1-(2-chlorophenyl)-6-(3,3,3-trifluoro-2-methylpropyl)-1H-pyrazolo[3,4-d]pyrimidine-4(5H)-one

ID: ALA1513993

Chembl Id: CHEMBL1513993

Max Phase: Preclinical

Molecular Formula: C15H12ClF3N4O

Molecular Weight: 356.74

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: BAY-736691

Canonical SMILES:  C[C@H](Cc1nc2c(cnn2-c2ccccc2Cl)c(=O)[nH]1)C(F)(F)F

Standard InChI:  InChI=1S/C15H12ClF3N4O/c1-8(15(17,18)19)6-12-21-13-9(14(24)22-12)7-20-23(13)11-5-3-2-4-10(11)16/h2-5,7-8H,6H2,1H3,(H,21,22,24)/t8-/m1/s1

Standard InChI Key:  FFPXPXOAFQCNBS-MRVPVSSYSA-N

Alternative Forms

  1. Parent:

    ALA1513993

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Associated Targets(Human)

THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
VDR Tclin Vitamin D receptor (26531 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PDE9A Tchem Phosphodiesterase 9A (1131 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PDE1B Tclin Phosphodiesterase 1B (178 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

rep Replicase polyprotein 1ab (11336 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

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

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 356.74Molecular Weight (Monoisotopic): 356.0652AlogP: 3.50#Rotatable Bonds: 3
Polar Surface Area: 63.57Molecular Species: NEUTRALHBA: 4HBD: 1
#RO5 Violations: HBA (Lipinski): 5HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: 9.20CX Basic pKa: CX LogP: 3.26CX LogD: 3.26
Aromatic Rings: 3Heavy Atoms: 24QED Weighted: 0.78Np Likeness Score: -1.71

References

1. Wang H, Luo X, Ye M, Hou J, Robinson H, Ke H..  (2010)  Insight into binding of phosphodiesterase-9A selective inhibitors by crystal structures and mutagenesis.,  53  (4): [PMID:20121115] [10.1021/jm901519f]
2. PubChem BioAssay data set, 
3. Cheng ZB, Lu X, Bao JM, Han QH, Dong Z, Tang GH, Gan LS, Luo HB, Yin S..  (2014)  (±)-Torreyunlignans A-D, rare 8-9' linked neolignan enantiomers as phosphodiesterase-9A inhibitors from Torreya yunnanensis.,  77  (12): [PMID:25495612] [10.1021/np500528u]
4. Wu Y, Zhou Q, Zhang T, Li Z, Chen YP, Zhang P, Yu YF, Geng H, Tian YJ, Zhang C, Wang Y, Chen JW, Chen Y, Luo HB..  (2019)  Discovery of Potent, Selective, and Orally Bioavailable Inhibitors against Phosphodiesterase-9, a Novel Target for the Treatment of Vascular Dementia.,  62  (8): [PMID:30916555] [10.1021/acs.jmedchem.8b01041]
5. Sunke R, Bankala R, Thirupataiah B, Ramarao EVVS, Kumar JS, Doss HM, Medishetti R, Kulkarni P, Kapavarapu RK, Rasool M, Mudgal J, Mathew JE, Shenoy GG, Parsa KVL, Pal M..  (2019)  InCl3 mediated heteroarylation of indoles and their derivatization via CH activation strategy: Discovery of 2-(1H-indol-3-yl)-quinoxaline derivatives as a new class of PDE4B selective inhibitors for arthritis and/or multiple sclerosis.,  174  [PMID:31035240] [10.1016/j.ejmech.2019.04.020]
6. Jansen C, Kooistra AJ, Kanev GK, Leurs R, de Esch IJ, de Graaf C..  (2016)  PDEStrIAn: A Phosphodiesterase Structure and Ligand Interaction Annotated Database As a Tool for Structure-Based Drug Design.,  59  (15): [PMID:26908025] [10.1021/acs.jmedchem.5b01813]
7. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]
8. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]