2-{[2-Ethyl-6-(4-nitrophenyl)imidazo[2,1-b][1,3,4]thiadiazol-5-ylmethylene]hydrazono}-4-methyl-2,3-dihydrothiazole-5-carboxylic acid ethyl ester

ID: ALA4459134

PubChem CID: 155526898

Max Phase: Preclinical

Molecular Formula: C20H19N7O4S2

Molecular Weight: 485.55

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1s/c(=N\N=C\c2c(-c3ccc([N+](=O)[O-])cc3)nc3sc(CC)nn23)[nH]c1C

Standard InChI:  InChI=1S/C20H19N7O4S2/c1-4-15-25-26-14(10-21-24-19-22-11(3)17(33-19)18(28)31-5-2)16(23-20(26)32-15)12-6-8-13(9-7-12)27(29)30/h6-10H,4-5H2,1-3H3,(H,22,24)/b21-10+

Standard InChI Key:  WXIJEDKJMBDKCE-UFFVCSGVSA-N

Molfile:  

 
     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    9.3546   -6.2215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3362   -4.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8643   -5.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1289   -5.1253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1381   -5.9525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9279   -6.2023    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.4085   -5.5268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9130   -4.8622    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0419   -5.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6169   -4.8575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7905   -4.8687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3882   -5.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8141   -6.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6390   -6.2906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0702   -4.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2585   -3.9383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9924   -3.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1851   -2.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8393   -2.2508    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0220   -2.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8616   -3.1551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5799   -3.5569    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.2315   -5.5177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6508   -6.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4650   -1.7460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1143   -3.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4420   -3.0251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0394   -4.3195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6947   -3.3700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0224   -2.8953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5626   -5.6071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1619   -6.3260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1403   -4.9007    0.0000 O   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  2  0
 21 22  1  0
 22 18  1  0
  7 23  1  0
 23 24  1  0
 20 25  1  0
 21 26  1  0
 26 27  1  0
 26 28  2  0
 27 29  1  0
 29 30  1  0
 31 32  2  0
 31 33  1  0
 12 31  1  0
M  CHG  2  31   1  33  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4459134

   ---

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: 485.55

Molecular Weight (Monoisotopic): 485.0940

AlogP: 3.74

#Rotatable Bonds: 7

Polar Surface Area: 140.14

Molecular Species: ACID

HBA: 11

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.46

CX Basic pKa: 2.32

CX LogP: 4.40

CX LogD: 3.66

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.18

Np Likeness Score: -2.03

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