3-(4-Acetylpiperazin-1-yl)-5-(3-nitrobenzylamino)-7-(trifluoromethyl)quinoline

ID: ALA1766529

Chembl Id: CHEMBL1766529

PubChem CID: 50997096

Max Phase: Preclinical

Molecular Formula: C23H22F3N5O3

Molecular Weight: 473.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N1CCN(c2cnc3cc(C(F)(F)F)cc(NCc4cccc([N+](=O)[O-])c4)c3c2)CC1

Standard InChI:  InChI=1S/C23H22F3N5O3/c1-15(32)29-5-7-30(8-6-29)19-12-20-21(10-17(23(24,25)26)11-22(20)28-14-19)27-13-16-3-2-4-18(9-16)31(33)34/h2-4,9-12,14,27H,5-8,13H2,1H3

Standard InChI Key:  DORMVCLDXDMKMM-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1766529

   3-(4-Acetylpiperazin-1-yl)-5-(3-nitrobenzylamino)-7-(trifluoromethyl)quinoline

2. Alternative Forms:

   

   ALA1766529

   1-[4-[5-[[Deuterio-(3-nitrophenyl)methyl]amino]-7-(trifluoromethyl)quinolin-3-yl]piperazin-1-yl]ethanone

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: 473.46

Molecular Weight (Monoisotopic): 473.1675

AlogP: 4.44

#Rotatable Bonds: 5

Polar Surface Area: 91.61

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.55

CX LogP: 3.33

CX LogD: 3.33

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.44

Np Likeness Score: -1.91

References

1. Wang Y, Ai J, Wang Y, Chen Y, Wang L, Liu G, Geng M, Zhang A..  (2011)  Synthesis and c-Met kinase inhibition of 3,5-disubstituted and 3,5,7-trisubstituted quinolines: identification of 3-(4-acetylpiperazin-1-yl)-5-(3-nitrobenzylamino)-7- (trifluoromethyl)quinoline as a novel anticancer agent.,  54  (7): [PMID:21405128] [10.1021/jm101340q]

2. Wang Y, Ai J, Yue J, Peng X, Ji Y, Zhao A, Gao X, Wang Y, Chen Y, Liu G, Gao Z, Geng M, Zhang A.  (2012)  Further SAR studies on 3,5-diamino-7-trifluoromethylquinolines as highly potent tyrosine kinase c-Met inhibitors: efforts to correct hERG inhibition,  3  (11): [10.1039/C2MD20192E]

Source

Source(1):

• Scientific Literature