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

ID: ALA5281614

Max Phase: Preclinical

Molecular Formula: C21H16ClN5OS

Molecular Weight: 421.91

Names and Identifiers

Canonical SMILES:  Cn1cc(-c2cc(/N=C3/NC(=O)CS3)n(-c3ccc(Cl)cc3)n2)c2ccccc21

Standard InChI:  InChI=1S/C21H16ClN5OS/c1-26-11-16(15-4-2-3-5-18(15)26)17-10-19(23-21-24-20(28)12-29-21)27(25-17)14-8-6-13(22)7-9-14/h2-11H,12H2,1H3,(H,23,24,28)

Standard InChI Key:  XIHIFBBFYMBMAQ-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   -0.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2447   -1.0615    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
    1.6949   -0.8043    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   -2.6554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856   -2.9408    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
    3.4526   -3.0677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2193   -0.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4327   -1.5796    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
   -2.5591   -0.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9115   -0.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3283   -0.5584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4526    0.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8093    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
    1.0605    0.9274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6483    1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0601    2.3534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8851    2.3534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2967    1.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8888    0.9274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6861   -2.3274    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
  3  4  2  0
  1  5  2  0
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  6  7  2  0
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  7 11  1  0
  9 12  2  0
  5 13  1  0
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 17 21  1  0
  2 22  1  0
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 24 23  1  0
 25 24  2  0
 26 25  1  0
 27 26  2  0
 22 27  1  0
 15 28  1  0
 25 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5281614

   ---

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: 421.91

Molecular Weight (Monoisotopic): 421.0764

AlogP: 4.53

#Rotatable Bonds: 3

Polar Surface Area: 64.21

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.57

CX Basic pKa: 0.87

CX LogP: 4.92

CX LogD: 4.69

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.53

Np Likeness Score: -1.33

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