Novel Calcium Antagonists with Both Calcium Overload Inhibition and Antioxidant Activity. 1. 2-(3,5-Di-<i>tert-</i>butyl-4-hydroxyphenyl)-3-(aminopropyl)thiazolidinones

Kato, Tatsuya; Ozaki, Tomokazu; Tamura, Kazuhiko; Suzuki, Yoshiyuki; Akima, Michitaka; Ohi, Nobuhiro

doi:10.1021/jm980335f

Cited by 35 publications

(17 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Panetta et al reported the anti-inflammatory effect of several 4-thiazolidinones [7]. A number of thiazolidinones have been shown to possess antioxidant and calcium overload inhibiting activities [8]. Suitably substituted thiazolidinones have been reported to reduce serum cholesterol, triglyceride, and glucose levels in our laboratory [9, 10].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Preclinical Evaluation of New Thiazolidin-4-ones Substituted with p-Chlorophenoxy Acetic Acid and Clofibric Acid against Insulin Resistance and Metabolic Disorder

Gowdra

Mudgal

Bansal

et al. 2014

BioMed Research International

View full text Add to dashboard Cite

We synthesized twenty thiazolidin-4-one derivatives, which were then characterized by standard chromatographic and spectroscopic methods. From the in vitro glucose uptake assay, two compounds behaved as insulin sensitizers, where they enhanced glucose uptake in isolated rat diaphragm. In high-carbohydrate diet-induced insulin resistant mice, these two thiazolidin-4-ones attenuated hyperglycemia, hyperinsulinemia, hypertriglyceridemia, hypercholesterolemia, and glucose intolerance. They raised the plasma leptin but did not reverse the diabetes-induced hypoadiponectinemia. Additionally, compound 3a reduced adiposity. The test compounds were also able to reverse the disturbed liver antioxidant milieu. To conclude, these two novel thiazolidin-4-ones modulated multiple mechanisms involved in metabolic disorders, reversing insulin resistance and thus preventing the development of type-2 diabetes.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Preclinical Evaluation of New Thiazolidin-4-ones Substituted with p-Chlorophenoxy Acetic Acid and Clofibric Acid against Insulin Resistance and Metabolic Disorder

Gowdra

Mudgal

Bansal

et al. 2014

BioMed Research International

View full text Add to dashboard Cite

show abstract

“…The presence of N-C-S linkage in the compounds has been shown to have hypnotic, 2 anti-cancer, 3 cardiovascular, 4 antioxidant, 5 anti-inflamatory, 6 antitubercular, 7 antihistaminic, 8 antimicrobial, 9 anticonvulsant, 10 antiviral and anti-HIV 11 acivities. Besides, carbazole, pyrazole and tiazole skeletons constitute the structural core element of many natural and synthesized products.…”

Section: Introductionmentioning

confidence: 99%

Highly Efficient and Chemoselective Synthetic Route to de Thiazolidinones via a Microwave Assisted, Three Component Reaction

Ocampo

Koll

D’Accorso

et al. 2014

Proceedings of the 18th International Electronic Conference on Synthetic Organic Chemistry

View full text Add to dashboard Cite

show abstract

“…Therefore, it is no surprise that BHT has been modified to prepare a series of new antioxidants having new medicinal properties in the pharmaceutical industry [ 12 , 22 , 23 ]. Recently, qualitative SARS and rational-design strategies for antioxidants have been used to combine multiple functions; including various multiple antioxidant properties such as radical-scavenging ability and diversified pharmacological activities to offer hybrid compounds, which can exert multiple pharmacological functions through one molecular framework [ 24 , 25 , 26 ].…”

Section: Introductionmentioning

confidence: 99%

Butylated Hydroxytoluene Analogs: Synthesis and Evaluation of Their Multipotent Antioxidant Activities

et al. 2012

View full text Add to dashboard Cite

A computer-aided predictions of antioxidant activities were performed with the Prediction Activity Spectra of Substances (PASS) program. Antioxidant activity of compounds 1, 3, 4 and 5 were studied using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and lipid peroxidation assays to verify the predictions obtained by the PASS program. Compounds 3 and 5 showed more inhibition of DPPH stable free radical at 10−4 M than the well-known standard antioxidant, butylated hydroxytoluene (BHT). Compound 5 exhibited promising in vitro inhibition of Fe2+-induced lipid peroxidation of the essential egg yolk as a lipid-rich medium (83.99%, IC50 16.07 ± 3.51 µM/mL) compared to α-tocopherol (α-TOH, 84.6%, IC50 5.6 ± 1.09 µM/mL). The parameters for drug-likeness of these BHT analogues were also evaluated according to the Lipinski’s “rule-of-five” (RO5). All the BHT analogues were found to violate one of the Lipinski’s parameters (LogP > 5), even though they have been found to be soluble in protic solvents. The predictive polar surface area (PSA) and absorption percent (% ABS) data allow us to conclude that they could have a good capacity for penetrating cell membranes. Therefore, one can propose these new multipotent antioxidants (MPAOs) as potential antioxidants for tackling oxidative stress and lipid peroxidation processes.

show abstract

Novel Calcium Antagonists with Both Calcium Overload Inhibition and Antioxidant Activity. 1. 2-(3,5-Di-tert-butyl-4-hydroxyphenyl)-3-(aminopropyl)thiazolidinones

Cited by 35 publications

References 31 publications

Synthesis, Characterization, and Preclinical Evaluation of New Thiazolidin-4-ones Substituted with p-Chlorophenoxy Acetic Acid and Clofibric Acid against Insulin Resistance and Metabolic Disorder

Synthesis, Characterization, and Preclinical Evaluation of New Thiazolidin-4-ones Substituted with p-Chlorophenoxy Acetic Acid and Clofibric Acid against Insulin Resistance and Metabolic Disorder

Highly Efficient and Chemoselective Synthetic Route to de Thiazolidinones via a Microwave Assisted, Three Component Reaction

Butylated Hydroxytoluene Analogs: Synthesis and Evaluation of Their Multipotent Antioxidant Activities

Contact Info

Product

Resources

About