
 29 31  1  0
M  CHG  2  29   1  31  -1
M  END

Alternative Forms

1. Parent:

   

   ALA473123

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

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: 414.43

Molecular Weight (Monoisotopic): 414.1440

AlogP: 4.68

#Rotatable Bonds: 6

Polar Surface Area: 125.84

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.11

CX Basic pKa: 7.53

CX LogP: 4.34

CX LogD: 3.98

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.31

Np Likeness Score: -1.80

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