5,5-Disubstituted hydantoins: syntheses and anti-HIV activity

Comber, Rob; Reynolds, Robert C.; Friedrich, Joyce D.; Manguikian, Roupen A.; Buckheit, Robert W.; Truss, Jackie W.; Shannon, William M.; Secrist, John A.

doi:10.1021/jm00097a014

Cited by 68 publications

(36 citation statements)

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“…Their substitution products have also been found a number of other pharmacological properties such as antitumor, anti-HIV and antibacterial activities [135][136][137].…”

Section: The Imidazoline-24-dione Functional Groupmentioning

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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“…Their substitution products have also been found a number of other pharmacological properties such as antitumor, anti-HIV and antibacterial activities [135][136][137].…”

Section: The Imidazoline-24-dione Functional Groupmentioning

confidence: 99%

Current Research on Antiepileptic Compounds

2015

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“…Dried over Na 2 SO 4 and concentrated in vacuo to get pure product 7. General procedure for the synthesis of triazaspiro sulfonamides (8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22) The reactants such as 3-[ (2,4-dioxo-1,3,8-triazaspiro[4.6]undec-3-yl)methyl]benzonitrile 7 (100 mg 0.33 mmol), triethylamine (50.88 mg, 0.50 mmol), and sulfonyl chloride (0.37 mmol) in dichloromethane (4 mL) were mixed and stirred at room temperature for 16 h. After completion of the reaction (TLC), it was quenched with saturated sodium bicarbonate solution, extracted with dichloromethane (3 Â 4 mL), dried over Na 2 SO 4 and concentrated in vacuo to give the crude product which was purified by column chromatography on silica employing dichloromethane/methanol (9:1) as an eluent to obtain pure white solid (8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22).…”

Section: Synthesis Of Tert-butyl 4-oxoazepane-1-carboxylate (4)mentioning

confidence: 99%

“…Depending on the nature of substitution on the hydantoin ring, a wide range of other pharmacological properties, e.g., antihypertensive [11], herbicidal [12], antitumor [13], anti-HIV [14], antibacterial [15] and antiviral [16] activities, have also been identified.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of 3‐[(2,4‐Dioxo‐1,3,8‐triazaspiro[4.6]undec‐3‐yl)methyl]benzonitrile Derivatives as Potential Anticonvulsants

Madaiah

Prashanth

Revanasiddappa

et al. 2013

Archiv der Pharmazie

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New 3- [(2,4-dioxo-1,3,8-triazaspiro[4.6]undec-3-yl)methyl]benzonitrile derivatives 8-37 were synthesized and their pharmacological activities were determined with the objective to better understand their structure-activity relationship (SAR) for anticonvulsant activity. All the compounds were evaluated for their possible anticonvulsant activity by maximal electroshock seizure (MES) and pentylenetetrazole (PTZ) test. Compounds 11, 18, 31, and 32 showed significant and protective effect on seizure, when compared with the standard drug valproate. The same compounds were found to exhibit advanced anticonvulsant activity as well as lower neurotoxicity than the reference drug. From this study, it is quite apparent that there are at least three parameters for the activity of anticonvulsant drugs, that is, a lipophilic domain, a hydrophobic center, and a twoelectron donor.

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“…6 Phenytoin 1 (5,5-diphenylhydantoin, DPH) is one of the best known derivatives of hydantoin. This heterocycle is a useful pharmacological compound and extensively used as an anticonvulsant agent, 7 treatment of epileptic seizures, 8,9 epidermolysis bullosa, 10 inflammatory conditions, case of anticonvulsant activity of DPH, it has been established that the site of the action of this compound is the neuronal voltage-sensitive sodium channel, though no more information about the location and nature of this site has been reported. 14,15 In contrast to the many examples of the Michael addition amines on different unsaturated systems, there are only a few reports on the amides and imides Michael reaction (due to the low reactivity of them) with these systems.…”

Section: Introductionmentioning

confidence: 99%

Solvent-free highly regioselective Michael addition of phenytoin to α,β-unsaturated esters in the presence of TBAB under ultrasound irradiation

Imanzadeh¹,

Rezaee-Gatar²

2015

Arkivoc

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The highly regioselective C-N bond formation between phenytoin and acrylic/fumaric esters was accomplished. Solvent-free media Michael addition of phenytoin to acrylic esters led to the selective synthesis of N3-substituted phenytoins (as mono-Michael adducts) in the presence of tetrabutylammonium bromide (TBAB) and potassium carbonate under ultrasonic irradiation conditions at room temperature. These reactions produced N1,N3-disubstituted phenytoins (as bis-Michael adducts) at 70 ºC. Surprisingly, the addition of phenytoin to fumaric esters, instead of acrylic esters, selectively provided only N3-substituted phenytoins at both room temperature and 70 ºC under the same conditions.

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5,5-Disubstituted hydantoins: syntheses and anti-HIV activity

Cited by 68 publications

References 0 publications

Current Research on Antiepileptic Compounds

Current Research on Antiepileptic Compounds

Synthesis and Evaluation of 3‐[(2,4‐Dioxo‐1,3,8‐triazaspiro[4.6]undec‐3‐yl)methyl]benzonitrile Derivatives as Potential Anticonvulsants

Solvent-free highly regioselective Michael addition of phenytoin to α,β-unsaturated esters in the presence of TBAB under ultrasound irradiation

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