Synthesis of Some Azoles Incorporating a Sulfonamide Moiety as Anticonvulsant Agents

Farag, Awatef A.; Abd-Alrahman, Safaa N.; Ahmed, Gihan F.; Ammar, Ramy M.; Ammar, Yousry A.; Abbas, Samir Y.

doi:10.1002/ardp.201200014

Cited by 64 publications

(39 citation statements)

References 19 publications

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“…It is known that a great variety of reactants bearing the N-C-S fragment undergo cyclization on reaction with α-halocarbonyl compounds to afford thiazole, 2,3-dihydro-thiazole and thiazolidines moieties [23] which have been shown to exhibit local antitumor and antioxidant [24], antimicrobial [25], and antitumor activity [26]. Here, we describe a generally applicable extension of this synthetic approach; the base prompted reaction of the acidic methylene compound (1) with phenyl isothiocyanate in dry dimethylformamide at room temperature yields the non-isolable intermediate (3). The intermediate (3) undergoes in situ cyclization upon the reaction with equimolar amount of chloroacetyl chloride to give the corresponding ((E)-2-cyano-N-(naphthalene-1-yl)-2-(5-oxo-3-phenylthiazolidin-2-ylidene)acetamide) (4).…”

Section: Resultsmentioning

confidence: 99%

“…Here, we describe a generally applicable extension of this synthetic approach; the base prompted reaction of the acidic methylene compound (1) with phenyl isothiocyanate in dry dimethylformamide at room temperature yields the non-isolable intermediate (3). The intermediate (3) undergoes in situ cyclization upon the reaction with equimolar amount of chloroacetyl chloride to give the corresponding ((E)-2-cyano-N-(naphthalene-1-yl)-2-(5-oxo-3-phenylthiazolidin-2-ylidene)acetamide) (4). The IR spectrum of (4) showed an absorption peak at 1732 cm (4) showed singlet signal at δ 3.99 ppm corresponding to the methylene thiazolinone protons and D 2 O exchangeable singlet signal at δ 9.57 ppm because of NH.…”

Section: Resultsmentioning

confidence: 99%

“…To a solution of (11) (0.34 g, 1 mmol), containing few drops of piperidine, in (1:1) EtOH-DMF (20 mL), 2-(benzo[d] [1,3]dioxol-5-ylmethylene) malononitrile (15) (0.2 g, 1 mmol) was added. The reaction mixture was heated under reflux for 4 h; then left to cool at room temperature, the separated solid product was filtered off, dried, and recrystallized from EtOH to give compound (17 A solution of (11) (0.343 g, 1.0 mmol) in glacial acetic acid and acetic anhydride (15 mL) was heated under reflux for 3 h, then left to cool.…”

Section: Synthesis Of ((E)-2-((e)-4-(2-(1h-benzo[d]imidazol-2-yl) Hydmentioning

confidence: 99%

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Synthesis of Thiazolinone, Aminopyrazole, Pyrazolopyrimidine, and Pyrazolotriazine Derivatives Starting from 1‐Naphthyl‐2‐Cyanoacetamide

Fadda

Rabie

Etman

2016

Journal of Heterocyclic Chem

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Efficient and suitable methods for the synthesis of novel class of simple and fused heterocyclic compounds were prepared starting with 1-naphthyl-2-cyanoacetamide and commercially available reagents. The cyclocondensation of 1-naphthyl-2-cyanoacetamide with sulfanylacetic acid furnished phenylthiazolinone derivative. Stirring of the starting compound with PhNCS afforded thiocarbamoyl derivative which underwent heterocyclization with chloroacetyl chloride to give thiazolinone derivative. 5-Aminopyrazole derivative was prepared by following mild procedures via refluxing the last thiocarbamoyl with hydrazine hydrate. Different synthetic approaches were discussed to obtain the novel fused pyrazolo[1,5-a]pyrimidine, 4H-pyrazolo[3,4-d]pyrimidin-4-one moieties involving the reaction of the prepared 5-aminopyrazole with a) 1, 3-dielectrophilic centers (acetylacetone, acetoacetanilide), b) arylidines of malononitrile, and c) isothiocyanate derivatives. The action of iced sodium nitrite solution in acidic medium on the last 5-aminopyrazole gave pyrazolo [3,4-d][1,2,3]triazine. All novel structure were elucidated by different spectroscopic data (IR, MS,

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of ((E)-2-((e)-4-(2-(1h-benzo[d]imidazol-2-yl) Hydmentioning

confidence: 99%

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Synthesis of Thiazolinone, Aminopyrazole, Pyrazolopyrimidine, and Pyrazolotriazine Derivatives Starting from 1‐Naphthyl‐2‐Cyanoacetamide

Fadda

Rabie

Etman

2016

Journal of Heterocyclic Chem

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“…[12][13][14] These derivatives are still widely used today for the treatment of various bacterial, protozoal and fungal infections [15] and are the first effective chemotherapeutic agent used in safe therapeutic dosage ranges. [16] Based on the above mentioned observations and in continuation of our research program on the field of sulfonamide derivatives, [17][18][19][20][21] antimicrobial and antifungal agents, [22][23][24][25] we would like to report the synthesis of furochromone, benzofuran and furocoumarin derivatives containing sulfonamide moiety as a trial to obtain novel class of antibacterial and antifungal agents.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Furochromone, Benzofuran and Furocoumarin Derivatives Bearing Sulfonyl Moiety

Hessein¹,

El‐Sharief²,

Abbas³

et al. 2016

Croat. Chem. Acta

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New visnagin-9-sulfonamide derivatives 3 and 4a−c were synthesized through the reaction of visnagin-9-sulfonyl chloride 2 with amino compounds. Acetylation of compounds 4b and 4c gave the monoacetyl and diacetyl derivatives 5 and 6, respectively. Diazotization reaction of compound 4b afforded the corresponding benzotriazole derivative 8. Pyrazole and thiopyrimidine derivatives 9 and 10 were obtained via the opening of pyrone ring upon reaction of compound 3 with hydrazine hydrate and thiourea, respectively. In addition, hydrolysis of compound 3 with potassium hydroxide furnished the visnaginone derivative 11 which used as starting material for synthesize benzofuran derivatives 12−14 and bergaptene derivatives 15−17. The synthesized compounds were tested for antimicrobial activity. Furochromone derivatives 3, 4a−c, 5, 6 and 8 (visnagin-9-sulfonamide derivatives) demonstrate moderate antibacterial and antifungal activities compared with the antibacterial and antifungal activites of the standard drugs. Benzofuran derivatives 11−14 (visnaginone derivatives) showed the lowest antimicrobial activity among all the compounds investigated in this study. Furocoumarin derivatives 15a,b, 16 and 17 (furobenzopyransulfonamide [bergaptensulfonamides]) are moderately active against all the tested strains.

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“…Compound 46 obviously showed anticonvulsant activity with no tonic stretching stage and protected all the animals tested ( Figure 1) [45]. …”

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confidence: 96%

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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Synthesis of Some Azoles Incorporating a Sulfonamide Moiety as Anticonvulsant Agents

Cited by 64 publications

References 19 publications

Synthesis of Thiazolinone, Aminopyrazole, Pyrazolopyrimidine, and Pyrazolotriazine Derivatives Starting from 1‐Naphthyl‐2‐Cyanoacetamide

Synthesis of Thiazolinone, Aminopyrazole, Pyrazolopyrimidine, and Pyrazolotriazine Derivatives Starting from 1‐Naphthyl‐2‐Cyanoacetamide

Synthesis and Antimicrobial Activity of Furochromone, Benzofuran and Furocoumarin Derivatives Bearing Sulfonyl Moiety

Current Research on Antiepileptic Compounds

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