N-(3-chloro-4-methylphenyl)-2-[4-[(2,4-dioxothiazolidin-5-ylidene)methyl]phenoxy]acetamide

ID: ALA4797525

PubChem CID: 49890615

Max Phase: Preclinical

Molecular Formula: C19H15ClN2O4S

Molecular Weight: 402.86

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccc(NC(=O)COc2ccc(/C=C3\SC(=O)NC3=O)cc2)cc1Cl

Standard InChI:  InChI=1S/C19H15ClN2O4S/c1-11-2-5-13(9-15(11)20)21-17(23)10-26-14-6-3-12(4-7-14)8-16-18(24)22-19(25)27-16/h2-9H,10H2,1H3,(H,21,23)(H,22,24,25)/b16-8-

Standard InChI Key:  DKMKNOQELNTRJX-PXNMLYILSA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   32.8100  -15.3533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8089  -16.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5211  -16.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2307  -16.1764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2279  -15.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5193  -14.9444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9382  -14.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6516  -15.3443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7392  -16.1602    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   36.5433  -16.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9534  -15.6178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.4001  -15.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8826  -17.0807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.5665  -14.2044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.0967  -16.5891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3852  -16.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6731  -16.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9616  -16.1747    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6724  -17.4093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2528  -16.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5481  -16.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8398  -16.5762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8372  -17.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5489  -17.8045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2542  -17.3961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5496  -18.6217    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.1290  -17.8019    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
 24 26  1  0
 23 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4797525

   N-(3-chloro-4-methylphenyl)-2-[4-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]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: 402.86

Molecular Weight (Monoisotopic): 402.0441

AlogP: 3.99

#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: 3.72

CX LogD: 2.57

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.74

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