4-((4-((3-(4-Ethylpiperazin-1-yl)propyl)amino)phenyl)amino)-6-fluoroquinoline-3-carbohydrazide

ID: ALA3628453

PubChem CID: 122193467

Max Phase: Preclinical

Molecular Formula: C25H32FN7O

Molecular Weight: 465.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1CCN(CCCNc2ccc(Nc3c(C(=O)NN)cnc4ccc(F)cc34)cc2)CC1

Standard InChI:  InChI=1S/C25H32FN7O/c1-2-32-12-14-33(15-13-32)11-3-10-28-19-5-7-20(8-6-19)30-24-21-16-18(26)4-9-23(21)29-17-22(24)25(34)31-27/h4-9,16-17,28H,2-3,10-15,27H2,1H3,(H,29,30)(H,31,34)

Standard InChI Key:  SEDAYQHCORRHEK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   -1.2964    1.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9122   -1.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9138   -2.4966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2109   -0.7445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2907   -2.9981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5870   -3.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5835   -5.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.4810   -6.0117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7815   -5.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0810   -6.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3815   -5.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2755   -7.5217    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2791   -6.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9819   -5.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6810   -6.0154    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6774   -7.5154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9746   -8.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2513   -1.3425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -15.5719   -8.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.5672   -9.4779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6321   -1.3486    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  1 10  1  0
  5 10  1  0
 11 12  2  0
 11 13  1  0
  3 11  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
 23 24  1  0
 21 22  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 25 30  1  0
 24 28  1  0
 18 21  1  0
 14 15  1  0
  4 14  1  0
 13 31  1  0
 25 32  1  0
 32 33  1  0
  7 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3628453

   ---

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: 465.58

Molecular Weight (Monoisotopic): 465.2652

AlogP: 3.16

#Rotatable Bonds: 9

Polar Surface Area: 98.55

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.81

CX Basic pKa: 8.40

CX LogP: 3.32

CX LogD: 2.28

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.17

Np Likeness Score: -1.71

References

1. Medapi B, Suryadevara P, Renuka J, Sridevi JP, Yogeeswari P, Sriram D..  (2015)  4-Aminoquinoline derivatives as novel Mycobacterium tuberculosis GyrB inhibitors: Structural optimization, synthesis and biological evaluation.,  103  [PMID:26318054] [10.1016/j.ejmech.2015.06.032]

Source

Source(1):

• Scientific Literature