Antihyperlipidemic Activity of Phthalimide Analogues in Rodents

Hall, Iris H.; Voorstad, P. J.; Chapman, James; Cocolas, George H.

doi:10.1002/jps.2600720803

Cited by 30 publications

(6 citation statements)

References 44 publications

(16 reference statements)

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“…Phthalimide derivatives are an interesting class of compounds because they possess important biological activities [1], such as anti-inflammatory [2] and hypolipidemic [3, 4] ones. Glycoconjugates play an important role in many biological processes, including cellular recognition, particularly in cases of inflammation, tumor metastasis, and immune response in bacterial and viral infections [5].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anti-Inflammatory Activity of New Alkyl-Substituted Phthalimide 1H-1,2,3-Triazole Derivatives

Assis

Silva

Oliveira

et al. 2012

The Scientific World Journal

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Four new 1,2,3-triazole phthalimide derivatives with a potent anti-inflammatory activity have been synthesized in the good yields by the 1,3-dipolar cycloaddition reaction from N-(azido-alkyl)phthalimides and terminal alkynes. The anti-inflammatory activity was determined by injecting carrageenan through the plantar tissue of the right hind paw of Swiss white mice to produce inflammation. All the compounds 3a–c and 5a–c exhibited an important anti-inflammatory activity; the best activity was found for the compounds 3b and 5c, which showed to be able to decrease by 69% and 56.2% carrageenan-induced edema in mice. These compounds may also offer a future promise as a new anti-inflammatory agent.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Anti-Inflammatory Activity of New Alkyl-Substituted Phthalimide 1H-1,2,3-Triazole Derivatives

Assis

Silva

Oliveira

et al. 2012

The Scientific World Journal

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“…Later on, Hall and co-workers 2,3 reported the antihyperlipidemic activity of phthalimide analogs in rodents and also the same activity was found by the administration of ortho-(Nphthalimido)acetophenone in sprague dawley rats. In 2001, we reported hypolipidemic activity in α-Dmannopyranosides containing phthalimidomethyl function as aglycone.…”

Section: Introductionmentioning

confidence: 74%

Conventional and microwave-assisted reaction of N-hydroxymethylphthalimide with arylamines: synthesis of N-(arylaminomethyl)-phthalimides

Sena

Srivastava

Simone

et al. 2007

J. Braz. Chem. Soc.

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Uma síntese eficiente e fácil dos compostos: 2-fenillaminometil-isoindol-1,3-diona (5a), 2-[(2-Clorofenilamino)metil]-isoindol-1,3-diona (5b), 2-[(3-Clorofenilamino)methyl]-isoindol-1,3-diona (5c), 2-[(4-Clorofenilamino)metil)-isoindol-1,A síntese foi realizada partindo-se da N-hidróximetilftalimida 3 e de aril-e [1,2,4-triazol-3-e 4-il]-aminas 4a-l através de procedimentos convencional e mediado por microondas. A reação de 3 com 4l aconteceu rapidamente e com altos rendimentos. Está descrita uma comparação entre estes dois métodos. São propostos três prováveis mecanismos de formação das N-(arilaminometil)-ftalimidas (um em solução e os outros dois em condições de aceleração por microondas). As análises cristalográficas de 5d forneceram as informações apropiadas sobre a conformação da mesma. Cálculos de orbitais moleculares Ab initio de 5d empregando um conjunto de base 6-31G* foi realizado e os resultados concordaram com os dados de raio-X.An efficient and easy synthesis of compounds: 2-Phenylaminomethyl-isoindole-1,3-dione (5k) and 2-([1,2,4]-Triazole-4-yl-aminomethyl)-isoindole-1,3-dione (5l), is described. The general synthesis procedure starts from N-hydroxymethylphthalimide 3 and aryl-and [1,2,4-triazol-3-and 4-yl]-amines 4a-l by conventional and solventfree microwave-mediated. The reaction of 3 with 4l turned out to be a very rapid and highyielding one. A comparison of these two methods has been made. Three probable mechanisms of formation of N-(arylaminomethyl)-phthalimides (one in the solution phase and two in the microwave-accelerated conditions are proposed. Crystallographic analyses of 5d furnished the correct conformation of this molecule. Ab initio molecular orbital calculations of 5d using 6-31G* basis set were performed and the results were comparable to the X-ray data.

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“…(Chapman et al, 1979). Later on, Hall and co-workers reported the antihyperlipidemic activity of phthalimide analogs in rodents and also the same activity was found by the administration of ortho-(N-phthalimido) acetophenone in sprague dawley rats (Hall et al, 1983;1987). In 2001, Srivastava et al reported hypolipidemic activity in α-D-mannopyranosides containing phthalimidomethyl function as aglycone (Srivastava et al, 2001).…”

Section: Crystal Datamentioning

confidence: 92%

“…For general background, see: Chapman et al (1979); Hall et al (1983Hall et al ( , 1987; Srivastava et al (2001); Cechinel et al (2003); Abdel-Hafez (2004); Antunes et al (2003); Sena et al (2007). For ring motif details, see: Bernstein et al (1995); Etter (1990).…”

Section: Related Literaturementioning

confidence: 99%

5,6-Dichloro-2-(2-hydroxyphenyl)isoindoline-1,3-dione

Büyükgüngör

Odabaşoğlu

2008

Acta Cryst E

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In the molecule of the title compound, C14H7Cl2NO3, the phthalimide ring system is virtually planar, with a dihedral angle between the fused five- and six-membered rings of 4.02 (3)°. In the crystal structure, intermolecular C—H⋯O and O—H⋯O hydrogen bonds and C—Cl⋯O close contacts [Cl⋯O = 3.0123 (13) Å and C—Cl⋯O = 171.14 (7)°] link the molecules, generating R 2 2(16), R 4 2(19) and R 4 4(22) ring motifs by C(6) chains to form a three-dimensional network. A weak π–π interaction between the six-membered rings of the phthalimide ring systems further stabilizes the structure, with a centroid–centroid distance of 3.666 (3) Å and an interplanar separation of 3.568 Å.

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Antihyperlipidemic Activity of Phthalimide Analogues in Rodents

Cited by 30 publications

References 44 publications

Synthesis and Anti-Inflammatory Activity of New Alkyl-Substituted Phthalimide 1H-1,2,3-Triazole Derivatives

Synthesis and Anti-Inflammatory Activity of New Alkyl-Substituted Phthalimide 1H-1,2,3-Triazole Derivatives

Conventional and microwave-assisted reaction of N-hydroxymethylphthalimide with arylamines: synthesis of N-(arylaminomethyl)-phthalimides

5,6-Dichloro-2-(2-hydroxyphenyl)isoindoline-1,3-dione

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