4-[4-(4-Fluorophenyl)-5-(2-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-imidazol-2-yl]phenol

ID: ALA2179119

PubChem CID: 136236302

Max Phase: Preclinical

Molecular Formula: C28H19FN4O

Molecular Weight: 446.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1ccc(-c2nc(-c3ccc(F)cc3)c(-c3ccnc4[nH]c(-c5ccccc5)cc34)[nH]2)cc1

Standard InChI:  InChI=1S/C28H19FN4O/c29-20-10-6-18(7-11-20)25-26(33-27(32-25)19-8-12-21(34)13-9-19)22-14-15-30-28-23(22)16-24(31-28)17-4-2-1-3-5-17/h1-16,34H,(H,30,31)(H,32,33)

Standard InChI Key:  HFDJAPMETZJFMI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 39  0  0  0  0  0  0  0  0999 V2000
    4.6341  -10.0070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4139   -9.7626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4243   -8.9453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6475   -8.6836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1631   -9.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1163   -8.5168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8354   -8.9073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5310   -8.4798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5087   -7.6621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7849   -7.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0923   -7.7033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3488   -9.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9479   -8.6209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1315   -8.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7151   -9.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1209  -10.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9360  -10.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1204  -10.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5363  -10.9832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5320  -10.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8237   -9.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8284  -11.3933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1202  -10.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5124  -11.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8450  -12.2787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6583  -12.1932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2042   -7.2330    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.4385  -12.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6202  -12.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2117  -13.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6203  -14.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4417  -14.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8466  -13.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8979   -9.3095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  1  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  3  6  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  5 12  1  0
 18 23  2  0
 22 19  2  0
 19 20  1  0
 20 21  2  0
 21 18  1  0
  2 18  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 22  1  0
  9 27  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
 25 28  1  0
 15 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2179119

   ---

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: 446.49

Molecular Weight (Monoisotopic): 446.1543

AlogP: 6.80

#Rotatable Bonds: 4

Polar Surface Area: 77.59

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.64

CX Basic pKa: 4.87

CX LogP: 6.13

CX LogD: 6.13

Aromatic Rings: 6

Heavy Atoms: 34

QED Weighted: 0.28

Np Likeness Score: -0.61

References

1. Selig R, Goettert M, Schattel V, Schollmeyer D, Albrecht W, Laufer S..  (2012)  A frozen analogue approach to aminopyridinylimidazoles leading to novel and promising p38 MAP kinase inhibitors.,  55  (19): [PMID:22951114] [10.1021/jm300852w]

2. Juchum M, Günther M, Döring E, Sievers-Engler A, Lämmerhofer M, Laufer S..  (2017)  Trisubstituted Imidazoles with a Rigidized Hinge Binding Motif Act As Single Digit nM Inhibitors of Clinically Relevant EGFR L858R/T790M and L858R/T790M/C797S Mutants: An Example of Target Hopping.,  60  (11): [PMID:28482151] [10.1021/acs.jmedchem.7b00178]

3. Shaikh M, Shinde Y, Pawara R, Noolvi M, Surana S, Ahmad I, Patel H..  (2022)  Emerging Approaches to Overcome Acquired Drug Resistance Obstacles to Osimertinib in Non-Small-Cell Lung Cancer.,  65  (2.0): [PMID:34323489] [10.1021/acs.jmedchem.1c00876]

Source

Source(1):

• Scientific Literature