5-(4-ethylbenzylidene)-2-thioxothiazolidin-4-one

ID: ALA443375

Chembl Id: CHEMBL443375

PubChem CID: 1271003

Max Phase: Preclinical

Molecular Formula: C12H11NOS2

Molecular Weight: 249.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1ccc(/C=C2\SC(=S)NC2=O)cc1

Standard InChI:  InChI=1S/C12H11NOS2/c1-2-8-3-5-9(6-4-8)7-10-11(14)13-12(15)16-10/h3-7H,2H2,1H3,(H,13,14,15)/b10-7-

Standard InChI Key:  SVXDHPADAXBMFB-YFHOEESVSA-N

Alternative Forms

1. Parent:

   

   ALA443375

   (5Z)-5-(4-ethylbenzylidene)-2-sulfanyl-1,3-thiazol-4(5H)-one

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: 249.36

Molecular Weight (Monoisotopic): 249.0282

AlogP: 2.74

#Rotatable Bonds: 2

Polar Surface Area: 29.10

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.93

CX Basic pKa: ┄

CX LogP: 3.70

CX LogD: 1.87

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.65

Np Likeness Score: -1.61

References

1. Mustata G, Follis AV, Hammoudeh DI, Metallo SJ, Wang H, Prochownik EV, Lazo JS, Bahar I..  (2009)  Discovery of novel Myc-Max heterodimer disruptors with a three-dimensional pharmacophore model.,  52  (5): [PMID:19215087] [10.1021/jm801278g]

2. Follis AV, Hammoudeh DI, Daab AT, Metallo SJ..  (2009)  Small-molecule perturbation of competing interactions between c-Myc and Max.,  19  (3): [PMID:19114306] [10.1016/j.bmcl.2008.12.025]

3. Yap JL, Chauhan J, Jung K, Chen L, Prochownik EV, Fletcher S.  (2012)  Small-molecule inhibitors of dimeric transcription factors: Antagonism of proteinprotein and proteinDNA interactions,  3  (5): [10.1039/C2MD00289B]

4. Jung KY, Wang H, Teriete P, Yap JL, Chen L, Lanning ME, Hu A, Lambert LJ, Holien T, Sundan A, Cosford ND, Prochownik EV, Fletcher S..  (2015)  Perturbation of the c-Myc-Max protein-protein interaction via synthetic α-helix mimetics.,  58  (7): [PMID:25734936] [10.1021/jm501440q]

5.  (2011)  Low molecular weight MYC-MAX inhibitors, 

6.  (2014)  Linked Myc-max small molecule inhibitors, 

7. Carabet LA, Lallous N, Leblanc E, Ban F, Morin H, Lawn S, Ghaidi F, Lee J, Mills IG, Gleave ME, Rennie PS, Cherkasov A..  (2018)  Computer-aided drug discovery of Myc-Max inhibitors as potential therapeutics for prostate cancer.,  160  [PMID:30326371] [10.1016/j.ejmech.2018.09.023]

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data