2-[4-[(2,4-dioxothiazolidin-5-ylidene)methyl]phenoxy]-N-(4-methyl-1,3-benzothiazol-2-yl)acetamide

ID: ALA4796336

PubChem CID: 162675911

Max Phase: Preclinical

Molecular Formula: C20H15N3O4S2

Molecular Weight: 425.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cccc2sc(NC(=O)COc3ccc(/C=C4\SC(=O)NC4=O)cc3)nc12

Standard InChI:  InChI=1S/C20H15N3O4S2/c1-11-3-2-4-14-17(11)22-19(28-14)21-16(24)10-27-13-7-5-12(6-8-13)9-15-18(25)23-20(26)29-15/h2-9H,10H2,1H3,(H,21,22,24)(H,23,25,26)/b15-9-

Standard InChI Key:  ODUMFGAXJVJOJL-DHDCSXOGSA-N

Molfile:  

 
     RDKit          2D

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   21.9337  -25.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6458  -25.6782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3555  -25.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3527  -24.4378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6440  -24.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0630  -24.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7763  -24.4325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8639  -25.2484    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.6680  -25.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0781  -24.7060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.5248  -24.0968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0074  -26.1688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6912  -23.2926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2215  -25.6772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5100  -25.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7978  -25.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0863  -25.2628    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7972  -26.4974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3775  -25.6696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6340  -25.3390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2921  -26.4858    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.4924  -26.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0883  -25.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2758  -25.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8664  -26.6478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2755  -27.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0866  -27.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8695  -25.2351    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 24  1  0
 23 22  1  0
 22 20  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 25 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4796336

   ---

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: 425.49

Molecular Weight (Monoisotopic): 425.0504

AlogP: 3.95

#Rotatable Bonds: 5

Polar Surface Area: 97.39

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.19

CX Basic pKa: ┄

CX LogP: 3.94

CX LogD: 2.62

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.60

Np Likeness Score: -2.21

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