(2Z)-2-{[3-(5-bromo-1-methyl-1H-indol-3-yl)-1-(3-chlorophenyl)-1H-pyrazol-5-yl]imino}-1,3-thiazolidin-4-one

ID: ALA5290278

Max Phase: Preclinical

Molecular Formula: C21H15BrClN5OS

Molecular Weight: 500.81

Names and Identifiers

Canonical SMILES:  Cn1cc(-c2cc(/N=C3/NC(=O)CS3)n(-c3cccc(Cl)c3)n2)c2cc(Br)ccc21

Standard InChI:  InChI=1S/C21H15BrClN5OS/c1-27-10-16(15-7-12(22)5-6-18(15)27)17-9-19(24-21-25-20(29)11-30-21)28(26-17)14-4-2-3-13(23)8-14/h2-10H,11H2,1H3,(H,24,25,29)

Standard InChI Key:  OBMCGOBTQZHKOP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    0.6481    0.5702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8982   -0.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2447   -0.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4226   -0.2124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6948   -0.4471    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9083   -1.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7049   -1.4572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7384   -2.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856   -2.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4684   -1.9360    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4526   -2.7106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2193   -0.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4327   -1.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2738   -1.2560    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5592   -0.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9115    0.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3283   -0.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4526    0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8094    1.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0363    0.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0604    1.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6482    1.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0601    2.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8850    2.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2967    2.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8887    1.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6861   -1.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0229    1.9309    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.1214    2.0006    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  9 12  2  0
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  2 22  1  0
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 25 24  2  0
 26 25  1  0
 27 26  2  0
 22 27  1  0
 15 28  1  0
 20 29  1  0
 26 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5290278

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 500.81

Molecular Weight (Monoisotopic): 498.9869

AlogP: 5.30

#Rotatable Bonds: 3

Polar Surface Area: 64.21

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.57

CX Basic pKa: 0.80

CX LogP: 5.69

CX LogD: 5.46

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.42

Np Likeness Score: -1.47

References

1. Soni JP, Chilvery S, Sharma A, Reddy GN, Godugu C, Shankaraiah N..  (2023)  Design, synthesis and in vitro cytotoxicity evaluation of indolo-pyrazoles grafted with thiazolidinone as tubulin polymerization inhibitors.,  14  (3): [PMID:36970141] [10.1039/d2md00442a]

Source

Source(1):

• Scientific Literature