3-(5-((2-(benzo[d]thiazol-2-yl)hydrazono)methyl)furan-2-yl)-2-methylbenzoic acid

ID: ALA2398290

Max Phase: Preclinical

Molecular Formula: C20H15N3O3S

Molecular Weight: 377.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(C(=O)O)cccc1-c1ccc(/C=N/Nc2nc3ccccc3s2)o1

Standard InChI:  InChI=1S/C20H15N3O3S/c1-12-14(5-4-6-15(12)19(24)25)17-10-9-13(26-17)11-21-23-20-22-16-7-2-3-8-18(16)27-20/h2-11H,1H3,(H,22,23)(H,24,25)/b21-11+

Standard InChI Key:  WRYUQDYTDHZOQS-SRZZPIQSSA-N

Molfile:  

     RDKit          2D

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   -7.1169  -11.7732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4134  -12.1821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4117  -10.5448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7005  -10.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6971  -11.7732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9131  -12.0230    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4356  -11.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9218  -10.6911    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6184  -11.3494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2139  -10.6392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3967  -10.6344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9921   -9.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1830   -9.8318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0180   -9.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7276   -8.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3289   -9.1775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2736   -8.6944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3929   -9.1726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1369   -8.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2180   -8.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5491   -7.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1957   -7.8844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8006   -9.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7196  -10.1263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5453   -8.9767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114   -9.9857    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  1  0
  8  9  2  0
  9  5  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 13  2  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 15 18  1  0
 20 24  1  0
 24 25  2  0
 24 26  1  0
 19 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2398290

   ---

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: 377.43

Molecular Weight (Monoisotopic): 377.0834

AlogP: 5.01

#Rotatable Bonds: 5

Polar Surface Area: 87.72

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.96

CX Basic pKa: 3.22

CX LogP: 4.95

CX LogD: 2.17

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.38

Np Likeness Score: -1.82

References

1. Sleebs BE, Kersten WJ, Kulasegaram S, Nikolakopoulos G, Hatzis E, Moss RM, Parisot JP, Yang H, Czabotar PE, Fairlie WD, Lee EF, Adams JM, Chen L, van Delft MF, Lowes KN, Wei A, Huang DC, Colman PM, Street IP, Baell JB, Watson K, Lessene G..  (2013)  Discovery of potent and selective benzothiazole hydrazone inhibitors of Bcl-XL.,  56  (13): [PMID:23767404] [10.1021/jm400556w]

2. Hennessy EJ..  (2016)  Selective inhibitors of Bcl-2 and Bcl-xL: Balancing antitumor activity with on-target toxicity.,  26  (9): [PMID:26988306] [10.1016/j.bmcl.2016.03.032]

Source

Source(1):

• Scientific Literature