6659-45-6Relevant academic research and scientific papers
Preparation of rotenone derivatives and in vitro analysis of their antimalarial, antileishmanial and selective cytotoxic activities
Upegui, Yulieth,Gil, Juan F.,Quiones, Wiston,Torres, Fernando,Escobar, Gustavo,Robledo, Sara M.,Echeverri, Fernando
, p. 18911 - 18922 (2014)
Six derivatives of the known biopesticide rotenone were prepared by several chemical transformations. Rotenone and its derivatives showed differential in vitro antiparasitic activity and selective cytotoxicity. In general, compounds were more active against Plasmodium falciparum than Leishmania panamensis. Rotenone had an EC50 of 19.0 μM against P. falciparum, and 127.2 μM against L. panamensis. Although chemical transformation does not improve its biological profile against P. falciparum, three of its derivatives showed a significant level of action within an adequate range of activity with EC50 values 50 was >>400 μM. On the other hand, all derivatives displayed a non-specific cytotoxicity on several cell lines and primary human cell cultures.
Iron-Nickel Dual-Catalysis: A New Engine for Olefin Functionalization and the Formation of Quaternary Centers
Green, Samantha A.,Vásquez-Céspedes, Suhelen,Shenvi, Ryan A.
supporting information, p. 11317 - 11324 (2018/09/18)
Alkene hydroarylation forms carbon-carbon bonds between two foundational building blocks of organic chemistry: olefins and aromatic rings. In the absence of electronic bias or directing groups, only the Friedel-Crafts reaction allows arenes to engage alkenes with Markovnikov selectivity to generate quaternary carbons. However, the intermediacy of carbocations precludes the use of electron-deficient arenes, including Lewis basic heterocycles. Here we report a highly Markovnikov-selective, dual-catalytic olefin hydroarylation that tolerates arenes and heteroarenes of any electronic character. Hydrogen atom transfer controls the formation of branched products and arene halogenation specifies attachment points on the aromatic ring. Mono-, di-, tri-, and tetra-substituted alkenes yield Markovnikov products including quaternary carbons within nonstrained rings.
Hydromethylation of Unactivated Olefins
Dao, Hai T.,Li, Chao,Michaudel, Quentin,Maxwell, Brad D.,Baran, Phil S.
supporting information, p. 8046 - 8049 (2015/07/15)
A solution to the classic unsolved problem of olefin hydromethylation is presented. This highly chemoselective method can tolerate labile and reactive chemical functionalities and uses a simple set of reagents. An array of olefins, including mono-, di-, and trisubstituted olefins, are all smoothly hydromethylated. This mild protocol can be used to simplify the synthesis of a specific target or to directly "edit" complex natural products and other advanced materials. The method is also amenable to the simple installation of radioactive and stable labeled methyl groups.
Synthesis of 3H labeled dihydrorotenone
O'Neil, James P.,VanBrocklin, Henry F.,Morimoto, Hiromi,Williams, Philip G.
, p. 215 - 221 (2007/10/03)
The catalytic tritiation of rotenone results in the preparation of two products, the expected tritiated 6',7'-dihydrorotenone ([3H]DHR) and tritiated 6',7'-dihydrorotenol ([3H]DHR-ol). The ratio of [3H]DHR to [3H]DHR-ol is 9 to 1. Reversed-phase HPLC provided the purified [3H]DHR and [3H]DHR-ol with estimated specific activities of 45 and 60 Ci/mmol, respectively.
Regioselective Ether Cleavages of Rotenoids: Spiro-ether Formation and Stereoselective Isotopic Labelling of (E)- or (Z)-Phenyl Methyl Groups in (6aS, 12aS)-Rot-2'-enonic Acid
Carson, David,Crombie, Leslie,Kilbee, Geoffrey W.,Moffatt, Frank,Whiting, Donald A.
, p. 779 - 788 (2007/10/02)
Treated with boron tribromide (-)-(6aS,12aS,5'R)-rotenone is converted first into a primary allylic bromide by ring-E cleavage, then into the 2-de-O-methyl and finally the 2,3-dide-O-methyl derivatives.With (6aS,12aS,5'R)-6',7'-dihydrorotenone and (6aS,12aS)-isorotenone, ring-E cleavage does not take place.The main reaction is 2-, followed by 2,3-demethylation: this supports a stereospecific pericyclic mechanism for the rotenone ring-E cleavage.Treatment of the geometrically pure (E)-bromide with cyanoboro-deuteride or -tritide leads to (E)-4'-labelled (6aS,12aS)-rot-2'-enonic acid without reduction of the 12-carbonyl group.By using -rotenone, (E)-rot-2'-enonic acid is accessible.Trimethylsilyl iodide can cleave the 2-methoxy-group of rotenonewithout rupturing ring E, and remethylation with - or -diazomethane represents a convenient method for preparing a general tracer molecule.On treatment with sodium hydride, 3-de-O-methylisorotenone (but not the 2-isomer) rearranges into a spiroether, thus confirming the position of initial de-O-methylation as deduced from 1H and 13C n.m.r. data.Because of this rearrangement, methylenation (NaH-CH2I2) of 2,3-dide-O-methylisorotenone gives mainly the methylenedioxy-spiro-ether, with small yields of methylenedioxy-rotenoid.Deuteriogenolysis of (-)-rotenone over palladium catalyst in (2H5)pyridine gives (E)-rot-2'-enonic acid, but experiments using rotenone indicate stereoselectivity rather than stereospecificity, ca. 12percent of (Z)--accompanying the major (E)-product.A similar specimen of rotenonic acid has been prepared.A hydrogenolysis route from amorphigenin, via rotenone, to (Z)-rot-2'-enonic acid is described.
Evaluation of rotenone and related compounds as antagonists of slow-reacting substance of anaphylaxis
Ashack,McCarty,Malek,Goodman,Peet
, p. 1022 - 1026 (2007/10/02)
Rotenone, dihydrorotenone, isorotenone, mutarotenone, and deguelin were found to be potent antagonists of slow-reacting substance of anaphylaxis (SRS-A) in vitro. However, these compounds were also shown to inhibit histamine, serotonin, and acetylcholine
