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

ID: ALA4521107

PubChem CID: 155542459

Max Phase: Preclinical

Molecular Formula: C20H19BrN6O2S2

Molecular Weight: 519.45

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H19BrN6O2S2/c1-4-15-26-27-14(16(24-20(27)30-15)12-6-8-13(21)9-7-12)10-22-25-19-23-11(3)17(31-19)18(28)29-5-2/h6-10H,4-5H2,1-3H3,(H,23,25)/b22-10+

Standard InChI Key:  OVMFREODPGKQFU-LSHDLFTRSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   21.8058   -6.2832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7874   -4.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3155   -5.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5799   -5.1870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5891   -6.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3789   -6.2639    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.8593   -5.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3640   -4.9239    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4932   -5.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0683   -4.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2420   -4.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8397   -5.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2655   -6.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0904   -6.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5214   -4.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7098   -4.0002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4437   -3.2173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6366   -3.0570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2908   -2.3129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4735   -2.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3132   -3.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0314   -3.6188    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.6823   -5.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1016   -6.2874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9165   -1.8081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5660   -3.5618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8938   -3.0872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4910   -4.3814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1466   -3.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4744   -2.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0168   -5.6659    0.0000 Br  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
 12 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4521107

   ---

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: 519.45

Molecular Weight (Monoisotopic): 518.0194

AlogP: 4.59

#Rotatable Bonds: 6

Polar Surface Area: 97.00

Molecular Species: ACID

HBA: 9

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.46

CX Basic pKa: 2.33

CX LogP: 5.23

CX LogD: 4.49

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.23

Np Likeness Score: -1.93

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