N-(3,4-dibromophenyl)-2,4-5-(furan-2-ylmethylene)-2,4-dioxothiazolidin-3-yl)acetamide

ID: ALA4781695

PubChem CID: 162664243

Max Phase: Preclinical

Molecular Formula: C16H10Br2N2O4S

Molecular Weight: 486.14

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CN1C(=O)S/C(=C/c2ccco2)C1=O)Nc1ccc(Br)c(Br)c1

Standard InChI:  InChI=1S/C16H10Br2N2O4S/c17-11-4-3-9(6-12(11)18)19-14(21)8-20-15(22)13(25-16(20)23)7-10-2-1-5-24-10/h1-7H,8H2,(H,19,21)/b13-7+

Standard InChI Key:  LSNHKNKJHSRFIN-NTUHNPAUSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   23.7026  -12.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5240  -12.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7825  -12.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1154  -11.5315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4525  -12.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5641  -11.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1707  -12.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0872  -13.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8374  -13.4640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.3892  -12.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9774  -12.1410    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   28.2060  -12.9398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0062  -14.2677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3982  -14.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5670  -15.6174    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9548  -16.1675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1743  -15.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5625  -16.4577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7351  -17.2624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5209  -17.5189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1253  -16.9679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6172  -14.5601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3755  -13.5394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1280  -17.8094    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   25.6928  -18.3179    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  1  2  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  7  1  0
 10 12  2  0
  9 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 14 22  2  0
  8 23  2  0
 19 24  1  0
 20 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4781695

   ---

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: 486.14

Molecular Weight (Monoisotopic): 483.8728

AlogP: 4.48

#Rotatable Bonds: 4

Polar Surface Area: 79.62

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.15

CX Basic pKa: ┄

CX LogP: 3.58

CX LogD: 3.58

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.65

Np Likeness Score: -2.22

References

1. Tilekar K,Upadhyay N,Hess JD,Macias LH,Mrowka P,Aguilera RJ,Meyer-Almes FJ,Iancu CV,Choe JY,Ramaa CS.  (2020)  Structure guided design and synthesis of furyl thiazolidinedione derivatives as inhibitors of GLUT 1 and GLUT 4, and evaluation of their anti-leukemic potential.,  202  [PMID:32634629] [10.1016/j.ejmech.2020.112603]

Source

Source(1):

• Scientific Literature