73252-59-2Relevant academic research and scientific papers
Synthesis of o-Deuterio- and o-Halogeno-acetophenones via Oxidation of η2-(2-Acetylphenyl)tetracarbonylmanganese Derivatives and the Determination of a Primary Kinetic Isotope Effect in ortho-Metallation of Acetophenones
Gommans, Louie H. P.,Main, Lyndsay,Nicholson, Brian K.
, p. 12 - 13 (1986)
2'-Deuterioacetophenone and 2'-deuterio-3',4',5'-trimethoxyacetophenone are obtained by reaction of the corresponding η2-(2-acetylphenyl)tetracarbonylmanganese compounds with cerium(IV) ammonium nitrate in CD3CO2D while 2'-iodo- and 2'-bromo-3'
Efficient Synthesis of Glaziovianin A Isoflavone Series from Dill and Parsley Extracts and Their in Vitro/in Vivo Antimitotic Activity
Semenov, Victor V.,Tsyganov, Dmitry V.,Semenova, Marina N.,Chuprov-Netochin, Roman N.,Raihstat, Mikhail M.,Konyushkin, Leonid D.,Volynchuk, Polina B.,Marusich, Elena I.,Nazarenko, Vera V.,Leonov, Sergey V.,Kiselyov, Alex S.
, p. 1429 - 1438 (2016/06/09)
A concise six-step protocol for the synthesis of isoflavone glaziovianin A (GVA) and its alkoxyphenyl derivatives 9 starting with readily available plant metabolites from dill and parsley seeds was developed. The reaction sequence involved an efficient conversion of the key intermediate epoxides 7 into the respective β-ketoaldehydes 8 followed by their Cu(I)-mediated cyclization into the target series 9. The biological activity of GVA and its derivatives was evaluated using a panel of seven human cancer cell lines and an in vivo sea urchin embryo assay. Both screening platforms confirmed the antimitotic effect of the parent GVA (9cg) and its alkoxy derivatives. Structure-activity relationship studies suggested that compounds 9cd and 9cf substituted with trimethoxy- and dillapiol-derived B-rings, respectively, were less active than the parent 9cg. Of the evaluated human cancer cell lines, the A375 melanoma cell line was the most sensitive to the tested molecules. Notably, the target compounds were not cytotoxic against human peripheral blood mononuclear cells up to 10 μM concentration. Phenotypic readouts from the sea urchin assay unequivocally suggest a direct microtubule-destabilizing effect of isoflavones 9cg, 9cd, and 9cf.
Synthesis, biological evaluation, and structure-activity relationships of tri- and tetrasubstituted olefins related to isocombretastatin A-4 as new tubulin inhibitors
Aziz, Jessy,Brachet, Etienne,Hamze, Abdallah,Peyrat, Jean-Fran?ois,Bernadat, Guillaume,Morvan, Estelle,Bignon, Jér?me,Wdzieczak-Bakala, Joanna,Desravines, Déborah,Dubois, Joelle,Tueni, Marie,Yassine, Ahmad,Brion, Jean-Daniel,Alami, Mouad
, p. 430 - 442 (2013/02/23)
The synthesis and structure-activity relationships associated with a series of 1,1-diarylethylene tubulin polymerization inhibitors 3 and 4 are described. The key step for their preparation involves a palladium-catalyzed coupling of N-arylsulfonylhydrazon
A General SRN1-Based Method for Total Synthesis of Unsymmetrically Hydroxylated 2,2'-Binaphtalenes
Beugelmans, Rene,Bois-Choussy, Michele,Tang, Qian
, p. 3880 - 3883 (2007/10/02)
An SRN1 reaction between 2'-haloacetophenones and 2'-acetonaphthone derived enolates is the key step in a straightforward one-pot synthesis of unsymetrically substituted 2,2'-binaphtyl derivatives 3a-j.
The Ambient Temperature Ullmann Reaction and Its Application to the Total Synthesis of (+/-)-Steganacin
Ziegler, Frederick E.,Chliwner, Irene,Fowler, Kerry W.,Kanfer, Sheldon J.,Kuo, Stephen J.,Sinha, Nanda D.
, p. 790 - 798 (2007/10/02)
The details of a new method for preparing unsymmetrical biphenyls at room temperature by a modification of the classical Ullmann reaction are discussed.An intramolecularly coordinated organocopper reagent is treated with an aryl iodide bearing a potential coordinating ligand to form the biphenyl.Nitrogen and sulfur have been utilized as ligands and as protecting groups for carbonyls.The application of this methodology to the synthesis of the antileukemic steganacin is detailed.
