3467-59-2Relevant articles and documents
Synthesis of Arylamides via Ritter-Type Cleavage of Solid-Supported Aryltriazenes
Wippert, Nicolai A.,Jung, Nicole,Br?se, Stefan
supporting information, p. 568 - 572 (2019/09/03)
A novel route for the synthesis of N-arylamides via the cleavage of aryltriazenes with alkyl or aryl nitriles is presented. We developed a variation of the Ritter reaction that allows the use of acetonitrile as solvent and reagent in reactions with solid-supported precursors. The reaction was optimized for the generation of N-aryl acetamides using a diverse range of immobilized building blocks including o-, m-, and p-substituted aryltriazenes. The cleavage via the Ritter-type conversion was combined with an on-bead cross-coupling reaction of halogen-substituted aryltriazenes with pyrazoles. Additionally, the synthesis of on-bead generated arylboronic ester-substituted triazenes was shown. The developed procedure was further expanded to use other commercially available nitriles, such as acrylonitrile, benzonitrile, and chlorinated alkyl nitriles as suitable reagents for a Ritter-type cleavage of the prepared triazene linkers.
Natural abenquines and synthetic analogues: Preliminary exploration of their cytotoxic activity
Nain-Perez, Amalyn,Barbosa, Luiz C.A.,Rodríguez-Hernández, Diego,Kramell, Annemarie E.,Heller, Lucie,Csuk, René
, p. 1141 - 1144 (2017/06/19)
In this study, we explore the cytotoxic activity of four natural abenquines (2a–d) and fourteen synthetic analogues (2e–j and 3a–h) against a panel of six human cancer cell lines using a SRB assay. It was found that most of the compounds revealed higher levels of cytotoxic activities than naturally occurring abenquines. The analogues carrying ethylpyrrolidinyl and ethylpyrimidinyl with either an acetyl group (2?h–i) or a benzoyl group (3f–g), were the most potent against all human cancer cell lines and displayed EC50 between a range of 0.6–3.4?μM. Notably, of the compounds tested, compound 2i proved the most cytotoxic against both ovarian (A2780) and breast (MCF7) cells, showing EC50?=?0.6 and 0.8?μM respectively. Likewise, the analogues 2i, 3f and 3?g showed strong activity against cell HT29 with EC50?=?0.9?μM for these compounds.
Method for preparing N-aryl amide without solvent and catalyst
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Paragraph 0013; 0014; 0021; 0022, (2017/08/29)
The invention discloses a method for preparing N-aryl amide without a solvent and a catalyst. The method is characterized by obtaining the N-aryl amide under solvent-free and catalyst-free action; a molar ratio of substituted meldrum acid and arylamine is (1 to 5) to (5 to 1). According to the method disclosed by the invention, the defects that acyl chloride, anhydride, a dehydration coupling reagent, the solvent, a phase transfer catalyst or a metal catalyst, and the like are required to be adopted in the prior art are overcome; the method has the following advantages that (1) the substituted meldrum acid is used as an acylating agent, so that pre-activation on carboxylic acid or use of the dehydration coupling reagent is avoided; (2) due to easiness in preparation of the substituted meldrum acid, certain difficult-to-obtain or expensive carboxylic acid and activated derivatives are prevented from being used; (3) a solvent-free mode is adopted, so that the use of a toxic organic solvent or emission of wastewater is avoided; (4) no acid, base or metal catalysts exist, the influence of the acid and the base on sensitive groups and equipment and the residue of metal ions in a product are avoided. A synthesis method disclosed by the invention can play an important role in industrial production for preparing the N-aryl amide and particularly for preparing the N-aryl amide with complex carboxylic acid.
