5-[1-Phenyl-meth-(Z)-ylidene]-2-thioxo-thiazolidin-4-one

ID: ALA305763

Chembl Id: CHEMBL305763

Cas Number: 3806-42-6

PubChem CID: 1273210

Max Phase: Preclinical

Molecular Formula: C10H7NOS2

Molecular Weight: 221.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NC(=S)S/C1=C\c1ccccc1

Standard InChI:  InChI=1S/C10H7NOS2/c12-9-8(14-10(13)11-9)6-7-4-2-1-3-5-7/h1-6H,(H,11,12,13)/b8-6-

Standard InChI Key:  OONWCXLYKDWKOU-VURMDHGXSA-N

Alternative Forms

1. Parent:

   

   ALA305763

   5-Benzylidenerhodanine

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: 221.31

Molecular Weight (Monoisotopic): 220.9969

AlogP: 2.18

#Rotatable Bonds: 1

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: 2.74

CX LogD: 0.91

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.58

Np Likeness Score: -1.63

References

1. Grant EB, Guiadeen D, Baum EZ, Foleno BD, Jin H, Montenegro DA, Nelson EA, Bush K, Hlasta DJ..  (2000)  The synthesis and SAR of rhodanines as novel class C beta-lactamase inhibitors.,  10  (19): [PMID:11012024] [10.1016/s0960-894x(00)00444-3]

2. Sortino M, Delgado P, Juárez S, Quiroga J, Abonía R, Insuasty B, Nogueras M, Rodero L, Garibotto FM, Enriz RD, Zacchino SA..  (2007)  Synthesis and antifungal activity of (Z)-5-arylidenerhodanines.,  15  (1): [PMID:17049255] [10.1016/j.bmc.2006.09.038]

3. Irvine MW, Patrick GL, Kewney J, Hastings SF, MacKenzie SJ..  (2008)  Rhodanine derivatives as novel inhibitors of PDE4.,  18  (6): [PMID:18304812] [10.1016/j.bmcl.2008.01.117]

4. 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]

5. Fan C, Clay MD, Deyholos MK, Vederas JC..  (2010)  Exploration of inhibitors for diaminopimelate aminotransferase.,  18  (6): [PMID:20185317] [10.1016/j.bmc.2010.02.001]

6. PubChem BioAssay data set, 

7. Heng S, Tieu W, Hautmann S, Kuan K, Pedersen DS, Pietsch M, Gütschow M, Abell AD..  (2011)  New cholesterol esterase inhibitors based on rhodanine and thiazolidinedione scaffolds.,  19  (24): [PMID:22075233] [10.1016/j.bmc.2011.10.042]

8. 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]

9. Zvarec O, Polyak SW, Tieu W, Kuan K, Dai H, Pedersen DS, Morona R, Zhang L, Booker GW, Abell AD..  (2012)  5-benzylidenerhodanine and 5-benzylidene-2-4-thiazolidinedione based antibacterials.,  22  (8): [PMID:22444680] [10.1016/j.bmcl.2012.02.100]

10. Chrysanthopoulos PK, Mujumdar P, Woods LA, Dolezal O, Ren B, Peat TS, Poulsen SA..  (2017)  Identification of a New Zinc Binding Chemotype by Fragment Screening.,  60  (17): [PMID:28817930] [10.1021/acs.jmedchem.7b00606]

11. Bataille CJ, Brennan MB, Byrne S, Davies SG, Durbin M, Fedorov O, Huber KV, Jones AM, Knapp S, Liu G, Nadali A, Quevedo CE, Russell AJ, Walker RG, Westwood R, Wynne GM..  (2017)  Thiazolidine derivatives as potent and selective inhibitors of the PIM kinase family.,  25  (9): [PMID:28341403] [10.1016/j.bmc.2017.02.056]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays