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

ID: ALA487697

Chembl Id: CHEMBL487697

Cas Number: 6339-79-3

PubChem CID: 1241131

Max Phase: Preclinical

Molecular Formula: C10H7NO2S2

Molecular Weight: 237.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NC(=S)S/C1=C\c1ccc(O)cc1

Standard InChI:  InChI=1S/C10H7NO2S2/c12-7-3-1-6(2-4-7)5-8-9(13)11-10(14)15-8/h1-5,12H,(H,11,13,14)/b8-5-

Standard InChI Key:  RAYIDZVPIAJJPF-YVMONPNESA-N

Alternative Forms

1. Parent:

   

   ALA487697

   (Z)-5-(4-hydroxybenzylidene)-2-thioxothiazolidin-4-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: 237.31

Molecular Weight (Monoisotopic): 236.9918

AlogP: 1.88

#Rotatable Bonds: 1

Polar Surface Area: 49.33

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.93

CX Basic pKa: ┄

CX LogP: 2.44

CX LogD: 0.60

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.58

Np Likeness Score: -1.09

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. Russell AJ, Westwood IM, Crawford MH, Robinson J, Kawamura A, Redfield C, Laurieri N, Lowe ED, Davies SG, Sim E..  (2009)  Selective small molecule inhibitors of the potential breast cancer marker, human arylamine N-acetyltransferase 1, and its murine homologue, mouse arylamine N-acetyltransferase 2.,  17  (2): [PMID:19059786] [10.1016/j.bmc.2008.11.032]

3. Maccari R, Del Corso A, Giglio M, Moschini R, Mura U, Ottanà R..  (2011)  In vitro evaluation of 5-arylidene-2-thioxo-4-thiazolidinones active as aldose reductase inhibitors.,  21  (1): [PMID:21129963] [10.1016/j.bmcl.2010.11.041]

4. Liu J, Wu F, Chen L, Hu J, Zhao L, Chen C, Peng L..  (2011)  Evaluation of dihydropyrimidin-(2H)-one analogues and rhodanine derivatives as tyrosinase inhibitors.,  21  (8): [PMID:21411319] [10.1016/j.bmcl.2011.02.076]

5. Mendgen T, Steuer C, Klein CD..  (2012)  Privileged scaffolds or promiscuous binders: a comparative study on rhodanines and related heterocycles in medicinal chemistry.,  55  (2): [PMID:22077389] [10.1021/jm201243p]

6. Jadav SS, Sinha BN, Hilgenfeld R, Pastorino B, de Lamballerie X, Jayaprakash V..  (2015)  Thiazolidone derivatives as inhibitors of chikungunya virus.,  89  [PMID:25462237] [10.1016/j.ejmech.2014.10.042]

7.  (2011)  Low molecular weight MYC-MAX inhibitors, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data