2-[4-[(2,4-dioxothiazolidin-5-ylidene)methyl]phenoxy]-N-(4-nitrophenyl)acetamide

ID: ALA4781378

PubChem CID: 18808548

Max Phase: Preclinical

Molecular Formula: C18H13N3O6S

Molecular Weight: 399.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(COc1ccc(/C=C2\SC(=O)NC2=O)cc1)Nc1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C18H13N3O6S/c22-16(19-12-3-5-13(6-4-12)21(25)26)10-27-14-7-1-11(2-8-14)9-15-17(23)20-18(24)28-15/h1-9H,10H2,(H,19,22)(H,20,23,24)/b15-9-

Standard InChI Key:  CGFXKUHDOBLVOB-DHDCSXOGSA-N

Molfile:  

 
     RDKit          2D

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    7.6133   -2.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6122   -3.7994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3243   -4.2124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0340   -3.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0312   -2.9721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3226   -2.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7415   -2.5608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4548   -2.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5425   -3.7827    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.3466   -3.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7566   -3.2403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2033   -2.6310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6859   -4.7031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3698   -1.8268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9000   -4.2115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1885   -3.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4763   -4.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7648   -3.7971    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4757   -5.0317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0561   -4.2039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3514   -3.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6431   -4.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6405   -5.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3521   -5.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0575   -5.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9310   -5.4206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9299   -6.2378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2238   -5.0111    0.0000 O   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
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
 10 13  2  0
 12 14  2  0
  2 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 26 27  2  0
 26 28  1  0
 23 26  1  0
M  CHG  2  26   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4781378

   2-[4-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]-N-(4-nitrophenyl)acetamide

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: 399.38

Molecular Weight (Monoisotopic): 399.0525

AlogP: 2.94

#Rotatable Bonds: 6

Polar Surface Area: 127.64

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.20

CX Basic pKa: ┄

CX LogP: 2.54

CX LogD: 1.39

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.43

Np Likeness Score: -1.86

References

1. Joshi H,Patil V,Tilekar K,Upadhyay N,Gota V,Ramaa CS.  (2020)  Benzylidene thiazolidinediones: Synthesis, in vitro investigations of antiproliferative mechanisms and in vivo efficacy determination in combination with Imatinib.,  30  (23.0): [PMID:32961322] [10.1016/j.bmcl.2020.127561]

Source

Source(1):

• Scientific Literature