Synthesis and anti-inflammatory activity of phthalimide derivatives, designed as new thalidomide analogues

Lima, Lı́dia Moreira; Castro, Priscila da Silva; Machado, Alexandre Légora; Fraga, Carlos A.M.; Lugnier, Claire; Moraes, Vera Lúcia Gonçalves de; Barreiro, Eliezer J.

doi:10.1016/s0968-0896(02)00152-9

Cited by 186 publications

(97 citation statements)

References 27 publications

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“…Phthalimides and N-substituted phthalimides are an important class of compounds because of their interesting biological activities [1]. N-butylammonium phthalate is an intermediate in the preparation of N-substituted phthalimides.…”

Section: Discussionmentioning

confidence: 99%

“…

DiscussionPhthalimides and N-substituted phthalimides are an important class of compounds because of their interesting biological activities [1]. N-butylammonium phthalate is an intermediate in the preparation of N-substituted phthalimides.

…”

mentioning

confidence: 99%

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Crystal structure of N-butylammonium phthalate monohydrate, 2(C4H12N)+(C8H4O4)2–·H2O, C16H30N2O5

2012

Zeitschrift für Kristallographie - New Crystal Structures

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Source of materialAll the reagents and solvents from commercial sources were used withoutf urther purification.Amixture of phthalic anhydride (1.52 g, 0.01 mol), butan-1-amine (0.73 g, 0.01 mol) and water (15 ml) was refluxed for 2h.Then the above solution was kept at room temperature for 12 d. Isothermal evaporation gave colourless single crystals of the title compound, suitable for X-ray analysis. DiscussionPhthalimides and N-substituted phthalimides are an important class of compounds because of their interesting biological activities [1]. N-butylammonium phthalate is an intermediate in the preparation of N-substituted phthalimides. In this paper, the crystal structure of the title compound is reported. The asymmetric unit of the title compound contains two Nbutylammonium cations, one phthalate anion and one water solvent molecule. In the anion of the title compound, the dihedral angles formed by the benzene ring and the mean planes of the two carboxylate groups are 41.5(2) and 55.8(2)°, respectively. The atom C4 of one N-butylammonium cation is disordered, while the atomsofC6, C7 and C8 of the another one are disordered. The bond lengths and angles are in agreement with those of the related hexamethylenediammonium phthalate trihydrate [2]. The crystal structure is stabilized by N-H×××Oand O-H×××Ohydrogen bonds.

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Section: Discussionmentioning

confidence: 99%

“…

…”

mentioning

confidence: 99%

Crystal structure of N-butylammonium phthalate monohydrate, 2(C4H12N)+(C8H4O4)2–·H2O, C16H30N2O5

2012

Zeitschrift für Kristallographie - New Crystal Structures

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“…Phthalimides and N-substituted phthalimides are ani mportant class of compounds because of their interesting biologicalactivities [1]. Phthalimides have also served asstarting materials and intermediates for the syntheses of alkaloids [2] and pharmacophores [3].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 5-bromo-2-ethylisoindoline-1,3-dione, C10H8BrNO2

Liang¹,

Li²

2007

Zeitschrift Für Kristallographie - New Crystal Structures

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C 10 H 8 BrNO 2 ,triclinic, P 1 (no. 2), a =5.505(5) Å, b =9.147(8) Å, c =11.79(1) Å, a =105.29(2)°, Source of materialAmixture of 5-bromoisobenzofuran-1,3-dione (0.1 mol), ethaneamine solution (65 %, 0.13 mol) and triethylamine (0.01 mol) was stirredunder reflux in toluene (30 ml) for 5h.After cooling, filtration and drying, the title compound wasobtained. 10 mg of that were dissolved in 15 ml ethanol, and the solutionwaskept atroom temperature for 8d .Naturale vaporation gave colorless single crystals of the title compound, suitable for X-rayanalysis. Discussion

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“…Imides synthesis is of widespread interest as several derivatives of this heterocyclic unit have been found to possess important applications in biology [1][2][3][4][5][6][7], synthetic [8][9][10] and polymer chemistry [11].…”

Section: Introductionmentioning

confidence: 99%

“…Phthalimides are directly obtained from these general methods, but they have also been obtained from a number of unusual starting materials and methods [3][4][5][6][12][13][14][15][16]. The reaction of potassium phthalimide with halogenoalkanes and with a variety of other alkylating agents leads to N-alkylphthalimide.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structural and conformational study of selected N-substituted phthalimides

et al. 2005

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This paper synthesizes N -substituted phthalimides derived from nitrogen heterocycles as potential 5-HT 4 ligands by using the Mitsunobu reaction. Conformational studies of some of the new compounds have been conducted using 1 H and 13 C-NMR spectroscopy. Proton and carbon resonances were achieved through the application of onedimensional selective NOE, two-dimensional NMR techniques -homonuclear COSY-45, NOESY and heteronuclear 1 H-13 C HMQC correlated spectroscopy-and double resonance experiments. The crystal structure of compound 1 was determined by X-ray diffraction.

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Synthesis and anti-inflammatory activity of phthalimide derivatives, designed as new thalidomide analogues

Cited by 186 publications

References 27 publications

Crystal structure of N-butylammonium phthalate monohydrate, 2(C4H12N)+(C8H4O4)2–·H2O, C16H30N2O5

Crystal structure of N-butylammonium phthalate monohydrate, 2(C4H12N)+(C8H4O4)2–·H2O, C16H30N2O5

Crystal structure of 5-bromo-2-ethylisoindoline-1,3-dione, C10H8BrNO2

Synthesis, structural and conformational study of selected N-substituted phthalimides

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