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

ID: ALA4228529

PubChem CID: 124108546

Max Phase: Preclinical

Molecular Formula: C21H17Cl2N5O2S2

Molecular Weight: 506.44

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-c1cnccn1

Standard InChI:  InChI=1S/C21H17Cl2N5O2S2/c1-10(2)31-20-17(12-4-5-13(22)14(23)8-12)26-21(32-20)28-18(19(29)30)16(11(3)27-28)15-9-24-6-7-25-15/h4-10H,1-3H3,(H,29,30)

Standard InChI Key:  GLHVEXREDGAVAX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.4933  -21.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7477  -20.4208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0847  -19.9386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4260  -20.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1880  -20.6472    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.8498  -20.1678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5983  -19.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7811  -19.3892    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0787  -18.7336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8922  -18.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3733  -18.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0419  -17.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2248  -17.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7474  -17.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6396  -22.6053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7857  -21.7747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1858  -18.2487    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.5222  -16.7527    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.6266  -20.4214    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.7954  -21.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5722  -21.4746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1873  -21.7669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3819  -21.7670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9009  -22.4267    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2322  -23.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0493  -23.2590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5267  -22.5983    0.0000 N   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
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  3  6  1  0
 11 12  2  0
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 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
M  END

Alternative Forms

1. Parent:

   

   ALA4228529

   ---

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: 506.44

Molecular Weight (Monoisotopic): 505.0201

AlogP: 6.27

#Rotatable Bonds: 6

Polar Surface Area: 93.79

Molecular Species: ACID

HBA: 8

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.32

CX Basic pKa: 0.52

CX LogP: 5.31

CX LogD: 1.89

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.31

Np Likeness Score: -1.67

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