- A novel piperine analogue exerts in vivo antitumor effect by inducing oxidative, antiangiogenic and immunomodulatory actions
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Structural diversity characterizes natural products as prototypes for design of lead compounds. The aim of this study was to synthetize, and to evaluate the toxicity and antitumor action of a new piperine analogue, the butyl 4-(4-nitrobenzoate)-piperinoat
- Abrantes, Renata Albuquerque de,Athayde-Filho, Petr?nio Filgueiras de,Batista, Tatianne Mota,Brand?o, Maria Cláudia Rodrigues,Cavalcanti, Raquel Fragoso Pereira,Duarte, Samia Sousa,Farias, Davi Felipe,Ferreira, Rafael Carlos,Leite, Fagner Carvalho,Lisboa, Thaís Mangeon Honorato,Mangueira, Vivianne Mendes,Medeiros, Karina Carla de Paula,Silva, Daiana Karla Frade,Sobral, Marianna Vieira,Sousa, Tatyanna Kélvia Gomes de,Trindade, Emmely Oliveira da
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- Synthesis, in silico study and antimicrobial activity of new piperine derivatives containing substituted δ-esters
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A series of fifteen new piperine-derived diesters was synthesized through the substitution reaction between the salt of piperic acid, obtained through piperine basic hydrolysis, with the δ-chloro-esters, obtained through the cleavage of tetrahydrofuran (THF) with acyl chlorides in the presence of ZnCl2. The final compounds were obtained with yields ranging from 50 to 84% and were characterized by infrared (IR) and 1H and 13C nuclear magnetic resonance spectroscopy (NMR). The new compounds were evaluated in silico in regard to their ADME (absorption, distribution, metabolism, and excretion) properties, and in vitro for their antimicrobial activity against bacteria strains (Staphylococcus aureus and Pseudomonas aeruginosas), yeast fungi (Candida albicans and C. tropicalis) and filamentous fungi (Aspergillus fumigatus, A. flavus and A. niger). The results from the in silico studies of Lipinski's rule of five showed that most compounds present good pharmacological possibilities, and the results from in vitro antimicrobial activity showed that 8 of the 15 synthesized compounds displayed antimicrobial activity, inhibiting the growth of 40-80% of tested strains, with a minimum inhibitory concentration (MIC) interval ranging from 1024 to 256 μg mL-1
- Barbosa-Filho, José M.,Brandao, Maria C. R.,De Athayde-Filho, Petr?nio F.,Dutra, Thalisson F.,Lima, Edeltrudes O.,Lira, Bruno F.,Neto, Hermes Diniz,Trindade, Emmely O.
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p. 2590 - 2602
(2020/11/18)
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- QUINONE BASED NITRIC OXIDE DONATING COMPOUNDS FOR OPHTHALMIC USE
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The present invention relates to nitric oxide donor compounds having a quinone based structure of formula (I), wherein R1 to R6, n, m and p are as defined in claim 1, compositions thereof and said compounds for use in the treatment and/or prophylaxis of glaucoma and ocular hypertension.
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Page/Page column 38-39
(2014/11/11)
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- QUINONE BASED NITRIC OXIDE DONATING COMPOUNDS
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The present invention relates to nitric oxide donor compounds having a quinone based structure of formula (I), wherein R1 to R6, m, n and p are as defined in claim 1, to processes for their preparation and to their use in the treatment of pathological conditions where a deficit of NO plays an important role in their pathogenesis, such as pulmonary arterial hypertension, Sickle cell disease, systemic sclerosis and scleroderma, muscular dystrophies, Duchenne's muscular dystrophy and Becker's muscular dystrophy, vascular dysfunctions.
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Page/Page column 35-36
(2014/11/11)
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- QUINONE BASED NITRIC OXIDE DONATING COMPOUNDS
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The present invention relates to nitric oxide donor compounds having a quinone based structure, to processes for their preparation and to their use in the treatment of pathological conditions where a deficit of NO plays an important role in their pathogen
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Page/Page column 24
(2014/11/11)
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- Synthesis of δ- And ε-cyanoesters by zinc-catalyzed ring-opening of cyclic ethers with acid chlorides and subsequent cyanation
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In the present study, the zinc-catalyzed cleavage of cyclic ethers with acid halides as nucleophiles to yield chloroesters with different chain length has been investigated in detail. In the presence of straightforward and commercially available zinc salts as pre-catalysts excellent yields and selectivities were feasible. After studying the reaction conditions and the scope of the method, several efforts were carried out to understand the reaction mechanism. The obtained chloroesters were subsequently converted to δ- and ε-cyano esters, which are useful precursors in natural product synthesis. Graphical Abstract: [Figure not available: see fulltext.]
- Enthaler, Stephan,Weidauer, Maik
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experimental part
p. 168 - 175
(2012/03/27)
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- Use of magnesium (turnings) as a powerful catalyst for the o-acylative cleavage of tetrahydrofuran
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In a short reaction time, acyl chlorides and dry tetrahydrofuran react in the presence of a catalytic amount of magnesium turnings (Mg) at 25 °C to give 4-chlorobutyl esters in excellent yields. Copyright
- Pasha,Manjula, Krishnappa
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experimental part
p. 2309 - 2314
(2011/06/27)
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- Single-pot conversion of an acid to the corresponding 4-chlorobutyl ester
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A single pot conversion of carboxylic acids into the corresponding 4-chlorobutyl esters has been achieved by a novel procedure. The intermediate acid chlorides are not isolated. The double bond and aromatic methoxy group survive the mild reaction conditions. In almost all the examples studied the products are purified by simple flash chromatography.
- Pal, Sutanuka,Pal, Sudhir Chandra
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experimental part
p. 596 - 599
(2012/04/18)
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- Simple and efficient method for the synthesis of δ-chloroesters from tetrahydrofuran and acyl chlorides in the presence of catalytic iodine
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Acyl chlorides and dry tetrahydrofuran (THF) in the presence of catalytic amounts of iodine at 25°C give δ-chloroesters in excellent yields. Copyright Taylor & Francis Group, LLC.
- Pasha,Manjula
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p. 927 - 932
(2007/10/03)
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- Synthetic biological response modifiers. Part II. Synthesis and immunomodulatory properties of some: N2-[ω-pyrimidin-1-yl)carboxyalkyl]-L-arginines
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The synthesis and chemical and physical properties of some N2-[ω-(pyrimidin-1-yl)carboxyalchyl]-L-arginines are here described. Experiments of immunopharmacological evaluations are also described.
- Stradi,Pini,Rossi,Cornaglia Ferraris
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p. 799 - 804
(2007/10/02)
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