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

ID: ALA4753636

PubChem CID: 162653715

Max Phase: Preclinical

Molecular Formula: C19H15BrN2O4S

Molecular Weight: 447.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(Br)ccc1NC(=O)COc1ccc(/C=C2\SC(=O)NC2=O)cc1

Standard InChI:  InChI=1S/C19H15BrN2O4S/c1-11-8-13(20)4-7-15(11)21-17(23)10-26-14-5-2-12(3-6-14)9-16-18(24)22-19(25)27-16/h2-9H,10H2,1H3,(H,21,23)(H,22,24,25)/b16-9-

Standard InChI Key:  HBFAHIRHKNEWGK-SXGWCWSVSA-N

Molfile:  

 
     RDKit          2D

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    7.4606  -15.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4595  -16.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1716  -16.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8813  -16.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8785  -15.6551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1698  -15.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5888  -15.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3021  -15.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3898  -16.4657    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.1939  -16.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6039  -15.9233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0506  -15.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5332  -17.3861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2171  -14.5098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7473  -16.8945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0358  -16.4812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3236  -16.8934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6121  -16.4801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3230  -17.7147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9033  -16.8868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1987  -16.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4904  -16.8816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4878  -17.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1994  -18.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9048  -17.7015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7796  -18.1073    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.6131  -18.1090    0.0000 C   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
 23 26  1  0
 25 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4753636

   ---

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: 447.31

Molecular Weight (Monoisotopic): 445.9936

AlogP: 4.10

#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: 3.89

CX LogD: 2.73

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.67

Np Likeness Score: -1.87

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