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

ID: ALA5281502

Max Phase: Preclinical

Molecular Formula: C21H16ClN5O2S

Molecular Weight: 437.91

Names and Identifiers

Canonical SMILES:  COc1ccc2[nH]cc(-c3cc(/N=C4/NC(=O)CS4)n(-c4cccc(Cl)c4)n3)c2c1

Standard InChI:  InChI=1S/C21H16ClN5O2S/c1-29-14-5-6-17-15(8-14)16(10-23-17)18-9-19(24-21-25-20(28)11-30-21)27(26-18)13-4-2-3-12(22)7-13/h2-10,23H,11H2,1H3,(H,24,25,28)

Standard InChI Key:  TXMKVCJJUJONHS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    0.8315    0.5702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0816   -0.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4281   -0.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2392   -0.2124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8782   -0.4471    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0916   -1.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8883   -1.4572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9217   -2.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1690   -2.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6518   -1.9360    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6360   -2.7106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0359   -0.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2493   -1.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0904   -1.2560    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3758   -0.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1449   -0.2012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2693    0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6260    1.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8529    0.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2438    1.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8316    1.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2435    2.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0684    2.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4801    2.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0721    1.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8395    1.9310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6360    2.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3048    2.0007    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
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  9 12  2  0
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  2 22  1  0
 23 22  2  0
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 25 24  2  0
 26 25  1  0
 27 26  2  0
 22 27  1  0
 20 28  1  0
 28 29  1  0
 26 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5281502

   ---

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: 437.91

Molecular Weight (Monoisotopic): 437.0713

AlogP: 4.53

#Rotatable Bonds: 4

Polar Surface Area: 84.30

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.57

CX Basic pKa: 0.88

CX LogP: 4.54

CX LogD: 4.31

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.49

Np Likeness Score: -1.24

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