Synthesis of novel thiazolidinic-phthalimide derivatives evaluated as new multi-target antiepileptic agents

Oliveira, Maria C.; Viana, Douglas Carvalho Francisco; Silva, Anderson A.; Pereira, Michelly Cristiny; Duarte, Filipe S.; Pitta, M. G. R.; Pitta, Ivan R.

doi:10.1016/j.bioorg.2021.105548

Cited by 9 publications

(7 citation statements)

References 44 publications

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“…2-(1,3-Dioxoisoindolin-2-yl)acetohydrazide ( 1) is used as precursor to synthesize a panel of new efficient compounds such as 1,2,4-triazole, 1,3,4thiadiazole, pyridazinetrione and another thiazolidine-2,4-dione, benzo[e] [1,3]thiazine and quinazolinedione ring systems. Compound 1 reacted with carbon disulfide in ethanolic potassium hydroxide solution at reflux temperature to compound 2 that reacted in DMF with hydrazine hydrate in absolute ethanol at reflux temperature to give compound 3 [26](Scheme 1).…”

Section: Scheme1mentioning

confidence: 99%

“…Experimental). 2-(1,3-Dioxoisoindolin-2-yl)acetyl azide (9) as starting material is used in reaction with thioglycolic acid, thiosalicylic acid, or anthranilic acid to afford thiazolidine-2,4-dione derivative 15, benzo[e] [1,3]thiazine derivative 16, and quinazoline-2,4(1H,3H)-dione derivative respectively (Scheme 4). [36]Structures of compounds 15-17 were elucidated according to their elemental and spectroscopic analyses (cf.…”

Section: Figure 1: Mechanism Of Azide Formation From Hydrazidesmentioning

confidence: 99%

“…Derivatives of phthalimide and thiazolidinone have the potential to be antimicrobial antimycobacterial, anti-inflammatory agents, analgesic, anticonvulsant, and anticancer activities. [1][2][3] Thiazolidinone scaffold is a versatile substance that can be found in a variety of clinically useful medications. [4,5] These phthalimide and thiazolidinone derivatives have varied biological applications such as antimicrobial activity antimalarial activity, anticancer activity and antiarrhythmic activity.…”

Section: Introductionmentioning

confidence: 99%

“…Compounds containing pyrimidine ring system are pivotal derivatives that have a wide efficiency of pharmaceutical and medicinal activities such as antibacterial, anticancer, anxiolytic, antiviral, antioxidant, and antidepressant activities [19][20][21][22][23][24][25]. According to above survey, the objective in this work is to synthesize a series of phthalimide derivatives containing a various heterocyclic rings such as thiazolidinone ring, triazole, benzo[e] [1,3]thiazine and another, and tested antibacterial activity of these novel derivatives which expected to possess a high biological activity.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Reactions, and Antimicrobial Evaluation of 2-(1,3-dioxoisoindolin-2-yl)acetohydrazide derivatives

2022

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New 2-(1,3-dioxoisoindolin-2-yl)acetohydrazide derivatives were synthesized, characterized and evaluated as antimicrobial agents. Phathalic anhydride was reacted with aminoacetoactate to afford phthalimide derivative which reacted with hydrazine hydrate to give New 2-(1,3-dioxoisoindolin-2-yl)acetohydrazide derivative 1. Compound 1 is used as precursor to synthesize various derivatives depending on types of reactants. Spectroscopic and analytical measurements are used to confirm structures of new products. Antimicrobial evaluation of new derivatives were done.

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Section: Scheme1mentioning

confidence: 99%

Section: Figure 1: Mechanism Of Azide Formation From Hydrazidesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, Reactions, and Antimicrobial Evaluation of 2-(1,3-dioxoisoindolin-2-yl)acetohydrazide derivatives

2022

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“…The most potent derivative (125) (Figure9) reduced proinflammatory cytokine levels of IL-17 and interferon (IFN)-γ and demonstrated promising latency times with values of <80 s at three different concentrations (100, 300, and 600 mg/kg) in a PTZ-induced seizure model. In vivo assay revealed that 125 is nontoxic, and molecular studies suggested a possible interaction with the GABAA receptors(De Oliveira et al, 2022).Human carbonic anhydrases (hCAs) are a family of zinccontaining metalloenzymes that have been identified as potential F I G U R E 8 Phthalimide derivatives discovered for Alzheimer's disease treatment.…”

mentioning

confidence: 99%

Phthalimide as a versatile pharmacophore scaffold: Unlocking its diverse biological activities

Fernandes

Lopes

Santos

et al. 2023

Drug Development Research

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Phthalimide, a pharmacophore exhibiting diverse biological activities, holds a prominent position in medicinal chemistry. In recent decades, numerous derivatives of phthalimide have been synthesized and extensively studied for their therapeutic potential across a wide range of health conditions. This comprehensive review highlights the latest developments in medicinal chemistry, specifically focusing on phthalimide‐based compounds that have emerged within the last decade. These compounds showcase promising biological activities, including anti‐inflammatory, anti‐Alzheimer, antiepileptic, antischizophrenia, antiplatelet, anticancer, antibacterial, antifungal, antimycobacterial, antiparasitic, anthelmintic, antiviral, and antidiabetic properties. The physicochemical profiles of the phthalimide derivatives were carefully analyzed using the online platform pkCSM, revealing the remarkable versatility of this scaffold. Therefore, this review emphasizes the potential of phthalimide as a valuable scaffold for the development of novel therapeutic agents, providing avenues for the exploration and design of new compounds.

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Chemistry and Applications of Functionalized 2,4‐Thiazolidinediones

et al. 2023

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Thiazolidinedione (TZD) is one of the privileged heterocyclic rings and has shown many biological applications in medicinal chemistry and drug discovery. This review covers the synthetic approaches of TZD and its derivatives, different synthetic techniques for affording the desired regioselectivity and stereoselectivity, and the techniques that would enhance reaction conditions such as microwave, one‐pot, or ultrasound synthesis. It focuses on synthetic challenges of glitazones and the transformation of other heterocycles to TZD. Moreover, the chemical and biological behavior of TZD through the substitution in the N3 position, modification of the C5 position, annealing in complex heterocyclic systems, and hybridization with other pharmacologically attractive moieties are discussed. All reactions mentioned are provided as possible with different reaction conditions, mechanisms, derivatives scope, yield and clarified by applications of such reactions in the construction of potential medicinal agents. The review also answers questions about rapid racemization of glitazones, their toxicity, considering TZD as pan‐assay interference compounds (PAINS) or not, and the influence of saturation of 5‐position of TZD in their biological activities. This review is a comprehensive guide to make informed decisions for construction of TZD derivatives with biological potentials.

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Synthesis of novel thiazolidinic-phthalimide derivatives evaluated as new multi-target antiepileptic agents

Cited by 9 publications

References 44 publications

Synthesis, Reactions, and Antimicrobial Evaluation of 2-(1,3-dioxoisoindolin-2-yl)acetohydrazide derivatives

Synthesis, Reactions, and Antimicrobial Evaluation of 2-(1,3-dioxoisoindolin-2-yl)acetohydrazide derivatives

Phthalimide as a versatile pharmacophore scaffold: Unlocking its diverse biological activities

Chemistry and Applications of Functionalized 2,4‐Thiazolidinediones

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