8-chloro-4-[(3-chloro-4-fluorophenyl)amino]-6-{[(1-oxidopyridin-2-yl)methyl]amino}quinoline-3-carbonitrile

ID: ALA395573

Chembl Id: CHEMBL395573

PubChem CID: 17759787

Max Phase: Preclinical

Molecular Formula: C22H14Cl2FN5O

Molecular Weight: 454.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1cnc2c(Cl)cc(NCc3cccc[n+]3[O-])cc2c1Nc1ccc(F)c(Cl)c1

Standard InChI:  InChI=1S/C22H14Cl2FN5O/c23-18-8-14(4-5-20(18)25)29-21-13(10-26)11-28-22-17(21)7-15(9-19(22)24)27-12-16-3-1-2-6-30(16)31/h1-9,11,27H,12H2,(H,28,29)

Standard InChI Key:  ORVPEVIDEJOHIY-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA395573

   2-[({8-Chloro-4-[(3-chloro-4-fluorophenyl)amino]-3-cyanoquinolin-6-yl}amino)methyl]-1-oxidopyridin-1-ium

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: 454.29

Molecular Weight (Monoisotopic): 453.0559

AlogP: 5.54

#Rotatable Bonds: 5

Polar Surface Area: 87.68

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 2.67

CX LogP: 3.63

CX LogD: 3.63

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.31

Np Likeness Score: -1.67

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]

Source

Source(1):

• Scientific Literature