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

ID: ALA4229096

PubChem CID: 145988418

Max Phase: Preclinical

Molecular Formula: C22H18Cl2N4O2S2

Molecular Weight: 505.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(-c2cc(Cl)cc(Cl)c2)c(C(=O)O)nn1-c1nc(-c2cccnc2)c(SC(C)C)s1

Standard InChI:  InChI=1S/C22H18Cl2N4O2S2/c1-11(2)31-21-18(13-5-4-6-25-10-13)26-22(32-21)28-12(3)17(19(27-28)20(29)30)14-7-15(23)9-16(24)8-14/h4-11H,1-3H3,(H,29,30)

Standard InChI Key:  BRXSLZUMZPHQNM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   25.9231   -5.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7403   -5.0105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9947   -4.2338    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.3317   -3.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6729   -4.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7718   -3.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4323   -4.4639    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   29.0940   -3.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8426   -3.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0254   -3.2059    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.8978   -3.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7287   -3.1836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9522   -2.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3442   -3.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5179   -4.2815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2942   -4.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3304   -2.9345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8709   -4.2381    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   30.0397   -5.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8165   -5.2913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4316   -5.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4419   -5.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6293   -5.5845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7733   -6.4180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9128   -4.8307    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   23.7823   -2.1320    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   29.3196   -2.5472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1332   -2.6351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6142   -1.9754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2829   -1.2275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4658   -1.1432    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.9884   -1.8038    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  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
  5 11  1  0
  4 17  1  0
  8 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
  1 22  1  0
 22 23  2  0
 22 24  1  0
 15 25  1  0
 13 26  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
  9 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4229096

   ---

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: 505.45

Molecular Weight (Monoisotopic): 504.0248

AlogP: 6.87

#Rotatable Bonds: 6

Polar Surface Area: 80.90

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.07

CX Basic pKa: 4.18

CX LogP: 5.61

CX LogD: 3.26

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.29

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