911714-34-6

Basic information

• Product Name: 2,4-Thiazolidinedione, 5-[(4-hydroxy-3-methoxyphenyl)methylene]-, (5Z)-
• CAS NO: 911714-34-6
• Molecular Formula: C11H9NO4S
• Molecular Weight: 251.263
• Mol File: 911714-34-6.mol
• Article Data: 22

Chemical Properties

• CAS DataBase Reference: 2,4-Thiazolidinedione, 5-[(4-hydroxy-3-methoxyphenyl)methylene]-, (5Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Thiazolidinedione, 5-[(4-hydroxy-3-methoxyphenyl)methylene]-, (5Z)-(911714-34-6)
• EPA Substance Registry System: 2,4-Thiazolidinedione, 5-[(4-hydroxy-3-methoxyphenyl)methylene]-, (5Z)-(911714-34-6)

Safety Data

• Hazardous Substances Data: 911714-34-6(Hazardous Substances Data)

Upstream product

• 2295-31-0 thiazoline-2,4-dione 
• 121-33-5 vanillin 

Downstream Products

• 1039558-88-7 C₁₃H₁₂N₂O₅S 
• 1020066-80-1 (Z)-5-(4-hydroxy-3-methoxybenzylidene)-3-(1-methylcyclohexylmethyl)thiazolidine-2,4-dione 
• 1369567-95-2 3-benzyl-5-{(Z)-1-[4-(benzyloxy)-3-methoxyphenyl]methylidene}-1,3-thiazolane-2,4-dione 

Relevant articles and documents

Discovery of 5-(3-bromo-2-(2,3-dibromo-4,5-dimethoxybenzyl)-4,5-dimethoxybenzylidene)thiazolidine-2,4-dione as a novel potent protein tyrosine phosphatase 1B inhibitor with antidiabetic properties

Protein tyrosine phosphatase 1B (PTP1B) is a well-validated target in therapeutic interventions for type 2 diabetes mellitus (T2DM), however, PTP1B inhibitors containing negatively charged nonhydrolyzable pTyr mimetics are difficult to convert to the corr

Antileishmanial activity evaluation of thiazolidine-2,4-dione against Leishmania infantum and Leishmania braziliensis

Leishmaniasis is responsible for approximately 65,000 annual deaths. Despite the mortality data, drugs available for the treatment of patients are insufficient and have moderate therapeutic efficacy in addition to serious adverse effects, which makes the development of new drugs urgent. To achieve this goal, the integration of kinetic and DSF assays against parasitic validated targets, along with phenotypic assays, can help the identification and optimization of bioactive compounds. Pteridine reductase 1 (PTR1), a validated target in Leishmania sp., is responsible for the reduction of folate and biopterin to tetrahydrofolate and tetrahydrobiopterin, respectively, both of which are essential for cell growth. In addition to the in vitro evaluation of 16 thiazolidine-2,4-dione derivatives against Leishmania major PTR1 (LmPTR1), using the differential scanning fluorimetry (ThermoFluor), phenotypic assays were employed to evaluate the compound effect over Leishmania braziliensis (MHOM/BR/75/M2903) and Leishmania infantum (MHOM/BR/74/PP75) promastigotes viability. The ThermoFluor results show that thiazolidine-2,4-dione derivatives have micromolar affinity to the target and equivalent activity on Leishmania cells. 2b is the most potent compound against L. infantum (EC50 = 23.45 ± 4.54 μM), whereas 2a is the most potent against L. braziliensis (EC50 = 44.16 ± 5.77 μM). This result suggests that lipophilic substituents on either—meta and/or—para positions of the benzylidene ring increase the potency against L. infantum. On the other hand, compound 2c (CE50 = 49.22 ± 7.71 μM) presented the highest selectivity index.

THIAZOLIDINEDIONE DERIVATIVE AND USE THEREOF

Provided are a novel compound represented by any one of Formulae 1a and 1b and use thereof. Provided are novel thiazolidinedione derivatives represented by any one of Formulae 1a and 1b and pharmaceutical compositions containing the same.