881982-66-7Relevant academic research and scientific papers
Synthesis of 3-O-methylviridicatin analogues with improved anti-TNF-α properties
Ribeiro, Nigel,Tabaka, Helena,Peluso, Jean,Fetzer, Ludivine,Nebigil, Can,Dumont, Serge,Muller, Christian D.,Desaubry, Laurent
, p. 5523 - 5524 (2008/03/13)
We synthesized 3-O-methylviridicatin 1 and several analogues of this fungal metabolite. We showed that replacement of the methoxy moiety by a thiomethyl enhanced dramatically its ability to inhibit TNF-α secretion. These results strongly suggest that 4-phenyl-3-methylthioquinolinone 3 may provide the basis for the development of new anti-inflammatory agents.
Design, synthesis, and evaluation of a new generation of modular nucleophilic glycine equivalents for the efficient synthesis of sterically constrained α-amino acids
Ellis, Trevor K.,Ueki, Hisanori,Yamada, Takeshi,Ohfune, Yasufumi,Soloshonok, Vadim A.
, p. 8572 - 8578 (2007/10/03)
A new generation of modular achiral glycine equivalents have been evaluated with respect to their synthetic utility for the production of tailor-made, sterically constrained α-amino acids, which proved to be the most efficient approach developed to date for the synthesis of symmetrical α,α-disubstituted-α-amino acids. Among the new series of achiral glycine equivalents, one was found to be a superior glycine derivative for the Michael additions with various (R)- or (S)-N-(E-enoyl)-4-phenyl-1,3- oxazolidin-2-ones representing a general and practical synthesis of sterically constrained β-substituted pyroglutamic acids. In particular, the application of these complexes allowed for the preparation of several β-substituted pyroglutamic acids which include electron-releasing and sterically demanding substituents in the structure thus increasing the synthetic efficiency and expanding the generality of these Michael addition reactions.
