Do isolamento à síntese da convolutamidina A

Silva, Rosângela B.; Torres, Javier Rodríguez; Garden, Simon J.; Violante, F. de Almeida; Rezende, Michelle J. C.; Silva, Bárbara V. da; Pinto, Ângelo C.

doi:10.1590/s0100-40422008000400035

Cited by 4 publications

(3 citation statements)

References 10 publications

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“…In the reactions with diethylamine, 32,33 there was total consumption of the starting material over periods that varied from 7 to 21 days at room temperature. The different yields can be justified by the different solubility of the products in the liquid-liquid extraction solvent (ethyl acetate).…”

Section: Chemistrymentioning

confidence: 99%

A Facile Synthesis of Novel Isatinspirooxazine Derivatives and Potential in vitro Anti-Proliferative Activity

Santos

Guerra

Bernardino

et al. 2018

J. Braz. Chem. Soc.

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Novel isatinspirooxazine derivatives were designed and synthesized as potential anti-proliferative agents. The new compounds were obtained from aldol condensation reactions between isatin and 3-(hydroxyimino)butan-2-one in the presence of an organic base in order to generate an aldol adduct, followed by cyclization in trifluoroacetic acid, providing the desired isatinspirooxazines in 30 to 80% yield. All the synthesized compounds, including the starting material and the synthetic intermediates, were tested for in vitro anti-proliferative activity against cell lines MCF-7 and MDA-MB231 (breast cancer) and A549 (lung cancer), highlighting the compound 4-methyl,5'-methyl-spiro[(5-aza-4-eno-3-one-cyclohexane)-1,3'-(1H-indol-one)] with an IC 50 (half maximal inhibitory concentration) = 0.34 μM, more potent than the reference drug, doxorubicin (IC 50 = 1.88 μM), in breast cancer line MDA-MB231.

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Section: Chemistrymentioning

confidence: 99%

A Facile Synthesis of Novel Isatinspirooxazine Derivatives and Potential in vitro Anti-Proliferative Activity

Santos

Guerra

Bernardino

et al. 2018

J. Braz. Chem. Soc.

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“…Os catalisadores heterogêneos podem minimizar os impactos ambientais gerados pela eliminação de rejeitos químicos quando se utiliza o ácido sulfúrico como catalisador, atendendo aos princípios da Química Verde. [20][21][22][23][24][25]…”

Section: Dean-starkunclassified

Synthesis of Fruity Flavor Esters: An Experiment for Undergraduate Courses within one of the Principles of Green Chemistry

Oliveira¹,

Souza²,

Santos³

et al. 2014

Revista Virtual De Química

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The esters are among the classes of organic substances responsible for the pleasant odor of flowers and fruits. The synthesis of these substances occurs through the reaction between carboxylic acids and alcohols, usually catalyzed by BrÖnsted-Lowry acid. This work presents the results of different methods of esterification using homogeneous catalysis like sulfuric acid and heterogeneous catalysis with commercial sulfonic resin (Amberlyst 35) and montmorilonite clay. All reactions were carried out with heating under reflux and repeated with use of the system Dean-Stark to remove water produced in the reaction. The use of Dean-Stark moves the equilibrium to the formation of the products and, consequently, reduces significantly the reaction time. The heterogeneous catalysts proved to be advantageous relatively to the use of sulfuric acid since the process of isolation is easier and provides an approach of Green Chemistry in Undergraduate experimental classes.

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“…Furthermore isatin and its derivatives are important raw materials for drug synthesis. [4][5][6] Thus 5-fluoroisatin is the precursor of the Sunitinib (Sutent®) drug, approved by the Food and Drugs Administration (FDA) in 2006 for treatment of renal cell carcinoma (RCC) and gastrointestinal stromal tumor (GIST). 7 In addition to antitumor activity these substances exhibit antiviral, anti-inflammatory and anticonvulsant properties.…”

Section: Introductionmentioning

confidence: 99%

Counter-Current chromatography separation of isatin derivatives using the sandmeyer methodology

Almeida

Leitão

Silva

et al. 2010

J. Braz. Chem. Soc.

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Do isolamento à síntese da convolutamidina A

Cited by 4 publications

References 10 publications

A Facile Synthesis of Novel Isatinspirooxazine Derivatives and Potential in vitro Anti-Proliferative Activity

A Facile Synthesis of Novel Isatinspirooxazine Derivatives and Potential in vitro Anti-Proliferative Activity

Synthesis of Fruity Flavor Esters: An Experiment for Undergraduate Courses within one of the Principles of Green Chemistry

Counter-Current chromatography separation of isatin derivatives using the sandmeyer methodology

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