7-chloro-N-(4-(6-methoxyquinolin-8-ylamino)pentyl)quinolin-4-amine

ID: ALA3219153

PubChem CID: 56949516

Max Phase: Preclinical

Molecular Formula: C24H25ClN4O

Molecular Weight: 420.94

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(NC(C)CCCNc2ccnc3cc(Cl)ccc23)c2ncccc2c1

Standard InChI:  InChI=1S/C24H25ClN4O/c1-16(29-23-15-19(30-2)13-17-6-4-11-28-24(17)23)5-3-10-26-21-9-12-27-22-14-18(25)7-8-20(21)22/h4,6-9,11-16,29H,3,5,10H2,1-2H3,(H,26,27)

Standard InChI Key:  XGGLHZNSHPBQNK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    3.0279   -5.1878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0267   -6.0152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7416   -6.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7398   -4.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4552   -5.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4560   -6.0111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1714   -6.4220    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8865   -6.0072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8816   -5.1772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1657   -4.7699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3119   -6.4271    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.1614   -3.9449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8736   -3.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5904   -3.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3027   -3.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0194   -3.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7317   -3.5135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0237   -4.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4484   -3.9222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8772   -4.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8701   -3.9102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1537   -3.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1638   -5.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4505   -4.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7433   -5.1627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7482   -5.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4663   -6.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1705   -5.9728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5809   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5736   -2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  2 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 17 19  1  0
 19 24  2  0
 23 20  2  0
 20 21  1  0
 21 22  2  0
 22 19  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 21 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3219153

   N1-(7-chloro-4-quinolyl)-N4-(6-methoxy-8-quinolyl)pentane-1,4-diamine

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: 420.94

Molecular Weight (Monoisotopic): 420.1717

AlogP: 6.14

#Rotatable Bonds: 8

Polar Surface Area: 59.07

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.31

CX LogP: 4.48

CX LogD: 4.23

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.34

Np Likeness Score: -0.96

References

1. Pal C, Sarkar S, Mazumder S, Adhikari S, Bandyopadhyay U.  (2013)  Synthesis and biological evaluation of primaquinechloroquine twin drug: a novel heme-interacting molecule prevents free heme and hydroxyl radical-mediated protein degradation,  4  (4): [10.1039/C3MD00019B]

2. Mushtaque M, Shahjahan..  (2015)  Reemergence of chloroquine (CQ) analogs as multi-targeting antimalarial agents: a review.,  90  [PMID:25461328] [10.1016/j.ejmech.2014.11.022]

3. Oliveira R, Miranda D, Magalhães J, Capela R, Perry MJ, O'Neill PM, Moreira R, Lopes F..  (2015)  From hybrid compounds to targeted drug delivery in antimalarial therapy.,  23  (16): [PMID:25913864] [10.1016/j.bmc.2015.04.017]

4. Vandekerckhove S, D'hooghe M..  (2015)  Quinoline-based antimalarial hybrid compounds.,  23  (16): [PMID:25593097] [10.1016/j.bmc.2014.12.018]

Source

Source(1):

• Scientific Literature