(+/-)-N-{(4-Chlorophenyl)[4-(pyrrolidin-1-ylmethyl)phenyl]methyl}-7-chloro-4-aminoquinoline

ID: ALA498010

Chembl Id: CHEMBL498010

PubChem CID: 25004137

Max Phase: Preclinical

Molecular Formula: C27H25Cl2N3

Molecular Weight: 462.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Clc1ccc(C(Nc2ccnc3cc(Cl)ccc23)c2ccc(CN3CCCC3)cc2)cc1

Standard InChI:  InChI=1S/C27H25Cl2N3/c28-22-9-7-21(8-10-22)27(20-5-3-19(4-6-20)18-32-15-1-2-16-32)31-25-13-14-30-26-17-23(29)11-12-24(25)26/h3-14,17,27H,1-2,15-16,18H2,(H,30,31)

Standard InChI Key:  SHXACPDVVQQBFH-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA498010

   7-chloro-N-[(4-chlorophenyl)-[4-(pyrrolidin-1-ylmethyl)phenyl]methyl]quinolin-4-amine

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: 462.42

Molecular Weight (Monoisotopic): 461.1426

AlogP: 7.34

#Rotatable Bonds: 6

Polar Surface Area: 28.16

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.28

CX LogP: 6.67

CX LogD: 4.59

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.33

Np Likeness Score: -1.23

References

1. Gemma S, Campiani G, Butini S, Joshi BP, Kukreja G, Coccone SS, Bernetti M, Persico M, Nacci V, Fiorini I, Novellino E, Taramelli D, Basilico N, Parapini S, Yardley V, Croft S, Keller-Maerki S, Rottmann M, Brun R, Coletta M, Marini S, Guiso G, Caccia S, Fattorusso C..  (2009)  Combining 4-aminoquinoline- and clotrimazole-based pharmacophores toward innovative and potent hybrid antimalarials.,  52  (2): [PMID:19113955] [10.1021/jm801352s]

2. Gemma S, Camodeca C, Sanna Coccone S, Joshi BP, Bernetti M, Moretti V, Brogi S, Bonache de Marcos MC, Savini L, Taramelli D, Basilico N, Parapini S, Rottmann M, Brun R, Lamponi S, Caccia S, Guiso G, Summers RL, Martin RE, Saponara S, Gorelli B, Novellino E, Campiani G, Butini S..  (2012)  Optimization of 4-aminoquinoline/clotrimazole-based hybrid antimalarials: further structure-activity relationships, in vivo studies, and preliminary toxicity profiling.,  55  (15): [PMID:22783984] [10.1021/jm300802s]

Source

Source(1):

• Scientific Literature