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

ID: ALA220037

Chembl Id: CHEMBL220037

PubChem CID: 16066845

Max Phase: Preclinical

Molecular Formula: C20H14ClFN6

Molecular Weight: 392.82

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1cnc2ccc(NCc3c[nH]cn3)cc2c1Nc1ccc(F)c(Cl)c1

Standard InChI:  InChI=1S/C20H14ClFN6/c21-17-6-14(1-3-18(17)22)28-20-12(7-23)8-26-19-4-2-13(5-16(19)20)25-10-15-9-24-11-27-15/h1-6,8-9,11,25H,10H2,(H,24,27)(H,26,28)

Standard InChI Key:  HFOOHVUKODGHBP-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA220037

   4-[(3-chloro-4-fluorophenyl)amino]-6-[(1H-imidazol-4-ylmethyl)amino]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: 392.82

Molecular Weight (Monoisotopic): 392.0953

AlogP: 4.98

#Rotatable Bonds: 5

Polar Surface Area: 89.42

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.91

CX Basic pKa: 6.26

CX LogP: 3.33

CX LogD: 3.31

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.45

Np Likeness Score: -1.85

References

1. Hu Y, Green N, Gavrin LK, Janz K, Kaila N, Li HQ, Thomason JR, Cuozzo JW, Hall JP, Hsu S, Nickerson-Nutter C, Telliez JB, Lin LL, Tam S..  (2006)  Inhibition of Tpl2 kinase and TNFalpha production with quinoline-3-carbonitriles for the treatment of rheumatoid arthritis.,  16  (23): [PMID:16973359] [10.1016/j.bmcl.2006.08.102]

2. 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]

3. Kaila N, Green N, Li HQ, Hu Y, Janz K, Gavrin LK, Thomason J, Tam S, Powell D, Cuozzo J, Hall JP, Telliez JB, Hsu S, Nickerson-Nutter C, Wang Q, Lin LL..  (2007)  Identification of a novel class of selective Tpl2 kinase inhibitors: 4-Alkylamino-[1,7]naphthyridine-3-carbonitriles.,  15  (19): [PMID:17664070] [10.1016/j.bmc.2007.06.054]

4. 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]

5. Ibrahim DA, Abou El Ella DA, El-Motwally AM, Aly RM..  (2015)  Molecular design and synthesis of certain new quinoline derivatives having potential anticancer activity.,  102  [PMID:26256032] [10.1016/j.ejmech.2015.07.030]

Source

Source(1):

• Scientific Literature