132509-41-2Relevant academic research and scientific papers
Synthesis and biological activities of new furo[3,4-b]carbazoles: Potential topoisomerase II inhibitors
Hajbi, Youssef,Neagoie, Cléopatra,Biannic, Bérenger,Chilloux, Aurélie,Vedrenne, Emeline,Baldeyrou, Brigitte,Bailly, Christian,Mérour, Jean-Yves,Rosca, Sorin,Routier, Sylvain,Lansiaux, Amélie
experimental part, p. 5428 - 5437 (2010/12/25)
New 1,5-Dihydro-4-(substituted phenyl)-3H-furo[3,4-b]carbazol-3-ones were synthesised via a key step Diels-Alder reaction under microwave irradiation. 3-Formylindole was successfully used in a 6-step synthesis to obtain those complex heterocycles. The Diels-Alder reaction generating the carbazole ring was optimised under thermal conditions or microwave irradiation. After cleavage of functional groups, DNA binding, topoisomerase inhibition and cytotoxic properties of the new-formed furocarbazoles were investigated. These carbazoles do not present a strong interaction with the DNA, and do not modify the relaxation of the DNA in the presence of topoisomerase I or II except for one promising compound. This compound is a potent topoisomerase II inhibitor, and its cellular activity is not moderated compared to etoposide. The synthesis of these molecules allowed the generalisation of the method using indole and 5-OBn indole and several benzaldehydes. The synthesis of these molecules produced chemical structures endowed with promising cytotoxic and topoisomerase II inhibition activities.
Palladium-catalyzed coupling of 3-indolyl triflate. Syntheses of 3-vinyl and 3-alkynylindoles
Gribble,Conway
, p. 2129 - 2141 (2007/10/02)
Palladium-catalyzed coupling of 1-(phenylsulfonyl)indol-3-yl trifluoromethanesulfonate (triflate) (1) with terminal alkenes and alkynes gives 3-vinyl (2) and 3-alkynylindoles in 45-93% yields. An attempt to generate 2,3-indolyne 22 from 2-trimethylsilyl-3-indolyl triflate 20 gives indigo (23).
