2-benzyl-N4-(3-bromophenyl)-1H-indole-4,6-diamine

ID: ALA499344

Chembl Id: CHEMBL499344

PubChem CID: 3008958

Max Phase: Preclinical

Molecular Formula: C19H16BrN5

Molecular Weight: 394.28

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  Nc1nc(Nc2cccc(Br)c2)c2cc(Cc3ccccc3)[nH]c2n1

Standard InChI:  InChI=1S/C19H16BrN5/c20-13-7-4-8-14(10-13)22-17-16-11-15(9-12-5-2-1-3-6-12)23-18(16)25-19(21)24-17/h1-8,10-11H,9H2,(H4,21,22,23,24,25)

Standard InChI Key:  ZCULMARKDXJUJE-UHFFFAOYSA-N

Alternative Forms

Associated Targets(Human)

EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FLT1 Tclin Vascular endothelial growth factor receptor 1 (6262 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PDGFRB Tclin Platelet-derived growth factor receptor beta (5195 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A-431 (6446 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Gallus gallus (1187 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Igf1r Insulin-like growth factor 1 receptor (35 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Insr Insulin receptor (70 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: 394.28Molecular Weight (Monoisotopic): 393.0589AlogP: 4.64#Rotatable Bonds: 4
Polar Surface Area: 79.62Molecular Species: NEUTRALHBA: 4HBD: 3
#RO5 Violations: HBA (Lipinski): 5HBD (Lipinski): 4#RO5 Violations (Lipinski):
CX Acidic pKa: 13.16CX Basic pKa: 7.60CX LogP: 5.02CX LogD: 4.62
Aromatic Rings: 4Heavy Atoms: 25QED Weighted: 0.47Np Likeness Score: -0.90

References

1. Gangjee A, Namjoshi OA, Yu J, Ihnat MA, Thorpe JE, Warnke LA..  (2008)  Design, synthesis and biological evaluation of substituted pyrrolo[2,3-d]pyrimidines as multiple receptor tyrosine kinase inhibitors and antiangiogenic agents.,  16  (10): [PMID:18467105] [10.1016/j.bmc.2008.04.019]
2. Li R, Pourpak A, Morris SW..  (2009)  Inhibition of the insulin-like growth factor-1 receptor (IGF1R) tyrosine kinase as a novel cancer therapy approach.,  52  (16): [PMID:19610618] [10.1021/jm9002395]
3. Gangjee A, Zhao Y, Raghavan S, Ihnat MA, Disch BC..  (2010)  Design, synthesis and evaluation of 2-amino-4-m-bromoanilino-6-arylmethyl-7H-pyrrolo[2,3-d]pyrimidines as tyrosine kinase inhibitors and antiangiogenic agents.,  18  (14): [PMID:20558072] [10.1016/j.bmc.2010.05.049]
4. Gangjee A, Zaware N, Raghavan S, Yang J, Thorpe JE, Ihnat MA..  (2012)  N⁴-(3-Bromophenyl)-7-(substituted benzyl) pyrrolo[2,3-d]pyrimidines as potent multiple receptor tyrosine kinase inhibitors: design, synthesis, and in vivo evaluation.,  20  (7): [PMID:22370340] [10.1016/j.bmc.2012.01.029]

Source