3-(2-aminoethyl)-5-(4-fluorobenzylidene)thiazolidine-2,4-dione

ID: ALA569743

Cas Number: 779314-09-9

PubChem CID: 2322406

Max Phase: Preclinical

Molecular Formula: C12H11FN2O2S

Molecular Weight: 266.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCN1C(=O)S/C(=C\c2ccc(F)cc2)C1=O

Standard InChI:  InChI=1S/C12H11FN2O2S/c13-9-3-1-8(2-4-9)7-10-11(16)15(6-5-14)12(17)18-10/h1-4,7H,5-6,14H2/b10-7-

Standard InChI Key:  SWPLPGAZGUFJJB-YFHOEESVSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
   -4.2427   -7.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2439   -8.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5290   -8.5768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8127   -8.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8156   -7.3331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5308   -6.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1027   -6.9179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3862   -7.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1398   -8.1141    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3149   -8.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517   -7.3396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7151   -6.8488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1635   -8.7941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7075   -6.0239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6644   -6.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3771   -7.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0932   -6.9363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9586   -8.5759    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  2  3  1  0
  5  6  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
  6  1  1  0
 10 13  2  0
  1  2  2  0
 12 14  2  0
  5  7  1  0
 11 15  1  0
  3  4  2  0
 15 16  1  0
  7  8  2  0
 16 17  1  0
  8  9  1  0
  2 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA569743

   3-(2-Aminoethyl)-5-[(4-fluorophenyl)methylidene]-1,3-thiazolidine-2,4-dione

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 266.30

Molecular Weight (Monoisotopic): 266.0525

AlogP: 1.82

#Rotatable Bonds: 3

Polar Surface Area: 63.40

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.14

CX LogP: 1.42

CX LogD: -0.31

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.85

Np Likeness Score: -1.88

References

1. Li Q, Al-Ayoubi A, Guo T, Zheng H, Sarkar A, Nguyen T, Eblen ST, Grant S, Kellogg GE, Zhang S..  (2009)  Structure-activity relationship (SAR) studies of 3-(2-amino-ethyl)-5-(4-ethoxy-benzylidene)-thiazolidine-2,4-dione: development of potential substrate-specific ERK1/2 inhibitors.,  19  (21): [PMID:19796943] [10.1016/j.bmcl.2009.09.057]

Source

Source(1):

• Scientific Literature