- A catalyst-free, waste-less ethanol-based solvothermal synthesis of amides
-
A green, one-pot approach based on the solvothermal amidation of carboxylic acids with amines has been developed for the synthesis of diverse aliphatic and aromatic amides. It does not require the use of catalysts or coupling reagents and it occurs in the presence of ethanol that has been proved to have a key role in the process. The proposed strategy is also extendable to biologically active amides and could represent a low-cost and waste-less alternative to the common synthetic pathways.
- Dalu, Francesca,Scorciapino, Mariano A.,Cara, Claudio,Luridiana, Alberto,Musinu, Anna,Casu, Mariano,Secci, Francesco,Cannas, Carla
-
supporting information
p. 375 - 381
(2018/02/07)
-
- Antiproliferative activity of synthetic fatty acid amides from renewable resources
-
In the work, the in vitro antiproliferative activity of a series of synthetic fatty acid amides were investigated in seven cancer cell lines. The study revealed that most of the compounds showed antiproliferative activity against tested tumor cell lines, mainly on human glioma cells (U251) and human ovarian cancer cells with a multiple drug-resistant phenotype (NCI-ADR/RES). In addition, the fatty methyl benzylamide derived from ricinoleic acid (with the fatty acid obtained from castor oil, a renewable resource) showed a high selectivity with potent growth inhibition and cell death for the glioma cell line - the most aggressive CNS cancer.
- Dos Santos, Daiane S.,Piovesan, Luciana A.,D'Oca, Caroline R. Montes,Hack, Carolina R. Lopes,Treptow, Tamara G.M.,Rodrigues, Marieli O.,Vendramini-Costa, Débora B.,Ruiz, Ana Lucia T.G.,De Carvalho, Jo?o Ernesto,D'Oca, Marcelo G. Montes
-
p. 340 - 347
(2015/02/02)
-
- Synthesis and antituberculosis activity of new fatty acid amides
-
This work reports the synthesis of new fatty acid amides from C16:0, 18:0, 18:1, 18:1 (OH), and 18:2 fatty acids families with cyclic and acyclic amines and demonstrate for the first time the activity of these compounds as antituberculosis agents against Mycobacterium tuberculosis H37Rv, M. tuberculosis rifampicin resistance (ATCC 35338), and M. tuberculosis isoniazid resistance (ATCC 35822). The fatty acid amides derivate from ricinoleic acid were the most potent one among a series of tested compounds, with a MIC 6.25 μg/mL for resistance strains.
- D'Oca, Caroline Da Ros Montes,Coelho, Tatiane,Marinho, Tamara Germani,Hack, Carolina Rosa Lopes,Da Costa Duarte, Rodrigo,Da Silva, Pedro Almeida,D'Oca, Marcelo Gonalves Montes
-
scheme or table
p. 5255 - 5257
(2010/10/03)
-
- Eicosapentaenoic acid enrichment from sardine oil by argentation chromatography
-
Eicosapentaenoic acid (EPA) derived from chemically hydrolyzed sardine oil was concentrated by urea fractionation using methanol at different temperatures (2, 4, and 6°C) and urea/fatty acid ratios (2:1, 3:1, and 4:1 w/w) and purified by argentation neutral alumina column chromatography. The individual fatty acids were determined as fatty acid methyl esters (FAME) by gas-liquid chromatography and gas chromatography-mass spectroscopy as FAME and N-acyl pyrrolidides. In the mass fragmentation pattern of FAME, the base peak was assigned to be the 1-methoxyethenol moiety (m/z = 74) obtained by McLafferty rearrangement. Formation of the cyclic tropylium ion (m/z = 91) in fatty acids with four or more double bonds was apparent in FAME-PUFAs. The base peak of N-acyl pyrrolidides was the McLafferty rearrangement ion, 1-(pyrrolidin-1-yl) ethenol (m/z = 113). The highest concentration of EPA (47.78%) was obtained at the crystallization temperature of 4°C with a urea/fatty acid ratio of 4:1 (w/w) with 93.74% yield. After complexation of saturated and less unsaturated fatty acids by urea complexation, argentation chromatography resulted in an EPA of high purity (99.6%) with an overall recovery of 54.09% using 50% diethyl ether/n-hexane as eluting solvent. The peroxide (POV) and thiobarbituric acid (TBS) values were found to be highest (4.0 mequiv of O2/kg and 5.2 mg of malondialdehyde/kg, respectively) during urea fractionation at the higher crystallization temperature (6°C) and higher urea/fatty acid ratio (4:1).
- Chakraborty, Kajal,Raj, R. Paul
-
p. 7586 - 7595
(2008/09/19)
-
- One pot direct synthesis of amides or oxazolines from carboxylic acids using Deoxo-Fluor reagent
-
A mild and highly efficient one pot-one step condensation and/or condensation-cyclization of various acids to amides and/or oxazolines using Deoxo-Fluor reagents is described. Parallel syntheses of various free fatty acids with 2-amino-2,2-dimethyl-1-propanol resulted with excellent yields.
- Kangani, Cyrous O.,Kelley, David E.
-
p. 8917 - 8920
(2007/10/03)
-
- Direct Aminolysis of Nonactivated and Thermally Unstable Esters at High Pressure
-
The preparation of the amides 3 from a wide variety of nonactivated esters 1 and secondary amines 2 has been achieved at 8 kbar and around 45 deg C; scope and limitations are discussed.The method was also successfully applied for the aminolysis of alkyl 2-arylsulfinylacetates 7 that are relatively sensitive to heat. - Key Words: Aminolysis/ High-pressure synthesis
- Matsumoto, Kiyoshi,Hashimoto, Shiro,Uchida, Takane,Okamoto, Tadashi,Otani, Shinichi
-
p. 1357 - 1364
(2007/10/02)
-
- Triazolopyridine, a New Derivative for the Structural Determination of Fatty Acids by Gas Chromatography/Mass Spectrometry
-
Triazolopyridine is proposed as a new derivative for the location of branches and double bonds in fatty acids.It is compared with previously used derivatives and found to be clearly superior to the pyrrolidide and slightly superior to the β-picolinyl ester with regard to the structure-specific fragmentation pattern.It is prepared by reacting the activated acid with 2-hydrazinopyridine followed by cyclization.
- Vetter, Walter,Meister, Walter,Oesterhelt, Gottfried
-
p. 566 - 572
(2007/10/02)
-