Acetic acid 2-(2-{[2-(4-chlorophenyl)-1H-indol-3-ylmethylene]hydrazono}-4-oxo-thiazolidin-5-yl)ethyl ester

ID: ALA4555640

PubChem CID: 155557076

Max Phase: Preclinical

Molecular Formula: C22H19ClN4O3S

Molecular Weight: 454.94

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)OCCC1S/C(=N\N=C\c2c(-c3ccc(Cl)cc3)[nH]c3ccccc23)NC1=O

Standard InChI:  InChI=1S/C22H19ClN4O3S/c1-13(28)30-11-10-19-21(29)26-22(31-19)27-24-12-17-16-4-2-3-5-18(16)25-20(17)14-6-8-15(23)9-7-14/h2-9,12,19,25H,10-11H2,1H3,(H,26,27,29)/b24-12+

Standard InChI Key:  WNGSIVFOYNKSSO-WYMPLXKRSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   14.7294  -23.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5551  -23.0576    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.8122  -22.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1423  -21.7856    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4767  -22.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5978  -22.0187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2107  -22.5721    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9963  -22.3180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6093  -22.8714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8262  -23.4146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4143  -22.6990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2728  -24.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5203  -23.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8539  -24.1723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9384  -24.9925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6955  -25.3277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3588  -24.8432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7495  -21.9456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5720  -21.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9078  -21.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4222  -20.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5971  -20.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2650  -21.2812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6913  -22.0180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2433  -23.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4221  -23.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7569  -19.6832    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.9360  -24.3050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1149  -24.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6287  -24.8850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7799  -23.4629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  3  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 13  1  0
 12 10  1  0
 10 11  1  0
 11  9  2  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 11 18  1  0
  5 24  2  0
  1 25  1  0
 25 26  1  0
 21 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4555640

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 454.94

Molecular Weight (Monoisotopic): 454.0866

AlogP: 4.36

#Rotatable Bonds: 6

Polar Surface Area: 95.91

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.34

CX Basic pKa: ┄

CX LogP: 3.77

CX LogD: 3.44

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.33

Np Likeness Score: -0.62

References

1. Kryshchyshyn A, Kaminskyy D, Karpenko O, Gzella A, Grellier P, Lesyk R..  (2019)  Thiazolidinone/thiazole based hybrids - New class of antitrypanosomal agents.,  174  [PMID:31051403] [10.1016/j.ejmech.2019.04.052]

Source

Source(1):

• Scientific Literature