ID: ALA423288

Max Phase: Preclinical

Molecular Formula: C18H17N5O

Molecular Weight: 319.37

Molecule Type: Small molecule

Associated Items:

Representations

Canonical SMILES:  CC(=O)Nc1ccc(C)c(Nc2nccc(-c3cccnc3)n2)c1

Standard InChI:  InChI=1S/C18H17N5O/c1-12-5-6-15(21-13(2)24)10-17(12)23-18-20-9-7-16(22-18)14-4-3-8-19-11-14/h3-11H,1-2H3,(H,21,24)(H,20,22,23)

Standard InChI Key:  PMGVYOWQUQXHSP-UHFFFAOYSA-N

Associated Targets(Human)

Platelet-derived growth factor receptor 507 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Epidermal growth factor receptor erbB1 33727 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Tyrosine-protein kinase SRC 10310 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Protein kinase C alpha 5923 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Protein kinase C delta 2953 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

cAMP-dependent protein kinase (PKA) 929 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Tyrosine-protein kinase ABL 18331 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Bcr/Abl fusion protein 1667 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Platelet-derived growth factor receptor 285 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

Properties

Molecular Weight: 319.37Molecular Weight (Monoisotopic): 319.1433AlogP: 3.55#Rotatable Bonds: 4
Polar Surface Area: 79.80Molecular Species: NEUTRALHBA: 5HBD: 2
#RO5 Violations: 0HBA (Lipinski): 6HBD (Lipinski): 2#RO5 Violations (Lipinski): 0
CX Acidic pKa: 12.69CX Basic pKa: 4.26CX LogP: 2.73CX LogD: 2.73
Aromatic Rings: 3Heavy Atoms: 24QED Weighted: 0.77Np Likeness Score: -1.83

References

1. Zimmermann J, Buchdunger E, Mett H, Meyer T, Lydon NB, Traxler P.  (1996)  Phenylamino-pyrimidine (PAP) derivatives: a new class of potent and highly selective PDGF-receptor autophosphorylation inhibitors,  (11): [10.1016/0960-894X(96)00197-7]
2. Zimmermann J, Buchdunger E, Mett H, Meyer T, Lydon NB.  (1997)  Potent and selective inhibitors of the Abl-kinase: phenylamino-pyrimidine (PAP) derivatives,  (2): [10.1016/S0960-894X(96)00601-4]
3. 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]
4. Cui J, Fu R, Zhou LH, Chen SP, Li GW, Qian SX, Liu S..  (2013)  BCR-ABL tyrosine kinase inhibitor pharmacophore model derived from a series of phenylaminopyrimidine-based (PAP) derivatives.,  23  (8): [PMID:23473682] [10.1016/j.bmcl.2013.01.113]
5. Sun W,Netzer WJ,Sinha A,Gindinova K,Chang E,Sinha SC.  (2019)  Development of Gleevec Analogues for Reducing Production of β-Amyloid Peptides through Shifting β-Cleavage of Amyloid Precursor Proteins.,  62  (6): [PMID:30873837] [10.1021/acs.jmedchem.8b02007]

Source