2-{[2-(4-Chlorophenyl)-1H-indol-3-ylmethylene]hydrazono}-5-(2-hydroxyethyl)thiazolidin-4-one

ID: ALA4553912

PubChem CID: 155555622

Max Phase: Preclinical

Molecular Formula: C20H17ClN4O2S

Molecular Weight: 412.90

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1N/C(=N/N=C/c2c(-c3ccc(Cl)cc3)[nH]c3ccccc23)SC1CCO

Standard InChI:  InChI=1S/C20H17ClN4O2S/c21-13-7-5-12(6-8-13)18-15(14-3-1-2-4-16(14)23-18)11-22-25-20-24-19(27)17(28-20)9-10-26/h1-8,11,17,23,26H,9-10H2,(H,24,25,27)/b22-11+

Standard InChI Key:  NZLXRCKLLQUKFA-SSDVNMTOSA-N

Molfile:  

 
     RDKit          2D

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    3.9708  -23.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7967  -23.0910    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.0537  -22.3060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3837  -21.8187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7180  -22.3060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8395  -22.0518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4525  -22.6054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2383  -22.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8513  -22.9047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0686  -23.4480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6565  -22.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5150  -24.0609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7624  -23.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0957  -24.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1804  -25.0262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9375  -25.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6010  -24.8769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9919  -21.9788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8144  -21.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1502  -21.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6645  -20.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8393  -20.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5073  -21.3142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9324  -22.0511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4845  -23.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6633  -23.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1770  -24.3386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9993  -19.7159    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  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
 26 27  1  0
 21 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4553912

   ---

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: 412.90

Molecular Weight (Monoisotopic): 412.0761

AlogP: 3.79

#Rotatable Bonds: 5

Polar Surface Area: 89.84

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.39

CX Basic pKa: ┄

CX LogP: 3.33

CX LogD: 3.02

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.44

Np Likeness Score: -0.72

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]

2. Schadich E,Kryshchyshyn-Dylevych A,Holota S,Polishchuk P,Džubak P,Gurska S,Hajduch M,Lesyk R.  (2020)  Assessing different thiazolidine and thiazole based compounds as antileishmanial scaffolds.,  30  (23.0): [PMID:33091607] [10.1016/j.bmcl.2020.127616]

Source

Source(1):

• Scientific Literature