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

ID: ALA462643

PubChem CID: 24971112

Max Phase: Preclinical

Molecular Formula: C23H21N5O

Molecular Weight: 383.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C(=O)Nc2ccc(C)c(Nc3nc(-c4cccnc4)c[nH]3)c2)cc1

Standard InChI:  InChI=1S/C23H21N5O/c1-15-5-8-17(9-6-15)22(29)26-19-10-7-16(2)20(12-19)27-23-25-14-21(28-23)18-4-3-11-24-13-18/h3-14H,1-2H3,(H,26,29)(H2,25,27,28)

Standard InChI Key:  RMVKDVBFQNQPJD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   10.9152  -18.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9141  -19.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6289  -19.8360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3453  -19.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3425  -18.5922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6271  -18.1830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2007  -18.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0605  -19.8341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7743  -19.4204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4894  -19.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7730  -18.5954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1993  -19.8351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1986  -20.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5281  -21.1432    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7824  -21.9280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6075  -21.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8629  -21.1443    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3007  -22.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4793  -22.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9940  -23.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3289  -23.9257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1538  -24.0104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6355  -23.3432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4860  -20.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2003  -21.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9151  -20.6529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9111  -19.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1963  -19.4160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6308  -21.0633    0.0000 C   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:

   

   ALA462643

   4-methyl-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: 383.46

Molecular Weight (Monoisotopic): 383.1746

AlogP: 5.08

#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: 4.91

CX LogD: 4.56

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.45

Np Likeness Score: -1.66

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]

2. 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