4-(4-chlorophenyl)-1-(4-(3,4-dichlorophenyl)-5-(isopropylthio)thiazol-2-yl)-3-methyl-1H-pyrazole-5-carboxylic acid

ID: ALA4228986

PubChem CID: 124119848

Max Phase: Preclinical

Molecular Formula: C23H18Cl3N3O2S2

Molecular Weight: 538.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nn(-c2nc(-c3ccc(Cl)c(Cl)c3)c(SC(C)C)s2)c(C(=O)O)c1-c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C23H18Cl3N3O2S2/c1-11(2)32-22-19(14-6-9-16(25)17(26)10-14)27-23(33-22)29-20(21(30)31)18(12(3)28-29)13-4-7-15(24)8-5-13/h4-11H,1-3H3,(H,30,31)

Standard InChI Key:  LTQHZDWRLACDRH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   27.0663  -10.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8835  -10.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1379  -10.2224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.4749   -9.7403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.8162  -10.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9177   -9.9676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5782  -10.4488    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   30.2400   -9.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9885   -9.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1713   -9.1908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.4689   -8.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2825   -8.6231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7635   -7.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4321   -7.2155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6150   -7.1312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1376   -7.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0389   -9.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5851  -11.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3631  -11.6608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0298  -12.4069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1759  -11.5763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5760   -8.0503    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   31.9124   -6.5543    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   31.0168  -10.2230    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.1856  -11.0226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9624  -11.2762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5776  -11.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7721  -11.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2911  -12.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6225  -12.9763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4395  -13.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9170  -12.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1421  -13.6374    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  1  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  6  2  0
  3  6  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  9 11  1  0
  5 17  1  0
  1 18  1  0
  2 19  1  0
 19 20  1  0
 19 21  2  0
 13 22  1  0
 14 23  1  0
  8 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 18 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 18  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4228986

   ---

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: 538.91

Molecular Weight (Monoisotopic): 536.9906

AlogP: 8.13

#Rotatable Bonds: 6

Polar Surface Area: 68.01

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.38

CX Basic pKa: 0.44

CX LogP: 7.96

CX LogD: 4.55

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.25

Np Likeness Score: -1.45

References

1. Cooper AB, Ciblat S, Shipps G, Levine J, Kostura M, Oza V, Constantineau-Forget L, Dery M, Grand-Maitre C, Bruneau-Latour N, Bellavance E, Patane M, Siddiqui A, Luther M..  (2017)  1-Thiazol-2-yl-N-3-methyl-1H-pyrozole-5-carboxylic acid derivatives as antitumor agents.,  27  (18): [PMID:28844391] [10.1016/j.bmcl.2017.08.003]

Source

Source(1):

• Scientific Literature