2-quinolinecarboxaldehyde 4-(1-benzylpiperidin-4-yl)thiosemicarbazone

ID: ALA4168083

PubChem CID: 145420208

Max Phase: Preclinical

Molecular Formula: C23H25N5S

Molecular Weight: 403.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  S=C(N/N=C/c1ccc2ccccc2n1)NC1CCN(Cc2ccccc2)CC1

Standard InChI:  InChI=1S/C23H25N5S/c29-23(27-24-16-21-11-10-19-8-4-5-9-22(19)25-21)26-20-12-14-28(15-13-20)17-18-6-2-1-3-7-18/h1-11,16,20H,12-15,17H2,(H2,26,27,29)/b24-16+

Standard InChI Key:  ZLUQWYLLFBQNGQ-LFVJCYFKSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   11.6181   -3.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6170   -4.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3317   -4.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0481   -4.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0452   -3.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3298   -2.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9022   -4.4721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1882   -4.0591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1927   -3.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4828   -2.8171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7657   -3.2254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7631   -4.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4776   -4.4688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0532   -2.8097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3369   -3.2189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6245   -2.8031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3332   -4.0438    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9082   -3.2123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1957   -2.7967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4794   -3.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7695   -2.7876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0537   -3.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4798   -4.0266    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7669   -4.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0535   -4.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3386   -4.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3361   -5.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0543   -5.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7661   -5.2588    0.0000 C   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  1  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 25  2  0
 24 23  2  0
 23 20  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4168083

   ---

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: 403.56

Molecular Weight (Monoisotopic): 403.1831

AlogP: 3.70

#Rotatable Bonds: 5

Polar Surface Area: 52.55

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.29

CX Basic pKa: 8.41

CX LogP: 4.47

CX LogD: 3.42

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.39

Np Likeness Score: -1.73

References

1. Palanimuthu D, Poon R, Sahni S, Anjum R, Hibbs D, Lin HY, Bernhardt PV, Kalinowski DS, Richardson DR..  (2017)  A novel class of thiosemicarbazones show multi-functional activity for the treatment of Alzheimer's disease.,  139  [PMID:28841514] [10.1016/j.ejmech.2017.08.021]

Source

Source(1):

• Scientific Literature