In 2014,Angewandte Chemie, International Edition included an article by Jacob, Nicholas T.; Lockner, Jonathan W.; Kravchenko, Vladimir V.; Janda, Kim D.. Safety of Methyl 2-(methylthio)-4,5-dihydro-1H-imidazole-1-carboxylate. The article was titled 《Pharmacophore Reassignment for Induction of the Immunosurveillance Cytokine TRAIL》. The information in the text is summarized as follows:
Tumor necrosis factor (TNF)-related apoptosis-inducing ligand (TRAIL) is an immunosurveillance cytokine that kills cancer cells but demonstrates little toxicity against normal cells. While investigating the TRAIL-inducing imidazolinopyrimidinone TIC10, a misassignment of its active structure was uncovered. Syntheses of the two isomers, corresponding to the published and reassigned structures, are reported. The ability of each to induce TRAIL expression in macrophages was investigated and only the compound corresponding to the reassigned structure shows the originally reported activity; the compound corresponding to the published structure is inactive. Importantly, this structural reassignment has furnished a previously unknown antitumor pharmacophore. The results came from multiple reactions, including the reaction of Methyl 2-(methylthio)-4,5-dihydro-1H-imidazole-1-carboxylate(cas: 60546-77-2Safety of Methyl 2-(methylthio)-4,5-dihydro-1H-imidazole-1-carboxylate)
Methyl 2-(methylthio)-4,5-dihydro-1H-imidazole-1-carboxylate(cas: 60546-77-2) belongs to imidazoles.Although other azole heterocycles are ubiquitous in a wide range of biologically active natural products, imidazole rings occur predominantly in the natural amino acid histidine. In addition, imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies. Safety of Methyl 2-(methylthio)-4,5-dihydro-1H-imidazole-1-carboxylate
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem