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

ID: ALA472921

PubChem CID: 24971207

Max Phase: Preclinical

Molecular Formula: C22H19N5O

Molecular Weight: 369.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc(C(=O)Nc2cccc(Nc3nc(-c4cccnc4)c[nH]3)c2)c1

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

Standard InChI Key:  RXNJNCJKYXUTGK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    4.3569    3.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3557    2.4352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0706    2.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7870    2.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7841    3.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0688    3.6753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5021    2.0243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2159    2.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9311    2.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2146    3.2629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6409    2.0232    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6403    1.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9697    0.7151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2241   -0.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0491   -0.0704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3045    0.7141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7423   -0.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9209   -0.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4357   -1.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7706   -2.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5955   -2.1521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0771   -1.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9277    1.2031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6420    0.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3568    1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3528    2.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6380    2.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0652    2.4509    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
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA472921

   3-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: -1.67

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