4-[2-(4-Benzylpiperazin-1-yl)ethoxy]-2-(4'-propoxyphenyl)-quinoline

ID: ALA2385690

Chembl Id: CHEMBL2385690

PubChem CID: 71734204

Max Phase: Preclinical

Molecular Formula: C31H35N3O2

Molecular Weight: 481.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCOc1ccc(-c2cc(OCCN3CCN(Cc4ccccc4)CC3)c3ccccc3n2)cc1

Standard InChI:  InChI=1S/C31H35N3O2/c1-2-21-35-27-14-12-26(13-15-27)30-23-31(28-10-6-7-11-29(28)32-30)36-22-20-33-16-18-34(19-17-33)24-25-8-4-3-5-9-25/h3-15,23H,2,16-22,24H2,1H3

Standard InChI Key:  XOYWIWVXJJPLGN-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2385690

   4-[2-(4-Benzylpiperazin-1-yl)ethoxy]-2-(4-propoxyphenyl)quinoline

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: 481.64

Molecular Weight (Monoisotopic): 481.2729

AlogP: 5.89

#Rotatable Bonds: 10

Polar Surface Area: 37.83

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.87

CX LogP: 6.32

CX LogD: 5.72

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.28

Np Likeness Score: -1.07

References

1. Sabatini S, Gosetto F, Iraci N, Barreca ML, Massari S, Sancineto L, Manfroni G, Tabarrini O, Dimovska M, Kaatz GW, Cecchetti V..  (2013)  Re-evolution of the 2-phenylquinolines: ligand-based design, synthesis, and biological evaluation of a potent new class of Staphylococcus aureus NorA efflux pump inhibitors to combat antimicrobial resistance.,  56  (12): [PMID:23710549] [10.1021/jm400262a]

2. Nizi MG, Persoons L, Corona A, Felicetti T, Cernicchi G, Massari S, Manfroni G, Vangeel L, Barreca ML, Esposito F, Jochmans D, Milia J, Cecchetti V, Schols D, Neyts J, Tramontano E, Sabatini S, De Jonghe S, Tabarrini O..  (2022)  Discovery of 2-Phenylquinolines with Broad-Spectrum Anti-coronavirus Activity.,  13  (5.0): [PMID:35571875] [10.1021/acsmedchemlett.2c00123]

Source

Source(1):

• Scientific Literature