Generation of a library of 4-thiazolidinones utilizing polymer supported quench (PSQ) reagent methodology

Ault-Justus, Stephanie E.; Hodges, John C.; Wilson, Michael W.

doi:10.1002/(sici)1097-0290(199824)61:1<17::aid-bit6>3.0.co;2-1

Cited by 35 publications

(11 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Polymer supported quench reagents are polymer-tethered functional groups (nucleophilic/electrophilic) that were used to remove the excess reagents from the reaction mixture containing the product. Poly(styrene-codivinylbenzene) (as polymer) functionalized with tris(2aminoethyl)amine and 2-amino-ethane-thiol (as two functional groups) were basically used to remove the excess aldehyde and mercapto acid, respectively [20].…”

Section: -Thiazolidinonesmentioning

confidence: 99%

“…Compound (20) was investigated as an FSHR positive allosteric modulator, and it was found that the compound in a dose-dependent manner stimulated cAMP production, activated AKT and ERK signaling pathways, and induced estradiol production in cultured human granulosa cells. However, pharmacokinetic and safety investigations revealed poor oral availability and genotoxcity [94].…”

Section: -Thiazolidinones As Type III Secretion System Inhibitormentioning

confidence: 99%

See 1 more Smart Citation

Thiazolidinones: Synthesis, Reactivity, and Their Biological Applications

Nirwan

Chahal

Kakkar

2019

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

Thiazolidinone is a biologically important five‐membered heterocyclic ring having almost all types of biological activities. This review covers various types of thiazolidinones, such as 2‐thiazolidinones, 4‐thiazolidinones, 5‐thiazolidinones, 2‐thioxo‐4‐thiazolidinones, and thiazolidiene‐2,4‐dione. The literature related to the physical properties, chemical reactions, and synthesis for these derivatives has been included. Recent advances in the biological activities reported for 4‐thiazolidinone derivatives, such as peroxisome proliferator‐activated receptor γ binders, follicle‐stimulating hormone agonists, cystic fibrosis transmembrane conductance regulator inhibitors, and antioxidants, have been covered in this review. Thus, this study may help in further optimizing these thiazolidinone derivatives as more effective drug agents.

show abstract

Section: -Thiazolidinonesmentioning

confidence: 99%

Section: -Thiazolidinones As Type III Secretion System Inhibitormentioning

confidence: 99%

Thiazolidinones: Synthesis, Reactivity, and Their Biological Applications

Nirwan

Chahal

Kakkar

2019

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

show abstract

“…Two resins are also used in the generation of 4-thiazolidinones. 143 The ability to combine the use of supported reagents and scavengers (supported reagents delivering an additional reactant necessary for the reaction to proceed, and scavengers removing starting materials and by-products) enhances the utility of this approach for medicinal chemists. For example, the use of polymer-supported amine bases and nucleophilic or electrophilic scavenger resins has been reported by a number of groups in the synthesis of amides (from amines and acid chlorides), sulfonamides (from amines and sulfonyl chlorides), tertiary amines (from secondary amines and alkylating agents) and pyrazoles (from ␤-diketones and hydrazines) (see Refs.…”

Section: P O L Y M E R -S U P P O R T E D S C a V E N G E R R E A G E N T Smentioning

confidence: 99%

Solid-supported reagents in organic synthesis

Drewry¹,

Coe²,

Poon³

1999

Med. Res. Rev.

139

View full text Add to dashboard Cite

The current interest in solid-phase organic synthesis has led to a renewed interest in a complementary technique in which solid supported reagents are used in solution phase chemistry. This technique obviates the need for attachment of the substrate to a solid-support, and enables the chemist to monitor the reactions using familiar analytical techniques. The purpose of this review is to increase awareness of the wide range of useful transformations which can be accomplished using solid-supported reagents.

show abstract

“…18 A similar mixed amide synthesis which uses a mixture of 1 and 7 in the purification step has also been described. 8 In the latter situation (Scheme 17), 19 the syntheses of 4-thiazolidinones have been achieved by employing either polyamine resin 1 or cystamine resin 3 plus basic alumina to remove starting aldehyde, starting thioglycolic acid, and some additonal polar impurities from the desired product. Multiple chemical mechanisms by which these resins achieve this purification are conceivable.…”

Section: Purification Of Multicomponent Reactionsmentioning

confidence: 99%