2-Aryl-3-(2-morpholinoethyl)thiazolidin-4-ones: Synthesis, anti-inflammatory in vivo, cytotoxicity in vitro and molecular docking studies

Gouvêa, Daniela P.; Vasconcellos, Flávia Aleixo; Berwaldt, Gabriele dos Anjos; Neto, Amilton Clair Pinto Seixas; Fischer, Gerferson; Sakata, Renata Parruca; Almeida, Wanda P.; Cúnico, Wilson

doi:10.1016/j.ejmech.2016.04.028

Cited by 41 publications

(8 citation statements)

References 33 publications

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“…In this work, the compounds were synthesized using the thermal heating methodology and the reaction conditions previously described by our research group 23 , however, all reactions were monitored by TLC and/or GC analysis. Novel nineteen 1,3-benzothiazin-4-ones ( 5Aa–g , 5Ba–f and 5Ca–f ) were synthesized from one-pot reactions between different amines 1A–C , different aldehydes 2a–g and thiosalicylic acid 4 ( Scheme 1 ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and biological evaluation of benzothiazin-4-ones: a possible new class of acetylcholinesterase inhibitors

Berwaldt

Gouvêa

Silva

et al. 2018

Journal of Enzyme Inhibition and Medicinal Chemistry

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A series of nineteen benzothiazin-4-ones from N-(3-aminopropyl) piperidine, 4-(2-aminoethyl)morpholine or 1-(2-aminoethyl)piperidine, aliphatic or aromatic aldehyde and thiosalicylic acid, were synthesized in good yields by multicomponent one-pot reactions. The solvent was toluene and this efficient procedure afforded the desired heterocycles in 5 h. Identification and characterization were achieved by NMR and GC–MS techniques. In vitro AChE activities of all compounds were evaluated in cerebral cortex and hippocampus of rats and in general, the results in cortex were more promising than hippocampus. The benzothiazinone 5Bd showed the best AChE inhibition activity IC50 8.48 μM (cortex) and IC50 39.80 μM (hippocampus). The cytotoxicity of seven compounds in MCR-5 human fibroblast cell by SRB test in 24 h were evaluated and 5Bd suggest preliminary safety, showing no cytotoxicity at 100 µM. Finally, these important findings could be a starting point for the development of new AChE inhibitors agents and will provide the basis for new studies.

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Section: Resultsmentioning

confidence: 99%

Synthesis and biological evaluation of benzothiazin-4-ones: a possible new class of acetylcholinesterase inhibitors

Berwaldt

Gouvêa

Silva

et al. 2018

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…The 1,3-thiazolidin-4-one derivatives are very important core structures of many heterocyclic compounds. Thiazolidinone and its analogues have outstanding biological activity, they are reported as antiinflammatory [15], antimicrobial [16], antidiabetic [17], anticancer [18], antioxidants [19]. On the other hand, thiazole is a well-known heterocyclic aromatic compound containing sulphur and nitrogen atoms at positions 1 and 3 of its five-member ring, respectively [20].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Thiazolidinones and Thiazoles in Indole Series

Vanelle

Khanoussi

Benmohammed

et al. 2023

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Recent findings confirm that thiosemicarbazones and thiazoles offer a wide range of biological properties. We report here the synthesis of two series of highly functionalized thiazole-derived compounds from the reactions of various indole-derived thiosemicarbazones with diethyl acetylenedicarboxylate and 4-bromophenacyl bromide. As a result, a series of new derivatives of thiosemicarbazone, thiazolidinone, and thiazole bearing an indole moiety was synthesized and developed in good yields.

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“…Numerous heterocyclic compounds containing nitrogen, sulfur, and oxygen heteroatoms have attracted the attention of chemists over the years because of their biological properties. In particular, the thiazolidin-4-ones, a privileged pharmacophore possesses an array of biological activities including anti-inflammatory [ 9 ], antimicrobial [ 10 ], antibiofilm [ 11 ], antiparasitic [ 12 ], anticancer [ 13 ], anti-viral [ 14 ], antidiabetic [ 15 ], antiarthritic [ 16 ], FSH agonist [ 17 ], JNK stimulating phosphatase-1 (JSP-1) [ 18 ], CNS-penetrant [ 19 ], CDK1/Cyclin B inhibition [ 20 ], COX-2 inhibitor [ 21 ] and hypoglycemia [ 22 ] properties. In the last few years, Kucukguzel et al developed substituted 4-thiazolidinones and among them compounds 1 and 4 exhibited excellent antitubercular activity with 90% and 98% inhibitions at 6.25 µg/mL, respectively [ 23 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Sulfamethaoxazole 4-Thiazolidinone Hybrids and Their Biological Evaluation

et al. 2020

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A search for potent antitubercular agents prompted us to design and synthesize sulfamethaoxazole incorporated 4-thiazolidinone hybrids (7a–l) by using a cyclocondensation reaction between 4-amino-N-(5-methylisoxazol-3-yl)benzenesulfonamide (4), aryl aldehyde (5a–l), and mercapto acetic acid (6) resulting in good to excellent yields. All the newly synthesized 4-thiazolidinone derivatives were screened for their in vitro antitubercular activity against M. Bovis BCG and M. tuberculosis H37Ra (MTB) strains. The compounds 7d, 7g, 7i, 7k, and 7l revealed promising antimycobacterial activity against M. Bovis and MTB strains with IC90 values in the range of 0.058–0.22 and 0.43–5.31 µg/mL, respectively. The most active compounds were also evaluated for their cytotoxicity against MCF-7, HCT 116, and A549 cell lines and were found to be non-cytotoxic. Moreover, the synthesized compounds were also analyzed for ADME (absorption, distribution, metabolism, and excretion) properties and showed potential as good oral drug candidates.

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2-Aryl-3-(2-morpholinoethyl)thiazolidin-4-ones: Synthesis, anti-inflammatory in vivo, cytotoxicity in vitro and molecular docking studies

Cited by 41 publications

References 33 publications

Synthesis and biological evaluation of benzothiazin-4-ones: a possible new class of acetylcholinesterase inhibitors

Synthesis and biological evaluation of benzothiazin-4-ones: a possible new class of acetylcholinesterase inhibitors

Synthesis of New Thiazolidinones and Thiazoles in Indole Series

Synthesis of Novel Sulfamethaoxazole 4-Thiazolidinone Hybrids and Their Biological Evaluation

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