Your company account is blocked and you cannot place orders. If you have questions, please contact your company administrator.

3-amino-7-methyl-2,5-diphenyl-2,4,5,7-tetrahydro-6H-pyrazolo[3,4-b]pyridin-6-one

ID: ALA5189885

PubChem CID: 168283263

Max Phase: Preclinical

Molecular Formula: C19H18N4O

Molecular Weight: 318.38

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  CN1C(=O)C(c2ccccc2)Cc2c1nn(-c1ccccc1)c2N

Standard InChI:  InChI=1S/C19H18N4O/c1-22-18-16(12-15(19(22)24)13-8-4-2-5-9-13)17(20)23(21-18)14-10-6-3-7-11-14/h2-11,15H,12,20H2,1H3

Standard InChI Key:  VPIBFZNNHAYAFZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   -1.5080    0.6140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5080   -0.2109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7959   -0.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0840   -0.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0840    0.6140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7959    1.0308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6972    0.8677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1802    0.2032    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6971   -0.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9521   -1.2460    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2238    1.0244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7959    1.8524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2196   -0.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2199   -1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9297   -1.8524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6414   -1.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6430   -0.6238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9342   -0.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0018    0.2032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4128    0.9147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2320    0.9139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6430    0.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2355   -0.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4143   -0.5112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  5  4  1  0
  5  6  1  0
  1  6  1  0
  7  5  2  0
  8  7  1  0
  9  8  1  0
  4  9  2  0
  9 10  1  0
  1 11  2  0
  6 12  1  0
 13  2  1  0
 14 13  2  0
 15 14  1  0
 16 15  2  0
 17 16  1  0
 13 18  1  0
 18 17  2  0
 19  8  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
 23 22  1  0
 19 24  1  0
 24 23  2  0
M  END

Alternative Forms

  1. Parent:

    ALA5189885

    ---

Associated Targets(Human)

MKNK2 Tchem MAP kinase-interacting serine/threonine-protein kinase 1/2 (155 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Topical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Biocomponents

Calculated Properties

Molecular Weight: 318.38Molecular Weight (Monoisotopic): 318.1481AlogP: 2.76#Rotatable Bonds: 2
Polar Surface Area: 64.15Molecular Species: NEUTRALHBA: 4HBD: 1
#RO5 Violations: HBA (Lipinski): 5HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 1.84CX LogP: 3.00CX LogD: 3.00
Aromatic Rings: 3Heavy Atoms: 24QED Weighted: 0.79Np Likeness Score: -0.61

References

1. Bou-Petit E, Hümmer S, Alarcon H, Slobodnyuk K, Cano-Galietero M, Fuentes P, Guijarro PJ, Muñoz MJ, Suarez-Cabrera L, Santamaria A, Estrada-Tejedor R, Borrell JI, Ramón Y Cajal S..  (2022)  Overcoming Paradoxical Kinase Priming by a Novel MNK1 Inhibitor.,  65  (8.0): [PMID:35417652] [10.1021/acs.jmedchem.1c01941]
2. 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]
3. Oyarzabal, Julen J and 12 more authors.  2010-09-23  Discovery of mitogen-activated protein kinase-interacting kinase 1 inhibitors by a comprehensive fragment-oriented virtual screening approach.  [PMID:20722422]
4. Teo, Theodosia T and 11 more authors.  2015-10-20  An integrated approach for discovery of highly potent and selective Mnk inhibitors: Screening, synthesis and SAR analysis.  [PMID:26408454]
5. Han, Wooseok W and 12 more authors.  2016-04-14  Discovery of a Selective and Potent Inhibitor of Mitogen-Activated Protein Kinase-Interacting Kinases 1 and 2 (MNK1/2) Utilizing Structure-Based Drug Design.  [PMID:27002243]
6. Cherian, Joseph J and 24 more authors.  2016-04-14  Structure-Activity Relationship Studies of Mitogen Activated Protein Kinase Interacting Kinase (MNK) 1 and 2 and BCR-ABL1 Inhibitors Targeting Chronic Myeloid Leukemic Cells.  [PMID:27011159]
7. Farag, Ahmed Karam AK and 5 more authors.  2017-12-01  Novel LCK/FMS inhibitors based on phenoxypyrimidine scaffold as potential treatment for inflammatory disorders.  [PMID:29107425]
8. Reich, Siegfried H SH and 28 more authors.  2018-04-26  Structure-based Design of Pyridone-Aminal eFT508 Targeting Dysregulated Translation by Selective Mitogen-activated Protein Kinase Interacting Kinases 1 and 2 (MNK1/2) Inhibition.  [PMID:29526098]
9. Yang, Haiyan H and 32 more authors.  2018-05-24  Optimization of Selective Mitogen-Activated Protein Kinase Interacting Kinases 1 and 2 Inhibitors for the Treatment of Blast Crisis Leukemia.  [PMID:29683667]
10. 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]
11. Yuan, Xinrui X and 5 more authors.  2019-04-01  Design, synthesis and biological evaluation of pyridone-aminal derivatives as MNK1/2 inhibitors.  [PMID:30824167]
12. Abdelaziz, Ahmed M AM and 8 more authors.  2019-09-15  Synthesis and evaluation of 2'H-spiro[cyclohexane-1,3'-imidazo[1,5-a]pyridine]-1',5'-dione derivatives as Mnk inhibitors.  [PMID:31362920]
13. Kwiatkowski, Jacek and 25 more authors.  2020-01-23  Stepwise Evolution of Fragment Hits against MAPK Interacting Kinases 1 and 2.  [PMID:31910010]

Source