8-bromo-4-[(3-chloro-4-fluorophenyl)amino]-6-{[(1-methyl-1H-imidazol-4-yl)methyl]amino}quinoline-3-carbonitrile

ID: ALA230761

Chembl Id: CHEMBL230761

PubChem CID: 17758574

Max Phase: Preclinical

Molecular Formula: C21H15BrClFN6

Molecular Weight: 485.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1cnc(CNc2cc(Br)c3ncc(C#N)c(Nc4ccc(F)c(Cl)c4)c3c2)c1

Standard InChI:  InChI=1S/C21H15BrClFN6/c1-30-10-15(28-11-30)9-26-14-4-16-20(29-13-2-3-19(24)18(23)6-13)12(7-25)8-27-21(16)17(22)5-14/h2-6,8,10-11,26H,9H2,1H3,(H,27,29)

Standard InChI Key:  GTXFFNURYUQKEA-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA230761

   8-bromo-4-(3-chloro-4-fluorophenylamino)-6-((1-methyl-1H-imidazol-4-yl)methylamino)quinoline-3-carbonitrile

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 485.75

Molecular Weight (Monoisotopic): 484.0214

AlogP: 5.75

#Rotatable Bonds: 5

Polar Surface Area: 78.56

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 5.86

CX LogP: 4.33

CX LogD: 4.31

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.38

Np Likeness Score: -1.81

References

1. Green N, Hu Y, Janz K, Li HQ, Kaila N, Guler S, Thomason J, Joseph-McCarthy D, Tam SY, Hotchandani R, Wu J, Huang A, Wang Q, Leung L, Pelker J, Marusic S, Hsu S, Telliez JB, Hall JP, Cuozzo JW, Lin LL..  (2007)  Inhibitors of tumor progression loci-2 (Tpl2) kinase and tumor necrosis factor alpha (TNF-alpha) production: selectivity and in vivo antiinflammatory activity of novel 8-substituted-4-anilino-6-aminoquinoline-3-carbonitriles.,  50  (19): [PMID:17715908] [10.1021/jm070436q]

2. Wu J, Green N, Hotchandani R, Hu Y, Condon J, Huang A, Kaila N, Li HQ, Guler S, Li W, Tam SY, Wang Q, Pelker J, Marusic S, Hsu S, Perry Hall J, Telliez JB, Cui J, Lin LL..  (2009)  Selective inhibitors of tumor progression loci-2 (Tpl2) kinase with potent inhibition of TNF-alpha production in human whole blood.,  19  (13): [PMID:19464884] [10.1016/j.bmcl.2009.05.009]

Source

Source(1):

• Scientific Literature