Microwave assisted synthesis of N-Arylphthalamic acids with hyperlipidemic activity

Sena, Vera L. M.; Srivastava, Rajendra M.; Oliveira, Shalom P. De; Lima, Vera Lúcia de Menezes

doi:10.1016/s0960-894x(01)00540-6

Cited by 9 publications

(3 citation statements)

References 23 publications

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“…The azide-phthalimides (2a-d) were synthesized, according to the literature description, in 60-93% yields. 24) Recently, our research group developed an efficient click protocol for the preparation of N-phthalimidoalkyl 1H-1,2,3triazoles using N,N-dimethylformamide (DMF) as the solvent, copper iodide (CuI) and triethylamine (Et 3 N) under ultrasound irradiation for 30 min at room temperature. 24) Under these conditions, eight compounds 3a-d and 4a-d were synthesized in good to excellent yields of 70-96% (Chart 1 and Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…Phthalimide and 1,2,3-triazole nucleus have been applied as a strategy to design new molecular hybrids. In previous studies, we reported on the synthesis 23,24) and biological activities 19,21,25,26) of these structures to valorize them as promising "drug-like" molecules. One example of phthalimide-triazole molecule was synthesized and studied for its antiinflammatory activities.…”

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confidence: 99%

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Design and Synthesis of Triazole-Phthalimide Hybrids with Anti-inflammatory Activity

Assis

Silva

et al. 2019

CHEMICAL & PHARMACEUTICAL BULLETIN

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Phthalimido-alkyl-1H-1,2,3-triazole derivatives 3a-d and 4a-d were efficiently synthesized using 1,3-dipolar cycloaddition reaction. Anti-inflammatory activity and toxicity studies were performed. The results demonstrated that all the tested compounds reduced carrageenan-induced paw edema and indicated no lethality for toxicity against Artemia salina and acute toxicity in vivo (LD 50 up to 1 g kg 1). Furthermore, the structure of phthalimide linked to phenyl group proved to be more active than the compounds containing benzothiazole moiety. Structural modifications such as removal of the phthalimide group and subsequent acetylation, to exemplify a non-cyclic amide, demonstrate that the phthalimide and triazole moieties are important for design of potent candidates with anti-inflammatory drug proprieties. Docking into the cyclooxygenase-2 (COX-2) confirms the importance of the phthalimide and triazole groups in the anti-inflammatory activity. The histopathological studies showed that the compounds 3a-d and 4a-d did not cause serious pathological lesions liver or kidneys.

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Section: Resultsmentioning

confidence: 99%

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confidence: 99%

Design and Synthesis of Triazole-Phthalimide Hybrids with Anti-inflammatory Activity

Assis

Silva

et al. 2019

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Recently, the synthesis of N -aryl-2-carbamoylbenzoic acids under microwave assisted conditions from phthalic anhydride and aryl or heterocyclic amines in the absence of solvent with yields 51–99% has been reported [5]. Significant research findings show that these N -arylphthalamic acids induce hyperlipidemia in Swiss white mice and also an increase in body weight of the animals, in contrast with the hypolipidemic activity showed by their phthalimide analogues [6].…”

Section: Introductionmentioning

confidence: 99%

A Novel and Highly Regioselective Synthesis of New Carbamoylcarboxylic Acids from Dianhydrides

Ochoa-Terán

Estrada-Manjarrez

Martinez‐Quiroz

et al. 2014

The Scientific World Journal

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A regioselective synthesis has been developed for the preparation of a series of N,N′-disubstituted 4,4′-carbonylbis(carbamoylbenzoic) acids and N,N′-disubstituted bis(carbamoyl) terephthalic acids by treatment of 3,3′,4,4′-benzophenonetetracarboxylic dianhydride (1) and 1,2,4,5-benzenetetracarboxylic dianhydride (2) with arylalkyl primary amines (A-N). The carbamoylcarboxylic acid derivatives were synthesized with good yield and high purity. The specific reaction conditions were established to obtain carbamoyl and carboxylic acid functionalities over the thermodynamically most favored imide group. Products derived from both anhydrides 1 and 2 were isolated as pure regioisomeric compounds under innovative experimental conditions. The chemo- and regioselectivity of products derived from dianhydrides were determined by NMR spectroscopy and confirmed by density functional theory (DFT). All products were characterized by NMR, FTIR, and MS.

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ChemInform Abstract: Microwave Assisted Synthesis of N‐Arylphthalamic Acids with Hyperlipidemic Activity.

et al. 2002

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carboxylic amidescarboxylic amides (benzene compounds) Q 0490 -117Microwave Assisted Synthesis of N-Arylphthalamic Acids with Hyperlipidemic Activity.-A series of N-arylphthalamic acids (III) (9 examples) are synthesized by microwave-assisted reaction of phthalic anhydride with aryl amines. These acids induce hyperlipidemia and also increase animals' body weight.-(SENA, VERA L. M.; SRIVASTAVA, RAJENDRA M.; OLIVEIRA, SHALOM P.; LIMA, VERA L. M.; Bioorg. Med. Chem. Lett. 11 (2001Lett. 11 ( ) 20, 2671Lett. 11 ( -2674 Dep. Quim. Fundam., Univ. Fed. Pernambuco, 50670 Recife, Brazil; EN)

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Microwave assisted synthesis of N-Arylphthalamic acids with hyperlipidemic activity

Cited by 9 publications

References 23 publications

Design and Synthesis of Triazole-Phthalimide Hybrids with Anti-inflammatory Activity

Design and Synthesis of Triazole-Phthalimide Hybrids with Anti-inflammatory Activity

A Novel and Highly Regioselective Synthesis of New Carbamoylcarboxylic Acids from Dianhydrides

ChemInform Abstract: Microwave Assisted Synthesis of N‐Arylphthalamic Acids with Hyperlipidemic Activity.

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