4-Methyl-7-[3-((methylamino)methyl)phenethyl]quinolin-2-amine Dihydrochloride

ID: ALA4074659

PubChem CID: 124136846

Max Phase: Preclinical

Molecular Formula: C20H25Cl2N3

Molecular Weight: 305.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNCc1cccc(CCc2ccc3c(C)cc(N)nc3c2)c1.Cl.Cl

Standard InChI:  InChI=1S/C20H23N3.2ClH/c1-14-10-20(21)23-19-12-16(8-9-18(14)19)7-6-15-4-3-5-17(11-15)13-22-2;;/h3-5,8-12,22H,6-7,13H2,1-2H3,(H2,21,23);2*1H

Standard InChI Key:  OZIBQKYYCZDPRI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 25  0  0  0  0  0  0  0  0999 V2000
   12.3750  -17.1187    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.7129  -18.9994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9980  -18.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9980  -17.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7129  -17.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4236  -17.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1385  -17.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8534  -17.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8534  -18.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1385  -18.9994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4236  -18.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2831  -18.9994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5683  -18.9994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2790  -18.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9938  -18.9994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7046  -18.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4195  -18.9994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4195  -19.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7046  -20.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9938  -19.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1344  -18.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8450  -18.9994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5599  -18.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7129  -16.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1964  -17.0893    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  2 11  1  0
  6 11  1  0
  3 12  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 15 20  2  0
 22 23  1  0
 21 22  1  0
 17 21  1  0
  9 13  1  0
  5 24  1  0
M  END

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: 305.43

Molecular Weight (Monoisotopic): 305.1892

AlogP: 3.63

#Rotatable Bonds: 5

Polar Surface Area: 50.94

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.43

CX LogP: 4.50

CX LogD: 2.27

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.76

Np Likeness Score: -0.15

References

1. Cinelli MA, Li H, Chreifi G, Poulos TL, Silverman RB..  (2017)  Nitrile in the Hole: Discovery of a Small Auxiliary Pocket in Neuronal Nitric Oxide Synthase Leading to the Development of Potent and Selective 2-Aminoquinoline Inhibitors.,  60  (9): [PMID:28422508] [10.1021/acs.jmedchem.7b00259]

2. Vasu D, Reidl CT, Wang E, Yang S, Silverman RB..  (2023)  Improved synthesis and anticancer activity of a potent neuronal nitric oxide synthase inhibitor.,  90  [PMID:37196870] [10.1016/j.bmcl.2023.129329]

Source

Source(1):

• Scientific Literature