N-[2-chloro-4-(trifluoromethyl)phenyl]-2-[4-[(2,4-dioxothiazolidin-5-ylidene)methyl]phenoxy]acetamide

ID: ALA4759958

PubChem CID: 162658405

Max Phase: Preclinical

Molecular Formula: C19H12ClF3N2O4S

Molecular Weight: 456.83

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(COc1ccc(/C=C2\SC(=O)NC2=O)cc1)Nc1ccc(C(F)(F)F)cc1Cl

Standard InChI:  InChI=1S/C19H12ClF3N2O4S/c20-13-8-11(19(21,22)23)3-6-14(13)24-16(26)9-29-12-4-1-10(2-5-12)7-15-17(27)25-18(28)30-15/h1-8H,9H2,(H,24,26)(H,25,27,28)/b15-7-

Standard InChI Key:  MWQWZNSUMSXNJT-CHHVJCJISA-N

Molfile:  

 
     RDKit          2D

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   20.4696  -22.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4685  -23.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1807  -23.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8903  -23.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8875  -22.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1789  -22.1051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5978  -22.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3112  -22.5051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3988  -23.3210    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.2029  -23.4920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6130  -22.7786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.0597  -22.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5422  -24.2414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2261  -21.3651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7563  -23.7498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0448  -23.3365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3327  -23.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6212  -23.3354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3320  -24.5700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9124  -23.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2077  -23.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4994  -23.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4968  -24.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2084  -24.9653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9138  -24.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6221  -24.9644    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.7886  -24.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0814  -24.5531    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.7875  -25.7798    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.0780  -25.3659    0.0000 F   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
 25 26  1  0
 23 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4759958

   ---

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: 456.83

Molecular Weight (Monoisotopic): 456.0158

AlogP: 4.70

#Rotatable Bonds: 5

Polar Surface Area: 84.50

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.20

CX Basic pKa: ┄

CX LogP: 4.09

CX LogD: 2.93

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.64

Np Likeness Score: -1.97

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