Synthesis and hypolipidemic activity of N-phthalimidomethyl tetra-O-acyl-α-d-mannopyranosides

Srivastava, Rajendra M.; Oliveira, Fernando J. S.; Silva, Ladjane P. da; Filho, João Rufino de Freitas; Oliveira, Shalom P. De; Lima, Vera Lúcia de Menezes

doi:10.1016/s0008-6215(01)00088-x

Cited by 30 publications

(7 citation statements)

References 9 publications

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“…After treatment of 20 mg / kg / day mice with the phthalimideN-[4-chlorophenyl] phthalimide derivative, a 63-47% decrease in cholesterol and triglyceride levels, respectively, was observed. These studies demonstrate that compounds containing the phthalimide group are promising with hypolipidemic agents [7,18,19]. A new phthalimide derivative, LASSBio-1425, showed, among other activities, the ability to reduce serum levels of total cholesterol [248.9 ± 30.6 × 519.…”

Section: Hypolipidemic Activitymentioning

confidence: 98%

Therapeutic Potential of Phthalimide Derivatives: A Review

Júnior

Holanda

RodriguesGambôa

et al. 2019

AJBSR

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Section: Hypolipidemic Activitymentioning

confidence: 98%

Therapeutic Potential of Phthalimide Derivatives: A Review

Júnior

Holanda

RodriguesGambôa

et al. 2019

AJBSR

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“…In 2001, we reported hypolipidemic activity in α-Dmannopyranosides containing phthalimidomethyl function as aglycone. 4 There are other interesting biological aspects of these compounds which have been reviewed in 2003. 5 A recent paper cites the synthesis and anticonvulsant behavior of N-substituted phthalimides.…”

Section: Introductionmentioning

confidence: 99%

“…Uma síntese eficiente e fácil dos compostos: 2-fenillaminometil-isoindol-1,3-diona (5a), 2-[(2-Clorofenilamino)metil]-isoindol-1,3-diona (5b), methyl]-isoindol-1,3-diona (5c), 2-[(4-Clorofenilamino)metil)-isoindol-1,3-diona (5d), 2-[(2-Flúorfenil-amino)metil]-isoindol-1,3-diona (5e), 2-[(3-flúorfenilamino)metil]-isoindol-1,3-diona (5f), metil]-isoindol-1,3-diona (5g), 2-[(2-Nitrofenilamino)metil]-isoindol-1,3-diona (5h), metil]-isoindol-1,3-diona (5i), 2-[(4-Nitrofenilamino)metil]-isoindol-1,3-diona (5j), 2-[1H- (1,2,4)Triazol-3-il-aminometil)-isoindol-1,3-diona (5k) e 2-( [1,2,4]-Triazol-4-il-aminometil)-isoindol-1,3-diona (5l) está descrita. 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.…”

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“…An efficient and easy synthesis of compounds: 2-Phenylaminomethyl-isoindole-1,3-dione (5a), 2-[(2-Clorophenylamino)methyl]-isoindole-1,3-dione (5b), methyl]-isoindole-1,3-dione (5c), 2-[(4-Clorophenylamino)methyl)-isoindole-1,3-dione (5d), 2-[(2-Fluorophenylamino)methyl]-isoindole-1,3-dione (5e), 2-[(3-fluorophenylamino)methyl]-isoindole-1,3-dione (5f), methyl]-isoindole-1,3-dione (5g), 2-[(2-Nitrophenylamino)methyl]-isoindole-1,3-dione (5h), methyl]-isoindole-1,3-dione (5i), methyl]-isoindole-1,3-dione (5j), 2-[1H- (1,2,4)Triazol-3-yl-aminomethyl)-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-hydroxymethyl…”

mentioning

confidence: 99%

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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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“…Thus, this nucleophile-catalyzed annulation reaction provides a novel route to highly electron-deficient dehydropyrans which could be further explored for the synthesis of interesting carbohydrates. [14] A new stereocenter is formed in the ring annulation reaction of acetylene carboxylates with formylchromones, and thus an enantioselective [4+2] annulation could be envisaged. To this end, we initially investigated chiral phosphines as nucleophilic catalysts.…”

mentioning

confidence: 99%