208347-68-6Relevant academic research and scientific papers
Diastereodivergent Reductive Cross Coupling of Alkynes through Tandem Catalysis: Z- and E-Selective Hydroarylation of Terminal Alkynes
Armstrong, Megan K.,Goodstein, Madison B.,Lalic, Gojko
supporting information, p. 10233 - 10241 (2018/08/23)
A diastereodivergent hydroarylation of terminal alkynes is accomplished using tandem catalysis. The hydroarylation allows highly selective synthesis of both E and Z diastereoisomers of aryl alkenes, from the same set of starting materials, using the same combination of palladium and copper catalysts. The selectivity is controlled by simple changes in the stoichiometry of the alcohol additive. The hydroarylation has excellent substrate scope and can be accomplished in the presence of various classes of compounds, including esters, nitriles, alkyl halides, epoxides, carbamates, acetals, ethers, silyl ethers, and thioethers. The Z-selective hydroarylation is accomplished using a new approach based on tandem Sonogashira coupling and catalytic semireduction. The E-selective hydroarylation involves an additional catalytic isomerization of the Z-alkene. Our explorations of the reaction mechanism explain the role of individual reaction components and how the subtle changes in the reaction conditions influence the rates of specific steps of the hydroarylation. Our studies also show that, although the Z- and E-selective hydroarylation reactions are mechanistically closely related, the roles of the palladium and copper catalysts in the two reactions are different.
Synthesis and antiproliferative activity of conformationally restricted 1,2,3-triazole analogues of combretastatins in the sea urchin embryo model and against human cancer cell lines
Demchuk, Dmitry V.,Samet, Alexander V.,Chernysheva, Natalia B.,Ushkarov, Vladimir I.,Stashina, Galina A.,Konyushkin, Leonid D.,Raihstat, Mikhail M.,Firgang, Sergei I.,Philchenkov, Alex A.,Zavelevich, Michael P.,Kuiava, Ludmila M.,Chekhun, Vasyl F.,Blokhin, Dmitry Yu.,Kiselyov, Alex S.,Semenova, Marina N.,Semenov, Victor V.
, p. 738 - 755 (2014/01/23)
A series of 1,5-diaryl- and 4,5-diaryl-1,2,3-triazole derivatives of combretastatin A4 were synthesized and evaluated as antimitotic microtubule destabilizing agents using the sea urchin embryo model. Structure-activity relationship studies identified compounds substituted with 3,4,5- trimethoxyphenyl and 3,4-methylenedioxy-5-methoxyphenyl ring A and 4-methoxyphenyl ring B as potent antiproliferative agents with high cytotoxicity against a panel of human cancer cell lines including multi-drug resistant cells. 4,5-Diaryl-1,2,3-triazoles (C-C geometry) were found to be considerably more active than the respective 1,5-diaryl-1,2,3-triazoles (N-C geometry). Compound 10ad′ induced G2/M cell cycle arrest and apoptosis in human T-leukemia Jurkat cells via caspase 2/3/9 activation and downregulation of the antiapoptotic protein XIAP. A mitotic catastrophe has been evaluated as another possible cell death mode.
Diaryl-substituted ortho-carboranes as a new class of hypoxia inducible factor-1α inhibitors
Nakamura, Hiroyuki,Tasaki, Lisa,Kanoh, Daisuke,Sato, Shinichi,Ban, Hyun Seung
, p. 4941 - 4944 (2014/04/03)
Diaryl-substituted ortho-carboranes 1 were synthesized from the corresponding alkynes by decaborane coupling under microwave-irradiated conditions with a combination of N,N-dimethylaniline and chlorobenzene. Among the compounds synthesized, 1a and 1d exhibited significant inhibition of hypoxia-induced HIF-1 transcriptional activity. Both compounds similarly suppressed hypoxia-induced HIF-1α accumulation in a concentration- dependent manner without affecting HIF-1α mRNA expression.
Iron-catalyzed cross-coupling between 1-bromoalkynes and grignard-derived organocuprate reagents
Castagnolo, Daniele,Botta, Maurizio
supporting information; experimental part, p. 3224 - 3228 (2010/08/20)
An efficient iron-catalyzed cross-coupling reaction between alkynyl bromides and Grignard-derived organocuprates has been developed. A series of alkynylarenes were successfully synthesised by starting from different 1-bromoalkynes and Grignard reagents. The methodology was successfully used for the two-step stereoselective synthesis of combretastatins and represents a valid alternative to the classical syntheses of alkynylarenes.
Preparation and evaluation of diarylalkynes as antitumour agents
Hadfield, John A.,McGown, Alan T.
, p. 1421 - 1431 (2007/10/03)
A series of diarylalkynes have been synthesised and tested for anti- tumour activity.
