(+/-)-N-{(3-Chlorophenyl)[4-(pyrrolidin-1-ylmethyl)phenyl]methyl}-7-chloro-4-aminoquinoline

ID: ALA524065

Chembl Id: CHEMBL524065

Cas Number: 1050526-88-9

PubChem CID: 25004141

Max Phase: Preclinical

Molecular Formula: C27H25Cl2N3

Molecular Weight: 462.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Clc1cccc(C(Nc2ccnc3cc(Cl)ccc23)c2ccc(CN3CCCC3)cc2)c1

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

Standard InChI Key:  UBHRCFWJZMCKSC-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA524065

   4-Quinolinamine,7-chloro-N-[(3-chlorophenyl)[4-(1-pyrrolidinylmethyl)phenyl]methyl]-

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: -1.40

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. Kaur K, Jain M, Reddy RP, Jain R..  (2010)  Quinolines and structurally related heterocycles as antimalarials.,  45  (8): [PMID:20466465] [10.1016/j.ejmech.2010.04.011]

3. 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]

4. Peterková L, Kmoníčková E, Ruml T, Rimpelová S..  (2020)  Sarco/Endoplasmic Reticulum Calcium ATPase Inhibitors: Beyond Anticancer Perspective.,  63  (5): [PMID:32030976] [10.1021/acs.jmedchem.9b01509]

Source

Source(1):

• Scientific Literature