1-(4-methyl-2,5-di(pyridin-4-yl)-1H-pyrrol-3-yl)ethanone

ID: ALA526901

PubChem CID: 9925594

Max Phase: Preclinical

Molecular Formula: C17H15N3O

Molecular Weight: 277.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)c1c(-c2ccncc2)[nH]c(-c2ccncc2)c1C

Standard InChI:  InChI=1S/C17H15N3O/c1-11-15(12(2)21)17(14-5-9-19-10-6-14)20-16(11)13-3-7-18-8-4-13/h3-10,20H,1-2H3

Standard InChI Key:  CFDCGXXHXUZSNP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    5.0880   -7.2692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9138   -7.2692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708   -6.4844    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5009   -5.9973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8353   -6.4844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4997   -5.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2159   -4.7582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2150   -3.9332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4986   -3.5207    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7817   -3.9390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7861   -4.7626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3969   -7.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0585   -8.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5424   -9.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3646   -9.2734    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7006   -8.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2148   -7.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0497   -6.2296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6018   -7.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7806   -7.8493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9367   -8.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  2  0
 11  6  1  0
  4  6  1  0
  1  2  2  0
 12 13  2  0
  6  7  2  0
 13 14  1  0
  2  3  1  0
 14 15  2  0
  7  8  1  0
 15 16  1  0
  3  4  1  0
 16 17  2  0
 17 12  1  0
  2 12  1  0
  8  9  2  0
  5 18  1  0
  4  5  2  0
  1 19  1  0
  9 10  1  0
 19 20  2  0
  5  1  1  0
 19 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA526901

   3-acetyl-4-methyl-2,5-di(4-pyridyl)-1H-pyrrole

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: 277.33

Molecular Weight (Monoisotopic): 277.1215

AlogP: 3.65

#Rotatable Bonds: 3

Polar Surface Area: 58.64

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.40

CX Basic pKa: 5.44

CX LogP: 1.82

CX LogD: 1.82

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.74

Np Likeness Score: -0.24

References

1. Bamborough P, Drewry D, Harper G, Smith GK, Schneider K..  (2008)  Assessment of chemical coverage of kinome space and its implications for kinase drug discovery.,  51  (24): [PMID:19035792] [10.1021/jm8011036]

2. Simon Townson and Suzanne Gokool. GlaxoSmithKline Published Kinase Inhibitor Set 2 Onchocerca lienalis Screening Data,  [10.6019/CHEMBL3988181]

3. Zarrinkar, Patrick P PP and 15 more authors.  2009-10-01  AC220 is a uniquely potent and selective inhibitor of FLT3 for the treatment of acute myeloid leukemia (AML).  [PMID:19654408]

4. Burgy, Guillaume G and 7 more authors.  2013-04  Chemical synthesis and biological validation of immobilized protein kinase inhibitory Leucettines.  [PMID:23454515]

5. Coombs, Thomas C and 8 more authors.  2013-06-15  Small-molecule pyrimidine inhibitors of the cdc2-like (Clk) and dual specificity tyrosine phosphorylation-regulated (Dyrk) kinases: development of chemical probe ML315.  [PMID:23642479]

6. Murár, Miroslav M and 5 more authors.  2017-01-27  Novel CLK1 inhibitors based on N-aryloxazol-2-amine skeleton - A possible way to dual VEGFR2 TK/CLK ligands.  [PMID:27940419]

7. Shi, Yihui and 5 more authors.  2017-02-01  A triple exon-skipping luciferase reporter assay identifies a new CLK inhibitor pharmacophore.  [PMID:28049589]

8. Totzke, Juliane J and 15 more authors.  2017-08-17  Takinib, a Selective TAK1 Inhibitor, Broadens the Therapeutic Efficacy of TNF-α Inhibition for Cancer and Autoimmune Disease.  [PMID:28820959]

9. Riggs, Jennifer R JR and 28 more authors.  2017-11-09  The Discovery of a Dual TTK Protein Kinase/CDC2-Like Kinase (CLK2) Inhibitor for the Treatment of Triple Negative Breast Cancer Initiated from a Phenotypic Screen.  [PMID:28991472]

10. Scott, James S JS and 24 more authors.  2017-12-28  Discovery and Optimization of Pyrrolopyrimidine Inhibitors of Interleukin-1 Receptor Associated Kinase 4 (IRAK4) for the Treatment of Mutant MYD88L265P Diffuse Large B-Cell Lymphoma.  [PMID:29172502]

11. Klaeger, Susan S and 47 more authors.  2017-12-01  The target landscape of clinical kinase drugs.  [PMID:29191878]

12. Brear, Paul and 9 more authors.  2018-07-15  Novel non-ATP competitive small molecules targeting the CK2 α/β interface.  [PMID:29759799]

13. Narayan, Satya S and 7 more authors.  2019-01-01  ASR352, A potent anticancer agent: Synthesis, preliminary SAR, and biological activities against colorectal cancer bulk, 5-fluorouracil/oxaliplatin resistant and stem cells.  [PMID:30384048]

14. Riggs, Jennifer R JR and 18 more authors.  2019-05-09  Design and Optimization Leading to an Orally Active TTK Protein Kinase Inhibitor with Robust Single Agent Efficacy.  [PMID:30998356]

Source

Source(2):

• Scientific Literature
• Published Kinase Inhibitor Set 2