323204-69-9Relevant articles and documents
Amide α,β-Dehydrogenation Using Allyl-Palladium Catalysis and a Hindered Monodentate Anilide
Chen, Yifeng,Turlik, Aneta,Newhouse, Timothy R.
supporting information, p. 1166 - 1169 (2016/02/18)
A practical and direct method for the α,β-dehydrogenation of amides is reported using allyl-palladium catalysis. Critical to the success of this process was the synthesis and application of a novel lithium N-cyclohexyl anilide (LiCyan). The reaction conditions tolerate a wide variety of substrates, including those with acidic heteroatom nucleophiles.
Antifungal, cytotoxic and SAR studies of a series of N-alkyl, N-aryl and N-alkylphenyl-1,4-pyrrolediones and related compounds
Sortino,Garibotto,Cechinel Filho,Gupta,Enriz,Zacchino
experimental part, p. 2823 - 2834 (2011/06/21)
The synthesis, in vitro evaluation and SAR studies of 67 maleimides and derivatives acting as antifungal agents are reported. A detailed SAR study supported by theoretical calculations led us to determine that: an intact maleimido ring appears to be necessary for a strong antifungal activity, dissimilarly affected by the substituents in positions 2 and 3. The best activities were shown by 2,3-nonsubstituted followed by 2,3 dichloro- and 2-methyl-substituted maleimides. They all were fungicide rather than fungistatic enhancing the importance of their antifungal activity. 2,3-Dimethyl and 2,3-diphenyl-maleimides possessed marginal or null activity. The presence of a flexible connecting chain in N-phenylalkyl maleimides appears not to be essential for antifungal activity, although its length shows a correlation with the antifungal behavior, displaying maleimides with alkyl chains of n = 3 and n = 4 the best antifungal activities in most fungi. Different substituents on the benzene ring did not have a clear influence on the activity. Values of chemical potential properties as well as of energy do not sufficiently discriminate between active and inactive compounds. Nevertheless, it was found that, although log P alone is not strong enough to properly predict the antifungal activity, the comparison of its values for compounds within the same sub-type, showed an enhancement of antifungal activity along with an increment of lipophilicity. In addition, the LUMO's electronic clouds of the highly active compounds showed to be concentrated on the imido ring, indicating that their carbon atoms are potential sites for nucleophilic attack. Same results were obtained from MEPs. Most of the active compounds did not show cytotoxic activity against human cancer cell lines and no one possessed hemolytic activity, indicating that their activity is selective to pathogenic fungi and that they are not toxic at MIC concentrations.
N-benzyl-5-hydroxy-3-pyrrolidin-2-one by hydrogen peroxide oxidation of N-benzyl-3-phenylseleno-2-pyrrolidinone
Mun, JiYoung,Smith, Michael B.
, p. 813 - 819 (2007/10/03)
Using the known peroxide oxidation of N-benzyl-3-phenylseleno-2- pyrrolidinone with 30% hydrogen peroxide at -5°C after 3.5 h, we prepared the expected N-benzyl-3-pyrrolin-2-one. However, reaction with 30% hydrogen peroxide for 12 h (-5°C→ambient) gave the unexpected product N-benzyl-5-hydroxy-3-pyrrolidin-2-one in 84% isolated yield. This procedure is a new synthetic route to N-benzyl-5-hydroxy-3-pyrrolidin-2-one. Copyright Taylor & Francis Group, LLC.
