N4-(5-(2,5-dichlorophenylthio)-6-methoxyquinolin-8-yl)pentane-1,4-diamine

ID: ALA3245216

PubChem CID: 633200

Max Phase: Preclinical

Molecular Formula: C21H23Cl2N3OS

Molecular Weight: 436.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(NC(C)CCCN)c2ncccc2c1Sc1cc(Cl)ccc1Cl

Standard InChI:  InChI=1S/C21H23Cl2N3OS/c1-13(5-3-9-24)26-17-12-18(27-2)21(15-6-4-10-25-20(15)17)28-19-11-14(22)7-8-16(19)23/h4,6-8,10-13,26H,3,5,9,24H2,1-2H3

Standard InChI Key:  BCHIRTCLRJSMPT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    1.7319  -12.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7308  -13.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4456  -13.4572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4438  -11.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1592  -12.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1600  -13.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8753  -13.4511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5904  -13.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5856  -12.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8697  -11.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0174  -11.8046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0172  -10.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4475  -14.2822    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7340  -14.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7359  -15.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0186  -14.2855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4514  -15.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1648  -15.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8803  -15.9289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4414  -10.9791    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1546  -10.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8682  -10.9772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5810  -10.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5789   -9.7374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8582   -9.3272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1484   -9.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4310   -9.3362    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2965  -10.9740    0.0000 Cl  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
  1 11  1  0
 11 12  1  0
  3 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
  4 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 26 27  1  0
 23 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3245216

   8-[4-Amino-1-methylbutylamino]-5-[2,5-dichlorophenylthio]-6-methoxyquinoline

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: 436.41

Molecular Weight (Monoisotopic): 435.0939

AlogP: 6.24

#Rotatable Bonds: 8

Polar Surface Area: 60.17

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 10.20

CX LogP: 5.04

CX LogD: 2.44

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.44

Np Likeness Score: -0.76

References

1. Tanabe K, Chen EH, Verma BL, Saggiomo AJ, Nodiff EA..  (1978)  Modifications of primiaquine as antimalarials. 2. 5-Phenylthio and 5-anilino derivatives of primaquine.,  21  (1): [PMID:412967] [10.1021/jm00199a028]

Source

Source(1):

• Scientific Literature