53257-04-8Relevant academic research and scientific papers
On the reactions of haloidmagnesiummethyl-m-carboranes with organoalkoxysilanes and chlorosilanes
Izmaylov, Boris A.,Vasnev, Valerii A.,Markova, Galy D.
, p. 475 - 480 (2017/12/07)
For the first time an effective method for the preparation of 1-methoxy(dimethyl)silylmethyl-m-carborane and 1,7-bis[chloro(dimethyl)silylmethyl]-m-carborane using 1-haloidmagnesiummethyl-m-carborane and 1,7-bis[haloidmagnesiummethyl]-m-carborane was developed. It has been established that in the course of the reaction of 1-haloidmethyl-m-carboranes with magnesium both in ether and THF, simultaneously with the formation of 1-haloidmagnesiummethyl-m-carborane – the resulting Grignard reagent, proceeds the isomerization of carborane products and their remetallization with the obtained Grignard reagent. This leads to the formation of a complex mixture of products and the decrease in the yield of the resulting Grignard reagent to 43–67%. It has been shown that by using 1-haloidmethyl-m-carboranes substituted in the second carbon atom, for example, 1,7-bis[bromomethyl]-m-carborane, in the reactions for obtaining Grignard reagents, it is possible to eliminate the isomerization of carborane products and their remetallization with the target Grignard reagent 1,7-bis[bromomagnesiummethyl]-m-carborane in 90% yield.
Improved synthesis of MC4-PPEA and the biological evaluation of its hydroxymethyl derivative
Sadrerafi, Keivan,Zargham, Emilia O.,Lee, Mark W.
supporting information, p. 618 - 621 (2016/01/09)
Nicotinamide phosphoribosyltransferase (Nampt) is an intriguing target for the treatment of many diseases, including cancer. Previously, our group demonstrated that carborane clusters may be used to increase the potency of small molecule inhibitors of Nam
11B NMR Probes of Copper(II): Finding and Implications of the Cu2+-Promoted Decomposition of ortho-Carborane Derivatives
Tanaka, Tomohiro,Nishiura, Yukiko,Araki, Rikita,Saido, Takaomi,Abe, Ryo,Aoki, Shin
, p. 1819 - 1834 (2016/05/02)
The development of noninvasive methodologies for the detection of d-block metal ions such as copper (Cu2+), zinc (Zn2+), and manganese (Mn2+) is important for understanding their biological roles and relationship with diseases. We have been interested in the use of 11B NMR probes for the detection of d-block metal ions, because 11B is an ultratrace element in living systems. o-Carboranes, which consist of ten boron and two carbon atoms, have been applied to numerous drugs and biological active agents. In this work, we found that the o-carborane-pendant cyclens (L3-L5) (cyclen = 1,4,7,10-tetraazacyclododecane) are decomposed in the presence of Mn2+ or Cu2+ in aqueous solution at neutral pH, accompanied by the release of 4-9 equiv. of B(OH)3. Furthermore, it was found that o-carborane derivatives that contain hydroxyl groups instead of a cyclen unit also undergo decomposition in the presence of Cu2+ and the corresponding complexes such as Cu(bpy) to afford 10 equiv. of B(OH)3, as confirmed by 11B NMR spectroscopic analysis and an azomethine-H assay. These reactions are applied to 11B MRI (magnetic resonance imaging) probes for Cu2+.
