Synthesis and Antidepressant Activity of 5- (4-Dimethylaminobenzyl)imidazolidine-2,4-dione

Wessels, F. L.; Schwan, Thomas J.; Pong, S.F.

doi:10.1002/jps.2600690933

Cited by 50 publications

(13 citation statements)

References 7 publications

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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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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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“…Hydantoins are key functional components of pharmaceuticals, herbicidals, and antifungals . At the same time, hydantoins are valuable intermediates in the chemical and enzymatic syntheses of α‐amino acids, as well as components of optically active polymer and metal complexes …”

Section: Figurementioning

confidence: 99%

A Sustainable, Semi‐Continuous Flow Synthesis of Hydantoins

Vukelić

Koksch

Seeberger

et al. 2016

Chemistry A European J

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Hydantoins are an important class of heterocycles with applications in pharmacy, agriculture, and as intermediates in organic synthesis. Traditional synthetic procedures to access hydantoins are target oriented with multiple synthetic steps and often use reagents that are not commercially available or sustainable. Herein, an efficient process is described for accessing hydantoins starting from commercially available amines using consecutive gas-liquid transformations (oxygen, carbon dioxide). This semi-continuous process produced ten benzylic/aliphatic hydantoins in good overall yields (52-84 %).

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“…Numerous applications have been found for hydantoin derivatives due to their antidepressant [1] and antiviral activities [2], the inhibition of HIV binding to lymphocytes [3], as well as their anticonvulsant and cardiac antiarrhythmic effects [4]. The anticonvulsant properties of phenytoin (Dilantin, Epilan), one of the important drugs employed for the treatment of generalized convulsions, are responsible for the synthesis of many hydantoin analogs [5].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structural Characterization of Spiro(fluorene-9,4′-imidazolidine)-2′,5′-dione and (9H-Fluorene-9-yl)urea

et al. 2012

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Alkaline hydrolysis of spiro(fluorene-9,4 0 -imidazolidine)-2 0 ,5 0 -dione, 2 resulted in ring opening leading to (9H-fluorene-9-yl) urea, 3. The crystal structures 2 and 3 have been determined. Compound 2 crystallizes in the orthorhombic space group P2 1 2 1 2 1 with a = 7.2596(9) Å , b = 9.4497(14) Å , c = 17.304(3) Å and Z = 4 while compound 3 crystallizes in the monoclinic space group P2 1 /c with a = 4.6171(3) Å , b = 14.4713(9) Å , c = 16.9762(14) Å , b = 95.385(7)°and Z = 4. Both molecules have very similar bond lengths and angles pattern, even after the hydantoin ring opening. The 9H-fluorene moiety is nearly planar with rms of 0.007 and 0.032 Å for 2 and 3. The angle between the mean planes of the 9H-fluorene and the hydantoin or carbamide moieties is 86.92(4)°and 71.07(4)°respectively. In both structures N-HÁÁÁO hydrogen bonds connect molecules into the chains along a. The X-ray molecular structure and IR spectra for 2 and 3 are compared with those calculated by the density functional theory method.

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Synthesis and Antidepressant Activity of 5- (4-Dimethylaminobenzyl)imidazolidine-2,4-dione

Cited by 50 publications

References 7 publications

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

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

A Sustainable, Semi‐Continuous Flow Synthesis of Hydantoins

Synthesis and Structural Characterization of Spiro(fluorene-9,4′-imidazolidine)-2′,5′-dione and (9H-Fluorene-9-yl)urea

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