Synthesis and anticonvulsant activity of new N-Mannich bases derived from 5-cyclopropyl-5-phenyl- and 5-cyclopropyl-5-(4-chlorophenyl)-imidazolidine-2,4-diones

Byrtus, Hanna; Obniska, Jolanta; Czopek, Anna; Kamiński, Krzysztof; Pawłowski, Maciej

doi:10.1016/j.bmc.2011.08.017

Cited by 28 publications

(30 citation statements)

References 26 publications

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“…Several such derivatives (phenytoin, mephenythoin, norantoin, methetoin, ethotoin, fosphenytoin) are well-known anticonvulsive drugs [ 9 , 10 ]. Other 5-substituted hydantoins like 5,5-dithienylhydantoin, 5,5-dipyridylhydantoin, spirothiohydantoin, thiohydantoin, and dithiohydantoins also possess anticonvulsive activity [ 11 , 12 ]. Hydantoin derivatives can also be found as antiarrhythmics (azimilide), antimicrobial agents (nitrofurantoin), skeletal muscle relaxants (dantrolene), and nonsteroidal antiandrogens (nilutamide), while allantoin is used as a keratolytic, astringent, wound remedy, antacid, and antipsoriatic drug [ 10 ].…”

Section: Introductionmentioning

confidence: 99%

Bioactive Hydantoin Alkaloids from the Red Sea Marine Sponge Hemimycale arabica

2015

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In the course of our continuing efforts to identify bioactive secondary metabolites from Red Sea marine invertebrates, we have investigated the sponge Hemimycale arabica. The antimicrobial fraction of an organic extract of the sponge afforded two new hydantoin alkaloids, hemimycalins A and B (2 and 3), together with the previously reported compound (Z)-5-(4-hydroxybenzylidene)imidazolidine-2,4-dione (1). The structures of the compounds were determined by extensive 1D and 2D NMR (COSY, HSQC and HMBC) studies and high-resolution mass spectral determinations. Hemimycalins A (2) and B (3) represent the first examples of the natural N-alkylated hydantoins from the sponge Hemimycale arabica. Compounds 1–3 displayed variable antimicrobial activities against E. coli, S. aureus, and C. albicans. In addition, compound 1 displayed moderate antiproliferative activity against the human cervical carcinoma (HeLa) cell line. These findings provide further insight into the chemical diversity as well as the biological activity of this class of compounds.

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Section: Introductionmentioning

confidence: 99%

Bioactive Hydantoin Alkaloids from the Red Sea Marine Sponge Hemimycale arabica

2015

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“…phenytoin, it was more active in the anti-convulsion assays. Additionally compound 171 with ED50 of 26.06 mg/kg in a psychomotor seizure test (6-Hz) in mice showed comparable activity to a new generation anticonvulsant-levetiracetam [141]. …”

Section: The Imidazoline-24-dione Functional Groupmentioning

confidence: 93%

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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“…Byrtus et al synthesized Mannich derivatives of 5-cyclopropyl-5-phenyl-imidazolidine-2,4-dione. 66 However, the parent molecule exhibited better anticonvulsant activity than the corresponding Mannich derivatives.…”

Section: Synthesis Of Anticonvulsant Moleculesmentioning

confidence: 98%

Mannich reaction: A versatile and convenient approach to bioactive skeletons

Ganesan

2013

J Chem Sci

113

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This review gives an insight into the recent applications of Mannich reaction and its variants in the construction of bioactive molecules. Emphasis is given to the Mannich reaction that provides bioactive molecules and/or modifies the property of an existing bioactive molecule. The role of Mannich reaction in the construction of antimalarial, antitumour, antimicrobial, antitubercular, antiinflammatory and anticonvulsant molecules and also the significance of aminoalkyl Mannich side chain on the biological property of molecules is discussed here.

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Synthesis and anticonvulsant activity of new N-Mannich bases derived from 5-cyclopropyl-5-phenyl- and 5-cyclopropyl-5-(4-chlorophenyl)-imidazolidine-2,4-diones

Cited by 28 publications

References 26 publications

Bioactive Hydantoin Alkaloids from the Red Sea Marine Sponge Hemimycale arabica

Bioactive Hydantoin Alkaloids from the Red Sea Marine Sponge Hemimycale arabica

Current Research on Antiepileptic Compounds

Mannich reaction: A versatile and convenient approach to bioactive skeletons

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