Hydantoins as antitumor agents

Rodgers, Thomas R.; Lamontagne, M. P.; Markovac, A.; Ash, A. B.

doi:10.1021/jm00214a031

Cited by 62 publications

(37 citation statements)

References 3 publications

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“…This imidazolidine structure is present in a wide range of biologically active compounds with important applications in medicinal fields, such as antitumor [1] and anti-arrhythmic agents [2], anti-cancer drugs [3] having also agrochemical applications (bactericides and fungicides) [4]. Therefore, the knowledge of the physico-chemical properties of this type of compounds is important, particularly those properties that are related with their reactivity.…”

Section: Introductionmentioning

confidence: 99%

Experimental and computational study of the energetics of hydantoin and 2-thiohydantoin

Silva¹,

Cimas²,

Vale³

et al. 2013

The Journal of Chemical Thermodynamics

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The standard (p°= 0.1 MPa) molar energies of combustion of hydantoin and 2-thiohydantoin were measured by static and rotating bomb combustion calorimetry, respectively. The standard molar enthalpies of sublimation, at T = 298.15 K, were derived from the temperature dependence of the vapour pressures of these compounds, measured by the Knudsen-effusion technique, and from high temperature Calvet microcalorimetry. The conjugation of these experimental results enables the calculation of the standard molar enthalpies of formation in the gaseous state, at T = 298.15 K, which are discussed in terms of structural contributions.We have also estimated the gas-phase enthalpy of formation from high-level ab initio molecular orbital calculations at the G3MP2B3 level of theory, being the computed values in good agreement with the experimental ones. Furthermore, this composite approach was also used to obtain information about the gas-phase basicities, proton and electron affinities and adiabatic ionization enthalpies.

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Section: Introductionmentioning

confidence: 99%

Experimental and computational study of the energetics of hydantoin and 2-thiohydantoin

Silva¹,

Cimas²,

Vale³

et al. 2013

The Journal of Chemical Thermodynamics

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“…Hydantoins (imidazolidine-2,4-diones), having a 5-membered ring containing a reactive cyclic urea core, form a wide range of biologically active compounds [1][2][3][4] . Their 2-thioxo analogs, 2-thiohydantoins (2-thioxo-imidazolizin-4-one) also display significant biological activities and are employed as established drugs, fungicides or herbicides [5,6] .…”

Section: Introductionmentioning

confidence: 99%

Crystal Structures and Conformations of 5-Benzyl-2-thiohydantoin and Its 1-Acetylated Derivative

Kunimoto

Ichitani

Ogawa

et al. 2009

Spectroscopy Letters

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Abstract:The crystal structures of 5-benzyl-2-thiohydantoin (5-BTH) and 1-acetyl-5-benzyl-2-thiohydantoin (1-Ac-5-BTH) have been determined by X-ray diffraction. In the 5-BTH crystals, the enantiomeric (R)-and (S)-5-BTH molecules are connected to form cyclic dimers via the hydrogen bonds of the thioamide and the amide moieties. On the other hand, the intermolecular hydrogen bonds in 1-Ac-5-BTH crystals form an infinite chain. These differences 1 SpectroscLett_kunimoto_revised in the hydrogen bond pattern are also discussed in the IR and Raman spectra. The ab initio molecular orbital calculations (Gaussian 03) with 6-31G(d,p) basis set were carried out for 5-BTH and 1-Ac-5-BTH to get the preferred conformation.

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“…1 The chemistry and property of hydantoin and its derivatives have been investigated for more than 140 years. These studies indicate that hydantoin and its derivatives have a broad range of biological activities including anticonvulsants, 2 antiarithmics, 3 antitumor, 4 antidepressants, 5 and antiviral agents. 6 Phenytoin 1 (5,5-diphenylhydantoin, DPH) is one of the best known derivatives of hydantoin.…”

Section: Introductionmentioning

confidence: 93%

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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Hydantoins as antitumor agents

Cited by 62 publications

References 3 publications

Experimental and computational study of the energetics of hydantoin and 2-thiohydantoin

Experimental and computational study of the energetics of hydantoin and 2-thiohydantoin

Crystal Structures and Conformations of 5-Benzyl-2-thiohydantoin and Its 1-Acetylated Derivative

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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