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

ID: ALA5287241

Max Phase: Preclinical

Molecular Formula: C22H17BrClN5OS

Molecular Weight: 514.84

Names and Identifiers

Canonical SMILES:  CCn1cc(-c2cc(/N=C3/NC(=O)CS3)n(-c3ccc(Cl)cc3)n2)c2cc(Br)ccc21

Standard InChI:  InChI=1S/C22H17BrClN5OS/c1-2-28-11-17(16-9-13(23)3-8-19(16)28)18-10-20(25-22-26-21(30)12-31-22)29(27-18)15-6-4-14(24)5-7-15/h3-11H,2,12H2,1H3,(H,25,26,30)

Standard InChI Key:  IBGOCTQTYRHZLN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    0.6481    0.2131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8982   -0.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2447   -1.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4226   -0.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6948   -0.8042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9083   -1.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7049   -1.8143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7384   -2.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856   -2.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4684   -2.2931    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4527   -3.0677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2192   -0.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4327   -1.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2737   -1.6131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5592   -0.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3283   -0.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4527    0.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8094    0.7772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0363    0.4798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0604    0.9274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6483    1.6418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0600    2.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8850    2.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2967    1.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8887    0.9274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6861   -2.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0228    1.5739    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.2737   -3.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2974    3.0677    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
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 20 29  1  0
 28 30  1  0
 25 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5287241

   ---

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: 514.84

Molecular Weight (Monoisotopic): 513.0026

AlogP: 5.78

#Rotatable Bonds: 4

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: 0.79

CX LogP: 6.04

CX LogD: 5.82

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.38

Np Likeness Score: -1.52

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