114766-05-1Relevant articles and documents
Efficient synthesis of a 5-HT2C receptor agonist precursor
Peters, Rene,Waldmeier, Pius,Joncour, Agnes
, p. 508 - 512 (2005)
A short, scaleable, synthetic approach toward the tricyclic indole derivative 2, an intermediate in the synthesis of the 5-HT2C agonist 1, is described. The synthesis started with Williamson etherification of inexpensive 4-nitro-3-methylphenol
Synthesis and biological evaluation of indolyl-pyridinyl-propenones having either methuosis or microtubule disruption activity
Trabbic, Christopher J.,Overmeyer, Jean H.,Alexander, Evan M.,Crissman, Emily J.,Kvale, Heather M.,Smith, Marcie A.,Erhardt, Paul W.,Maltese, William A.
, p. 2489 - 2512 (2015/03/30)
Methuosis is a form of nonapoptotic cell death characterized by an accumulation of macropinosome-derived vacuoles with eventual loss of membrane integrity. Small molecules inducing methuosis could offer significant advantages compared to more traditional anticancer drug therapies that typically rely on apoptosis. Herein we further define the effects of chemical substitutions at the 2-and 5-indolyl positions on our lead compound 3-(5-methoxy-2-methyl-1H-indol-3-yl)-1-(4-pyridinyl)-2-propene-1-one (MOMIPP). We have identified a number of compounds that induce methuosis at similar potencies, including an interesting analogue having a hydroxypropyl substituent at the 2-position. In addition, we have discovered that certain substitutions on the 2-indolyl position redirect the mode of cytotoxicity from methuosis to microtubule disruption. This switch in activity is associated with an increase in potency as large as 2 orders of magnitude. These compounds appear to represent a new class of potent microtubule-active anticancer agents.
