19610-34-5Relevant academic research and scientific papers
Ortho-Carborane-Modified N-Substituted Deoxynojirimycins
Hoogendoorn, Sascha,Mock, Elliot D.,Strijland, Anneke,Donker-Koopman, Wilma E.,Van Den Elst, Hans,Van Den Berg, Richard J. B. H. N.,Aerts, Johannes M. F. G.,Van Der Marel, Gijsbert A.,Overkleeft, Herman S.
, p. 4437 - 4446 (2015)
N-alkyl-deoxynojirimycins (DNMs) are an important class of glycoprocessing enzyme inhibitors. Our work on DNMs focuses on identifying potent and selective inhibitors of the human enzymes, glucosylceramide synthase (GCS), lysosomal glucosylceramidase (GBA)
Modular synthetic approach to carboranyl-biomolecules conjugates
Feinhals, Alexander,Friedrichs, Jan-Simon Jeshua,Hey-Hawkins, Evamarie,Kellert, Martin,L?nnecke, Peter,Tepper, Jonas,Ullrich, Nadine Anke
, (2021)
The development of novel, tumor-selective and boron-rich compounds as potential agents for use in boron neutron capture therapy (BNCT) represents a very important field in cancer treatment by radiation therapy. Here, we report the design and synthesis of two promising compounds that combine meta-carborane, a water-soluble monosaccharide and a linking unit, namely glycine or ethylenediamine, for facile coupling with various tumor-selective biomolecules bearing a free amino or carboxylic acid group. In this work, coupling experiments with two selected biomolecules, a coumarin derivative and folic acid, were included. The task of every component in this approach was carefully chosen: the carborane moiety supplies ten boron atoms, which is a tenfold increase in boron content compared to the L-boronophenylalanine (L-BPA) presently used in BNCT; the sugar moiety compensates for the hydrophobic character of the carborane; the linking unit, depending on the chosen biomolecule, acts as the connection between the tumor-selective component and the boron-rich moiety; and the respective tumor-selective biomolecule provides the necessary selectivity. This approach makes it possible to develop a modular and feasible strategy for the synthesis of readily obtainable boron-rich agents with optimized properties for potential applications in BNCT.
Hydroxyl carborane derivative containing ether bond, and modified curing agent, preparation method and application thereof
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Paragraph 0051; 0054; 0057; 0060, (2021/07/14)
The invention discloses a hydroxyl carborane derivative containing an ether bond, a modified curing agent a preparation method and application of the hydroxyl carborane derivative. The structural formula of the hydroxyl carborane derivative containing the ether bond is one of the following formulas, wherein in the formula, an R1 group is -CH2CH2-, or an R3 group is -CH3, -CH2CH2CH3, -CH(CH3)2 and -CH2Ph. The preparation method comprises the following steps: carrying out hydroformylation on o-carborane to prepare o-carborane B-1 containing a single aldehyde group; carrying out reduction hydroxylation on the aldehyde group to prepare o-carborane B-2 containing a hydroxyl group; carrying out ring-opening reaction on the hydroxyl and epoxide to generate the hydroxyl carborane derivative containing the ether bond; and dropwise adding the derivative into an isocyanate curing agent for modification to obtain the modified curing agent. The finally obtained modified curing agent is longer in storage time, and an obtained paint film has the characteristics of high drying speed, strong flexibility and the like after the modified curing agent is mixed with resin.
Carborane containing phenylalanine compound, preparation method therefor and use of carborane containing phenylalanine compound
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Paragraph 0070; 0084-0087, (2019/08/12)
The invention discloses a carborane containing phenylalanine compound capable of being applied to boron neutron captured treatment, a preparation method therefor and use of the carborane containing phenylalanine compound. The compound disclosed by the inv
Method for regulating and controlling structure of o-carborane derivative through preoccupation
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Paragraph 0022; 0023, (2017/01/23)
The invention discloses a method for regulating and controlling the structure of an o-carborane derivative through preoccupation. The method comprises the following steps: (1) subjecting o-carborane to lithiation to form a monolithium salt and then reacting the monolithium salt with a CH group protecting agent so as to quantitatively convert the o-carborane into C-H protected carborane; (2) activating C-H by using butyllithium and then carrying out functionalization of a second carbon position; and (3) carrying out deprotection by using tetrabutyl ammonium fluoride. According to the invention, the CH group protecting agent is introduced at first, then the group is subjected to functionalization, and finally deprotection of the group is carried out, so the structure of the o-carborane derivative is regulated and controlled through preoccupation; and thus, a monosubstituted or disubstituted o-carborane derivative is purposefully and selectively synthesized. The obtained monosubstituted or disubstituted o-carborane derivative can be applied to field of aerospace materials like high-temperature-resistant bonding materials and composite materials and has great application prospect in the fields like biological medicines, catalysts, supramolecular systems and high energy fuels.
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+.
High yielding synthesis of carboranes under mild reaction conditions using a homogeneous silver(I) catalyst: Direct evidence of a bimetallic intermediate
El-Zaria, Mohamed E.,Keskar, Kunal,Genady, Afaf R.,Ioppolo, Joseph A.,McNulty, James,Valliant, John F.
supporting information, p. 5156 - 5160 (2014/05/20)
Methods used to prepare functionalized carboranes generally require heating to high temperatures, and thus limits the range of derivatives which can be prepared directly from alkynes. We show here that by using a homogeneous silver(I) catalyst it is now possible to prepare carboranes in good to excellent yield at temperatures below 40 °C, including at room temperature. The process is general and provides an important new synthetic strategy for the preparation of functionalized boron clusters. Cluster around: Current methods to prepare carboranes require heating to high temperatures, thereby limiting the range of derivatives which can be prepared from functionalized alkynes. By using a AgI catalyst it is possible to prepare carboranes from substituted alkynes in good to excellent yields at temperatures below 40 °C, including room temperature. The approach provides an important new synthetic strategy for the preparation of functionalized boron clusters.
High yielding preparation of dicarba-closo-dodecaboranes using a silver(I) mediated dehydrogenative alkyne-insertion reaction
Toppino, Antonio,Genady, Afaf R.,El-Zaria, Mohamed E.,Reeve, James,Mostofian, Fargol,Kent, Jeff,Valliant, John F.
supporting information, p. 8743 - 8749 (2013/09/02)
The synthesis of 1,2-dicarba-closo-dodecaboranes (ortho-carboranes) is often low yielding which is a critical issue given the increasing use of boron clusters in material science and medicinal chemistry. To address this barrier, a series of Cu, Ag, and Au salts were screened to identify compounds that would enhance the yields of ortho-caboranes produced when treating alkynes with B 10H12(CH3CN)2. Using a variety of functionalized ligands including mono- and polyfunctional internal and terminal alkynes, significant increases in yield were observed when AgNO3 was used in catalytic amounts. AgNO3 appears to prevent unwanted reduction/hydroboration of the alkyne prior to carborane formation, and the process is compatible with aryl, halo, hydroxy, nitrile, carbamate, and carbonyl functionalized alkynes.
Tetrabutylammonium fluoride promoted novel reactions of o- carborane: Inter- and intramolecular additions to aldehydes and ketones and annulation via enals and enones
Nakamura, Hiroyuki,Aoyagi, Kouichi,Yamamoto, Yoshinori
, p. 1167 - 1171 (2007/10/03)
The addition of o-carborane (1) to aldehydes 2 proceeded very smoothly in the presence of aqueous tetrabutylammonium fluoride (tbaf: 3 equiv) at room temperature, giving the corresponding carbinols 3 in high yeilds. The Tbaf-mediated reaction was appiled
