5,5'-(4-(Trifluoromethyl)benzylazanediyl)bis(methylene)diquinolin-8-ol

ID: ALA478507

Chembl Id: CHEMBL478507

Cas Number: 1146365-12-9

PubChem CID: 25268906

Max Phase: Preclinical

Molecular Formula: C28H22F3N3O2

Molecular Weight: 489.50

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: JLK-1486 | UNII-8KG95Q2DQH|JLK-1486|8KG95Q2DQH|JLK1486|1146365-12-9|5,5-(4-(Trifluromethyl)benzylazanediyl)bis(methylene)diquinolin-8-ol|5,5'-((((4-(Trifluoromethyl)phenyl)methyl)imino)bis(methylene))bis(8-quinolinol)|8-Quinolinol, 5,5'-((((4-(trifluoromethyl)phenyl)methyl)imino)bis(methylene))bis-|5-(((8-Hydroxyquinolin-5-yl)methyl-((4-(trifluoromethyl)phenyl)methyl)amino)methyl)quinolin-8-ol|5-[[(8-hydroxyquinolin-5-yl)methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]methyl]quinolin-8-ol|CHEMBLShow More

Canonical SMILES:  Oc1ccc(CN(Cc2ccc(C(F)(F)F)cc2)Cc2ccc(O)c3ncccc23)c2cccnc12

Standard InChI:  InChI=1S/C28H22F3N3O2/c29-28(30,31)21-9-5-18(6-10-21)15-34(16-19-7-11-24(35)26-22(19)3-1-13-32-26)17-20-8-12-25(36)27-23(20)4-2-14-33-27/h1-14,35-36H,15-17H2

Standard InChI Key:  JZARXLRJMQKPON-UHFFFAOYSA-N

Alternative Forms

  1. Parent:

Associated Targets(Human)

HCT-116 (91556 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCT-15 (51914 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-OV-3 (52876 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PC-3 (62116 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SF-268 (49410 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HL-60 (67320 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
K562 (73714 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HepG2 (196354 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BXPC-3 (2997 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LoVo (4724 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
T98G (1524 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCB1 Tchem P-glycoprotein 1 (14716 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

HT-22 (3261 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Blood brain barrier (2 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Brain (4256 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cerebrospinal fluid (288 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: 489.50Molecular Weight (Monoisotopic): 489.1664AlogP: 6.42#Rotatable Bonds: 6
Polar Surface Area: 69.48Molecular Species: BASEHBA: 5HBD: 2
#RO5 Violations: 1HBA (Lipinski): 5HBD (Lipinski): 2#RO5 Violations (Lipinski): 1
CX Acidic pKa: 8.19CX Basic pKa: 9.50CX LogP: 4.94CX LogD: 4.52
Aromatic Rings: 5Heavy Atoms: 36QED Weighted: 0.29Np Likeness Score: -0.74

References

1. Moret V, Laras Y, Cresteil T, Aubert G, Ping DQ, Di C, Barthélémy-Requin M, Béclin C, Peyrot V, Allegro D, Rolland A, De Angelis F, Gatti E, Pierre P, Pasquini L, Petrucci E, Testa U, Kraus JL..  (2009)  Discovery of a new family of bis-8-hydroxyquinoline substituted benzylamines with pro-apoptotic activity in cancer cells: synthesis, structure-activity relationship, and action mechanism studies.,  44  (2): [PMID:18485536] [10.1016/j.ejmech.2008.03.042]
2. Madonna S, Béclin C, Laras Y, Moret V, Marcowycz A, Lamoral-Theys D, Dubois J, Barthelemy-Requin M, Lenglet G, Depauw S, Cresteil T, Aubert G, Monnier V, Kiss R, David-Cordonnier MH, Kraus JL..  (2010)  Structure-activity relationships and mechanism of action of antitumor bis 8-hydroxyquinoline substituted benzylamines.,  45  (2): [PMID:19931949] [10.1016/j.ejmech.2009.11.006]
3. Madonna S, Maher P, Kraus JL..  (2010)  N,N-Bis-(8-hydroxyquinoline-5-yl methyl)-benzyl substituted amines (HQNBA): peroxisome proliferator-activated receptor (PPAR-γ) agonists with neuroprotective properties.,  20  (23): [PMID:20971007] [10.1016/j.bmcl.2010.09.134]
4. Barthelemy-Requin M, Nugier J, Madonna S, Kraus J.  (2012)  Bloodbrain barrier permeability and transport studies of JLK1486: a new antiglioblastoma drug,  21  (7): [10.1007/s00044-011-9649-6]

Source