N1-(benzo[b]thiophen-3-ylmethyl)-N3-(7-chloroquinolin-4-yl)propane-1,3-diamine

ID: ALA4211180

PubChem CID: 145967384

Max Phase: Preclinical

Molecular Formula: C21H20ClN3S

Molecular Weight: 381.93

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Clc1ccc2c(NCCCNCc3csc4ccccc34)ccnc2c1

Standard InChI:  InChI=1S/C21H20ClN3S/c22-16-6-7-18-19(8-11-25-20(18)12-16)24-10-3-9-23-13-15-14-26-21-5-2-1-4-17(15)21/h1-2,4-8,11-12,14,23H,3,9-10,13H2,(H,24,25)

Standard InChI Key:  VMHIFTBHFFDLSB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    3.8958  -16.9161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6096  -16.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6068  -15.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8940  -15.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1837  -16.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1859  -15.6852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4759  -15.2720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7631  -15.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7647  -16.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4754  -16.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8905  -14.4491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6006  -14.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3142  -14.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0202  -14.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7337  -14.4370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4438  -14.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1574  -14.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2484  -15.2449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0526  -15.4114    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.9087  -14.0930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4598  -14.7008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2582  -14.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5066  -13.7446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9506  -13.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1542  -13.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0539  -16.9190    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  5  2  0
  4 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 21  1  0
 20 17  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
  9 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4211180

   ---

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: 381.93

Molecular Weight (Monoisotopic): 381.1066

AlogP: 5.69

#Rotatable Bonds: 7

Polar Surface Area: 36.95

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.34

CX LogP: 4.50

CX LogD: 2.34

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.40

Np Likeness Score: -1.61

References

1. Konstantinović J, Videnović M, Orsini S, Bogojević K, D'Alessandro S, Scaccabarozzi D, Terzić Jovanović N, Gradoni L, Basilico N, Šolaja BA..  (2018)  Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania infantum Infected Mice.,  9  (7): [PMID:30034591] [10.1021/acsmedchemlett.8b00053]

Source

Source(1):

• Scientific Literature