(Z)-5-(4-methoxlbenzyliden)-2-thioxothiazolidin-4-one

ID: ALA224521

Chembl Id: CHEMBL224521

Cas Number: 81154-17-8

PubChem CID: 1241606

Max Phase: Preclinical

Molecular Formula: C11H9NO2S2

Molecular Weight: 251.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C2\SC(=S)NC2=O)cc1

Standard InChI:  InChI=1S/C11H9NO2S2/c1-14-8-4-2-7(3-5-8)6-9-10(13)12-11(15)16-9/h2-6H,1H3,(H,12,13,15)/b9-6-

Standard InChI Key:  ORGCJYCWFZQEFX-TWGQIWQCSA-N

Alternative Forms

1. Parent:

   

   ALA224521

   5-(p-Methoxybenzylidene)rhodanine

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: 251.33

Molecular Weight (Monoisotopic): 251.0075

AlogP: 2.18

#Rotatable Bonds: 2

Polar Surface Area: 38.33

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.93

CX Basic pKa: ┄

CX LogP: 2.58

CX LogD: 0.75

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.65

Np Likeness Score: -1.43

References

1. 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]

2. 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]

3. 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]

4. 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]

5. 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]

6. 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]

7. 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]

8. Trotsko N..  (2021)  Antitubercular properties of thiazolidin-4-ones - A review.,  215  [PMID:33588179] [10.1016/j.ejmech.2021.113266]

9. Christoff RM, Soares da Costa TP, Bayat S, Holien JK, Perugini MA, Abbott BM..  (2021)  Synthesis and structure-activity relationship studies of 2,4-thiazolidinediones and analogous heterocycles as inhibitors of dihydrodipicolinate synthase.,  52  [PMID:34826680] [10.1016/j.bmc.2021.116518]

Source

Source(1):

• Scientific Literature