628-77-3Relevant articles and documents
Exploring the effect of chirality on the therapeutic potential of N-alkyl-deoxyiminosugars: anti-inflammatory response to Pseudomonas aeruginosa infections for application in CF lung disease
De Fenza, Maria,D'Alonzo, Daniele,Esposito, Anna,Munari, Silvia,Loberto, Nicoletta,Santangelo, Alessandra,Lampronti, Ilaria,Tamanini, Anna,Rossi, Alice,Ranucci, Serena,De Fino, Ida,Bragonzi, Alessandra,Aureli, Massimo,Bassi, Rosaria,Tironi, Matteo,Lippi, Giuseppe,Gambari, Roberto,Cabrini, Giulio,Palumbo, Giovanni,Dechecchi, Maria Cristina,Guaragna, Annalisa
supporting information, p. 63 - 71 (2019/05/10)
In the frame of a research program aimed to explore the relationship between chirality of iminosugars and their therapeutic potential, herein we report the synthesis of N-akyl L-deoxyiminosugars and the evaluation of the anti-inflammatory properties of selected candidates for the treatment of Pseudomonas aeruginosa infections in Cystic Fibrosis (CF)lung disease. Target glycomimetics were prepared by the shortest and most convenient approach reported to date, relying on the use of the well-known PS-TPP/I2 reagent system to prepare reactive alkoxyalkyl iodides, acting as key intermediates. Iminosugars ent-1-3 demonstrated to efficiently reduce the inflammatory response induced by P. aeruginosa in CuFi cells, either alone or in synergistic combination with their D-enantiomers, by selectively inhibiting NLGase. Surprisingly, the evaluation in murine models of lung disease showed that the amount of ent-1 required to reduce the recruitment of neutrophils was 40-fold lower than that of the corresponding D-enantiomer. The remarkably low dosage of the L-iminosugar, combined with its inability to act as inhibitor for most glycosidases, is expected to limit the onset of undesired effects, which are typically associated with the administration of its D-counterpart. Biological results herein obtained place ent-1 and congeners among the earliest examples of L-iminosugars acting as anti-inflammatory agents for therapeutic applications in Cystic Fibrosis.
Pheromone synthesis. Part 243: Synthesis and biological evaluation of (3R,13R,1′S)-1′-ethyl-2′-methylpropyl 3,13-dimethylpentadecanoate, the major component of the sex pheromone of Paulownia bagworm, Clania variegata, and its stereoisomers
Mori, Kenji,Tashiro, Takuya,Zhao, Boguang,Suckling, David M.,El-Sayed, Ashraf M.
experimental part, p. 2642 - 2653 (2010/05/18)
All of the four stereoisomers of (1′S)-1′-ethyl-2′-methylpropyl 3,13-dimethylpentadecanoate, the major component of the female sex pheromone of Clania variegata, were synthesized by employing olefin cross metathesis as the key reaction and starting from (R)- or (S)-2-methyl-1-butanol, (R)- or (S)-citronellal, and (S)-2-methyl-3-pentanol. Their bioassay revealed the (3R,13R,1′S)-isomer as the bioactive one, whose more efficient synthesis was achieved in two different ways by employing Wittig reaction as the key step.
Ring-Opening Iodo- and Bromosilation of Cyclic Ethers by Treatment with Iodo- and Bromotrialkylsilane Equivalents
Ohshita, Joji,Iwata, Arihiro,Kanetani, Fujio,Kunai, Atsutaka,Yamamoto, Yasushi,Matui, Chinami
, p. 8024 - 8026 (2007/10/03)
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