58472-47-2Relevant academic research and scientific papers
2-THIO-SUBSTITUTED IMIDAZOLE DERIVATIVES AND THEIR USE IN PHARMACEUTICS
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Page/Page column 33, (2008/06/13)
The invention relates to 2-thio-substituted imidazole derivatives of formula (I), wherein the radicals R1, R2, R3 and m have the meanings as cited in the description. The inventive compounds comprise an immunomodulatory action and/or an action that inhibits the release of cytokines and are thus suited for treating diseases associated with a disorder of the immune system.
The p-(Methylsulfinyl)benzyl Group: A TFA-Stable Carboxyl-Protecting Group Readily Convertible to a TFA-Labile Group
Samanen, James M.,Brandeis, Ester
, p. 561 - 569 (2007/10/02)
The p-(methylsulfinyl)benzyl or Msib ester is recommended as a selectively cleavable carboxyl-protecting group for peptide synthesis.Peptide oramino acid esters of p-(methylsulfinyl)benzyl alcohol, HO-Msib (2), or p-(methylthio)benzyl alcohol, HO-Mtb (1), are readily prepared from the corresponding alcohols or alkyl halides.Msib esters may also be obtained from Mtb esters by oxidation with m-chloroperbenzoic acid.Msib esters are readily deoxygenated by excess Me3SiCl/Ph3P, Me3SiCl/Me2S, or anhydrous hydrogen chloride.Msib esters are exceedingly stable to TFA while Mtb esters solvolyze rapidly.A sample peptide synthesis demonstrates the protection of the C-terminal carboxyl group during synthesis as the Msib ester followed by Msib group removal on completion of synthesis by deoxygenation and TFA solvolysis.The stability of Mtb and Msib esters to typical acid conditions of peptide synthesis is described.The stability of Msib esters to various peptide synthesis conditions suggests that the Msib group should be quite useful as a carboxyl-protecting group in peptide synthesis.
