Succinimides: Synthesis, properties and anticonvulsant activity

Banjac, Nebojša; Trišović, Nemanja; Valentić, Nataša V.; Ušćumlić, Gordana S.; Petrović, Slobodan

doi:10.2298/hemind110224030b

Cited by 9 publications

(8 citation statements)

References 32 publications

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“…In the literature, we have found information about the behaviour of aqueous solutions of SI in alkaline medium. It reveals the existence of a hydrolysis process of the SI with irreversible ring‐cleavage and formation of succinamic acid . The hydrolysis process is delayed until the pH values is above the p K a of succinimide .…”

Section: Results and Mechanismmentioning

confidence: 96%

“…All compounds studied in this paper are of the extensive interest in different fields of application, not only because of their direct application but also because they are part of structure of other more complex compounds conferring interesting properties for their application. [73][74][75][76][77][78] Consequently, it is quite probable that these compounds are in contact with chlorinated aqueous solutions, both in the human digestive system and the natural environment. Thus, the N-chlorination process shown in this paper may take place in both systems.…”

Section: Discussionmentioning

confidence: 99%

“…It reveals the existence of a hydrolysis process of the SI with irreversible ringcleavage and formation of succinamic acid. [8,44,45,[48][49][50] The hydrolysis process is delayed until the pH values is above the pK a of succinimide. [46] The specie formed, succinamic acid, can react with the ClO À to give an N-chloro compound (Scheme 3).…”

Section: Reaction Mechanism Of N-chlorosuccinimide Formationmentioning

confidence: 99%

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N-Chlorination rate of five-membered heterocyclic nitrogen compounds

Pastoriza

Antelo

Amoedo

et al. 2016

J. Phys. Org. Chem.

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aThe kinetics of N-chlorination reaction of pyrrolidine, pyrrolidone, succinimide, 5,5,-dimethyloxazolidine-2,4-dione, 5,5-dimethylhydantoin and 1-hydroximethyl-5,5-dimethylhydantoin with HOCl in aqueous solution were studied at 25°C, constant ionic strength and under isolation conditions in a wide pH range. The set of compounds studied in this paper is characterized by having different functional groups and the same cyclic structure, consisting of a five-member ring with a nitrogen atom in the ring, which is susceptible to be chlorinated. This series of compounds covers nine pK a units, and the kinetic studies allow us to know, like, the presence of an amino, amide or imide group modify the reactivity of nitrogenous compound.Experimental data were fitted to the first-order kinetic equation. All reactions were found to be of first order in both HOCl and nitrogenous compound concentration. Kinetics studies demonstrate that some of these compounds are hydrolyzed in alkaline medium. In each case, reaction mechanism in agreement with the experimental results is proposed. The results were compared with other compounds with similar cyclic structure (2-oxazolidinone and proline).

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Section: Results and Mechanismmentioning

confidence: 96%

Section: Discussionmentioning

confidence: 99%

Section: Reaction Mechanism Of N-chlorosuccinimide Formationmentioning

confidence: 99%

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N-Chlorination rate of five-membered heterocyclic nitrogen compounds

Pastoriza

Antelo

Amoedo

et al. 2016

J. Phys. Org. Chem.

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“…2 On the other hand, chromones are an important moiety, forming the nucleus of a class of heterocyclic natural products called flavanoids that occur naturally in fruits, vegetables, nuts, seeds, flowers, and bark. 3 They are an integral part of the human diet and have been reported to exhibit a wide range of biological effects.…”

mentioning

confidence: 99%

“…Succinimide-substructure-containing compounds show great pharmacological potential acting as enzyme inhibitors, analgesics, antimicrobial agents, anxiolytics, cytotoxic, anticonvulsants, antitumor drugs, and anti-Parkinson's agents. 2 On the other hand, chromones are an important moiety, forming the nucleus of a class of heterocyclic natural products called flavanoids that occur naturally in fruits, vegetables, nuts, seeds, flowers, and bark. 3 They are an integral part of the human diet and have been reported to exhibit a wide range of biological effects.…”

mentioning

confidence: 99%

Diastereoselective One-Pot Synthesis of Succinimides Bearing a Chromone Unit

Teimouri

Asnaashari

Moayedi

et al. 2014

Synlett

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In silico–in vitro estimation of lipophilicity and permeability association for succinimide derivatives using chromatographic anisotropic systems and parallel artificial membrane permeability assay

Vidović

Milošević

Pavlović

et al. 2022

Biomedical Chromatography

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Passive permeability is one of the key features that determine absorbability and one of the most studied properties in the early phases of drug development.Newly synthesized succinimide derivatives from two different series (1-aryl-3-methylsuccinimides and 1-aryl-3-ethyl-3-methylsuccinimides) with high biological potential have been subjected to estimation of their passive permeability and their association with (a) experimentally obtained anisotropic lipophilicity, (b) in silico-calculated lipophilicity and (c) in silico-predicted permeability and absorbability.Non-cellular-based parallel artificial membrane permeability assay was applied for quantifying their passive permeation, expressed as logP app . Passive permeation was governed by the lipophilicity of the analysed compounds, and anisotropic lipophilicity was related with statistically significant passive transcellular diffusion (r 2 = 0.614, P < 0.001). Moreover, experimentally determined passive permeability, logP app , was statistically significantly associated with both in silico-predicted absorption constant, k a (r 2 = 0.7886, P < 0.001), and human intestinal absorption (HIA) in percentage (r 2 = 0.484, P < 0.001), respectively. However, there was no statistically significant relationship between experimentally obtained permeability on non-cellular-based model and in silico-predicted Caco-2 permeability based on the predictions conducted on two different software. Based on the obtained results, anisotropic systems are promising surrogates for determining lipophilicity, except for compounds with acidic functional groups that are completely ionized under (pH = 7.4).

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Succinimides: Synthesis, properties and anticonvulsant activity

Cited by 9 publications

References 32 publications

N-Chlorination rate of five-membered heterocyclic nitrogen compounds

N-Chlorination rate of five-membered heterocyclic nitrogen compounds

Diastereoselective One-Pot Synthesis of Succinimides Bearing a Chromone Unit

In silico–in vitro estimation of lipophilicity and permeability association for succinimide derivatives using chromatographic anisotropic systems and parallel artificial membrane permeability assay

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