128009-30-3Relevant academic research and scientific papers
Pentafluorophenyl Substitution of Natural Di(indol-3-yl)methane Strongly Enhances Growth Inhibition and Apoptosis Induction in Various Cancer Cell Lines
Ahmad, Aamir,Dandawate, Prasad,Schruefer, Sebastian,Padhye, Subhash,Sarkar, Fazlul H.,Schobert, Rainer,Biersack, Bernhard
, (2019)
Di(indol-3-yl)methane (=3,3′-methanediyldi(1H-indole), DIM, 1) is a known weakly antitumoral compound formed by digestion of indole-3-carbinol (=1H-indol-3-ylmethanol), an ingredient of various Brassica vegetables. Out of a series of nine fluoroaryl deriv
Utilization of flow chemistry in catalysis: New avenues for the selective synthesis of Bis(indolyl)methanes
Mohapatra, Swapna S.,Wilson, Zoe E.,Roy, Sujit,Ley, Steven V.
, p. 1812 - 1819 (2017/03/11)
Flow chemistry enables the preparation of bis(indolyl)methanes from various indoles and structurally divergent aldehydes using Sc(OTf)3 catalysis. The reaction is regioselective for C-3 functionalization of the indoles, occurring over short reaction times allowing for rapid investigation of scope with straightforward work up facilitating product isolation.
SYNTHESIS OF 1-(PENTAFLUOROPHENYL)-β-CARBOLINE
Fujii, Shozo,Kimoto, Hiroshi,Nishida, Masakazu,Cohen, Louis A.
, p. 479 - 489 (2007/10/02)
Thermal condensation of tryptamine with pentafluorobenzaldehyde in ethanol afforded 1-(pentafluorophenyl)-1,2,3,4-tetrahydro-β-carboline (I, 51percent yield), together with two byproducts (IIa, 9percent yield and IIb, 14percent yield) which were produced by nucleophilic substitution of an aromatic fluorine atom by the tryptamine amino group.In solvent acetic acid, the same reactants gave 2-acetyl-1-(pentafluorophenyl)-1,2,3,4-tetrahydro-β-carboline (III, 64percent yield) as the main product, together with a reduced yield (20percent) of I.Dehydrogenation of I with selenium dioxide provided 1-(pentafluorophenyl)-β-carboline (IV) in 84percent yield; III also gave IV in 72percentyield.Partial dehydrogenation of I with potassium permanganate provided 1-(pentafluorophenyl)-3,4-dihydro-β-carboline (V, 80percent yield) but V could not be obtained from III.Indole itself provided (pentafluorophenyl)bis(3-indolyl)methane (VI, 82percent yield) by simple reflux with pentafluorobenzaldehyde in propanol.In solvent acetic acid, the yield of VI was 78percent.
