Synthesis and Pharmacological Investigation of 2‐(4‐Dimethylaminophenyl)‐3,5‐disubstituted thiazolidin‐4‐ones as Anticonvulsants

Senthilraja, M.; Alagarsamy, V.

doi:10.1002/ardp.201200126

Cited by 6 publications

(3 citation statements)

References 15 publications

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“…The title compounds were investigated for their anticonvulsant activities, among the test compounds, compound 244 emerged as the most active compound of the series and as moderately more potent than the reference standard diazepam ( Figure 13) [182].…”

Section: Lee Et Al Prepared 13 Derivatives Of N-(biphenyl-4′-yl)metmentioning

confidence: 99%

Current Research on Antiepileptic Compounds

2015

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Epilepsy affects about 1% of the world's population. Due to the fact all antiepileptic drugs (AEDs) have some undesirable side effects and about 30% of epileptic patients are not seizure-free with the existing AEDs, there is still an urgent need for the development of more effective and safer AEDs. Based on our research work on antiepileptic compounds and other references in recent years, this review covers the reported work on antiepileptic compounds which are classified according to their structures. This review summarized 244 significant anticonvulsant compounds which are classified by functional groups according to the animal model data, although there are some limitations in the data. This review highlights the properties of new compounds endowed with promising antiepileptic properties, which may be proven to be more effective and selective, and possibly free of unwanted side effects. The reviewed compounds represent an interesting possibility to overcome refractory seizures and to reduce the percentage of patients with a poor response to drug therapy.

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Section: Lee Et Al Prepared 13 Derivatives Of N-(biphenyl-4′-yl)metmentioning

confidence: 99%

Current Research on Antiepileptic Compounds

2015

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“…4-Thiazolidinones are a known class of drug-like molecules and improved drugs with a broad spectrum of biological effects [10,11], including anticonvulsant [12,13]. Thiazolidinone frame is considered as cyclic mimetic of thiosemicarbazides and thioureas as well as (bio)isoster of hidantoin (imidazolidine-2,4-dione) [11]-approved scaffolds of known anticonvulsants and privileged (sub)structures for new anticonvulsants design [14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Thiazole-Bearing 4-Thiazolidinones as New Anticonvulsant Agents

et al. 2020

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Here, we describe the synthesis and anticonvulsant activity of thiazole-bearing hybrids based on 2-imino-4-thiazolidinone and 2,4-dioxothiazolidine-5-carboxylic acid cores. The structure of target compounds was based on the following: (i) A combination of two thiazole cores; (ii) similarity to ralitolin’s structure; (iii) the compliance with structural requirements for the new anticonvulsants. Target compounds were synthesized via known approaches based on Knoenavegel reaction, alkylation reaction, and one-pot three-component reaction. Anticonvulsant properties of compounds were evaluated in two different models—pentylenetetrazole-induced seizures and maximal electroshock seizure tests. Among the tested compounds 5Z-(3-nitrobenzylidene)-2-(thiazol-2-ylimino)-thiazolidin-4-one Ib, 2-[2,4-dioxo-5-(thiazol-2- ylcarbamoylmethyl)-thiazolidin-3-yl]-N-(2-trifluoromethylphenyl)acetamide IId and (2,4-dioxo-5- (thiazol-2-ylcarbamoylmethylene)-thiazolidin-3-yl)acetic acid ethyl ester IIj showed excellent anticonvulsant activity in both models. The directions of compounds modification based on SAR aspects were discussed. The results of the study provide a basis for further study of the anticonvulsant properties of selected thiazole-thiazolidinones.

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“…Many recent research studies have focused on thiazolidine-4-one heterocycle, due to the role it plays in the synthesis [ 10 ] of new derivatives which showed significant biological activity as antidiabetic [ 11 , 12 ], antioxidant [ 13 – 15 ], anticonvulsant [ 16 ], anticancer [ 17 ], anti-inflammatory, analgesic [ 18 ], antimicrobial, antifungal [ 19 ], antiviral [ 20 ], antihypertensive, antiarrhythmic [ 21 ], anti-mycobacterial [ 22 ] and antiparasitic [ 23 ] effect. Moreover, the thiazolidinediones developed from this scaffold are important drugs used in treatment of diabetes mellitus type 2.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of the new 1,3-dimethylxanthine derivatives with thiazolidine-4-one scaffold

Constantin

Lupașcu

Apotrosoaei

et al. 2017

Chemistry Central Journal

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BackgroundThe xanthine structure has proved to be an important scaffold in the process of developing a wide variety of biologically active molecules such as bronchodilator, hypoglycemiant, anticancer and anti-inflammatory agents. It is known that hyperglycemia generates reactive oxygen species which are involved in the progression of diabetes mellitus and its complications. Therefore, the development of new compounds with antioxidant activity could be an important therapeutic strategy against this metabolic syndrome.ResultsNew thiazolidine-4-one derivatives with xanthine structure have been synthetized as potential antidiabetic drugs. The structure of the synthesized compounds was confirmed by using spectral methods (FT-IR, 1H-NMR, 13C-NMR, 19F-NMR, HRMS). Their antioxidant activity was evaluated using in vitro assays: DPPH and ABTS radical scavenging ability and phosphomolybdenum reducing antioxidant power assay. The developed compounds showed improved antioxidant effects in comparison to the parent compound, theophylline. In the case of both series, the intermediate (5a–k) and final compounds (6a–k), the aromatic substitution, especially in para position with halogens (fluoro, chloro), methyl and methoxy groups, was associated with an increase of the antioxidant effects.ConclusionsFor several thiazolidine-4-one derivatives the antioxidant effect of was superior to that of their corresponding hydrazone derivatives. The most active compound was 6f which registered the highest radical scavenging activity.Graphical abstractDesign and synthesis of new thiazolidine-4-one derivatives. Electronic supplementary materialThe online version of this article (doi:10.1186/s13065-017-0241-0) contains supplementary material, which is available to authorized users.

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Synthesis and Pharmacological Investigation of 2‐(4‐Dimethylaminophenyl)‐3,5‐disubstituted thiazolidin‐4‐ones as Anticonvulsants

Cited by 6 publications

References 15 publications

Current Research on Antiepileptic Compounds

Current Research on Antiepileptic Compounds

Thiazole-Bearing 4-Thiazolidinones as New Anticonvulsant Agents

Synthesis and biological evaluation of the new 1,3-dimethylxanthine derivatives with thiazolidine-4-one scaffold

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