Acetic acid 2-{2-[(2-allylsulfanyl-6-phenylimidazo[2,1-b][1,3,4]thiadiazol-5-ylmethylene)hydrazono]-4-oxothiazolidin-5-yl}ethyl ester

ID: ALA4524672

PubChem CID: 155538500

Max Phase: Preclinical

Molecular Formula: C21H20N6O3S3

Molecular Weight: 500.63

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CCSc1nn2c(/C=N/N=C3/NC(=O)C(CCOC(C)=O)S3)c(-c3ccccc3)nc2s1

Standard InChI:  InChI=1S/C21H20N6O3S3/c1-3-11-31-21-26-27-15(17(23-20(27)33-21)14-7-5-4-6-8-14)12-22-25-19-24-18(29)16(32-19)9-10-30-13(2)28/h3-8,12,16H,1,9-11H2,2H3,(H,24,25,29)/b22-12+

Standard InChI Key:  YULCKLSWLHFMQF-WSDLNYQXSA-N

Molfile:  

 
     RDKit          2D

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    8.6891  -14.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2182  -14.7238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4799  -14.2922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   10.2623  -14.0299    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3977  -14.7363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9736  -14.0251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1491  -14.0362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7476  -14.7577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1725  -15.4696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9956  -15.4550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4236  -13.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3483  -12.3267    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5384  -12.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1866  -11.4223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3671  -11.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2084  -12.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9298  -12.7301    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8085  -10.9143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4591  -12.6756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7834  -12.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0384  -12.5483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3627  -12.0757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6134  -12.4210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4361  -11.2536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5779  -14.6839    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.9963  -15.3904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8175  -15.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2360  -16.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  2  0
  4  2  1  0
  2  3  2  0
  3  1  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  4  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  3  9  1  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 20 23  2  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
  7 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4524672

   ---

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: 500.63

Molecular Weight (Monoisotopic): 500.0759

AlogP: 3.61

#Rotatable Bonds: 9

Polar Surface Area: 110.31

Molecular Species: NEUTRAL

HBA: 11

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.34

CX Basic pKa: 1.67

CX LogP: 4.20

CX LogD: 3.87

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.16

Np Likeness Score: -1.30

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