RHODANINES. I. DERIVATIVES OF Β-Phenylethylamines

Buck, Johannes S.; Leonard, Clifford S.

doi:10.1021/ja01358a034

Cited by 6 publications

(3 citation statements)

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“…The 4‐thiazolidinones having no aryl or alkyl substituents are rather soluble in water, whereas the introduction of substituents decreases the water solubility to such an extent that the usefulness of the compounds in aqueous media is restricted . Polarity is also observed for some derivatives: 2,4‐thiazolidinedione ( 1A ) shows a dipole moment of 2.03 D; rhodanine ( 1B ): 2.20 D; and 3‐ethylrhodanine ( 1C ): 1.75 D. …”

Section: Physical Properties and Stereochemistrymentioning

confidence: 99%

Thiazolidinones: Synthesis, Reactivity, and Their Biological Applications

Nirwan

Chahal

Kakkar

2019

Journal of Heterocyclic Chem

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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.

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Section: Physical Properties and Stereochemistrymentioning

confidence: 99%

Thiazolidinones: Synthesis, Reactivity, and Their Biological Applications

Nirwan

Chahal

Kakkar

2019

Journal of Heterocyclic Chem

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“…3-Phenethyl-2-thioxothiazolidin-4-one 6 was synthesized by modification of a literature procedure. 21 Phenylethylamine 5 was treated with CS 2 in diethyl ether at 0-5 °C followed by treatment with chloroacetic acid under reflux for 1 h to give 3-phenethyl-2-thioxothiazolidin-4-one 6 in 56% yield (Scheme 5).…”

Section: Chemistrymentioning

confidence: 99%

Design, Synthesis, and Structure−Activity Relationship of a Novel Series of 2-Aryl 5-(4-Oxo-3-phenethyl-2-thioxothiazolidinylidenemethyl)furans as HIV-1 Entry Inhibitors

et al. 2009

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We previously identified two small molecules targeting the HIV-1 gp41, N-(4-carboxy-3-hydroxy) phenyl-2,5-dimethylpyrrole 12 (NB-2) and N-(3-carboxy-4-chloro) phenylpyrrole 13 (NB-64) that inhibit HIV-1 infection at low μM level. Based on molecular docking analysis, we designed a series of 2-aryl 5-(4-oxo-3-phenethyl-2-thioxothiazolidinylidenemethyl)furans. Compared with 12 and 13, these compounds have bigger molecular size (437-515 Da) and could occupy more space in the deep hydrophobic pocket on the gp41 NHR-trimer. Fifteen 2-aryl 5-(4-oxo-3-phenethyl-2-thioxothiazolidinylidenemethyl)furans (11a-o) were synthesized by Suzuki-Miyaura cross coupling, followed by a Knoevenagel condensation and tested for their anti-HIV-1activity and cytotoxicity on MT-2 cells. We found that all 15 compounds had improved anti-HIV-1 activity and 3 of them (11a, 11b, and 11d) exhibited inhibitory activity against replication of HIV-1 IIIB and 94UG103 at <100 nM range, more than 20-fold more potent than 12 and 13, suggesting that these compounds can serve as leads for development of novel small molecule HIV fusion inhibitors.

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“…(23,303,437). With the exception of phenylsulfonic acid groups (7), the introduction of substituents decreases the water solubility to such an extent that the usefulness of the compounds in aqueous solution is restricted (103,341,394,548).…”

Section: -Thiazolidinonesmentioning

confidence: 99%