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

ID: ALA5280534

Max Phase: Preclinical

Molecular Formula: C24H22BrN5OS

Molecular Weight: 508.45

Names and Identifiers

Canonical SMILES:  CCc1ccccc1-n1nc(-c2cn(CC)c3ccc(Br)cc23)cc1/N=C1/NC(=O)CS1

Standard InChI:  InChI=1S/C24H22BrN5OS/c1-3-15-7-5-6-8-20(15)30-22(26-24-27-23(31)14-32-24)12-19(28-30)18-13-29(4-2)21-10-9-16(25)11-17(18)21/h5-13H,3-4,14H2,1-2H3,(H,26,27,31)

Standard InChI Key:  NVMGMWLXZOMZPR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   -0.1768    0.5702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    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
   -2.2738   -2.6845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3011    0.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1258    0.5702    0.0000 C   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
  5  4  1  0
  3  6  1  0
  6  7  2  0
  8  7  1  0
  8  9  1  0
  9 10  1  0
 11 10  1  0
  7 11  1  0
  9 12  2  0
  5 13  1  0
 14 13  2  0
 14 15  1  0
 15 16  1  0
 17 16  2  0
 13 17  1  0
 16 18  1  0
 19 18  2  0
 20 19  1  0
 21 20  2  0
 17 21  1  0
  2 22  1  0
 23 22  2  0
 24 23  1  0
 25 24  2  0
 26 25  1  0
 27 26  2  0
 22 27  1  0
 15 28  1  0
 20 29  1  0
 28 30  1  0
 27 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5280534

   ---

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: 508.45

Molecular Weight (Monoisotopic): 507.0728

AlogP: 5.69

#Rotatable Bonds: 5

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: 0.83

CX LogP: 6.40

CX LogD: 6.17

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.38

Np Likeness Score: -1.29

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