4-[3-(4-Bromo-phenyl)-2-(4-bromo-phenylimino)-4-oxo-thiazolidin-5-ylidenemethyl]-benzoic acid

ID: ALA2297518

PubChem CID: 76334938

Max Phase: Preclinical

Molecular Formula: C23H14Br2N2O3S

Molecular Weight: 558.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(/C=C2/S/C(=N\c3ccc(Br)cc3)N(c3ccc(Br)cc3)C2=O)cc1

Standard InChI:  InChI=1S/C23H14Br2N2O3S/c24-16-5-9-18(10-6-16)26-23-27(19-11-7-17(25)8-12-19)21(28)20(31-23)13-14-1-3-15(4-2-14)22(29)30/h1-13H,(H,29,30)/b20-13+,26-23-

Standard InChI Key:  MCVFXWMDHUVAMM-VOYPSTMSSA-N

Molfile:  

     RDKit          2D

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   21.9348   -3.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9337   -4.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6417   -4.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3514   -4.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3485   -3.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6399   -2.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0597   -4.4210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7668   -4.0113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5102   -4.3413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.0561   -3.7332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6463   -3.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8473   -3.1973    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.8689   -3.8173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9775   -2.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7900   -2.1922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2717   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0836   -2.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4155   -2.0239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9295   -1.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1193   -1.4514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6807   -5.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0724   -5.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2429   -6.4827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0211   -6.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6290   -6.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4555   -5.3861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2289   -1.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7112   -2.5943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.5591   -1.1871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2270   -2.7860    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   26.1931   -7.5337    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  2  0
  8  9  1  0
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 10 13  2  0
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 19 20  2  0
 20 15  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
  9 21  1  0
 27 28  1  0
 27 29  2  0
 18 27  1  0
  1 30  1  0
 24 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2297518

   4-[(E)-[3-(4-bromophenyl)-2-(4-bromophenyl)imino-4-oxo-1,3-thiazolidin-5-ylidene]methyl]benzoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 558.25

Molecular Weight (Monoisotopic): 555.9092

AlogP: 6.72

#Rotatable Bonds: 4

Polar Surface Area: 69.97

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.07

CX Basic pKa: ┄

CX LogP: 6.99

CX LogD: 3.87

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.36

Np Likeness Score: -1.30

References

1. Zhao D, Liu H, Zheng L, He G, Qu D, Han S.  (2013)  Synthesis of novel 4-thiazolidione derivatives as antibacterial agents against drug-resistant Staphylococcus epidermidis,  22  (8): [10.1007/s00044-012-0363-9]

Source

Source(1):

• Scientific Literature