- N,O-Iminoboronates: Reversible Iminoboronates with Improved Stability for Cancer Cells Targeted Delivery
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Herein a new class of iminoboronates obtained from 2-acetylbenzene boronic acids and aminophenols is presented. The N,O-ligand topology enabled the formation of an additional B?O bond that locks the boron center in a tetrahedral geometry. This molecular arrangement decisively contributes to improve the construct′s stability in biocompatible conditions and retaining the iminoboronate reversibility in more acidic environments. 2-Acetylbenzene boronic acid was reacted with a fluorescent amino-coumarin to yield a stable and non-fluorescent N,O-iminoboronate. This mechanism was further used to assemble a folate receptor targeting conjugate that selectively delivered the fluorescent amino-coumarin to MDA-MB-231 human breast cancer cells.
- Lopes, Ricardo M. R. M.,Ventura, Ana E.,Silva, Liana C.,Faustino, Hélio,Gois, Pedro M. P.
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- Transition metal complex and application thereof
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The invention relates to a transition metal complex and application thereof. The transition metal complex has a structural general formula shown as chemical formula (1). The transition metal complex is used as a light-emitting layer doping material, and c
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Paragraph 0191; 0201-0203
(2020/02/14)
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- Tris(2-carboxyethyl)phosphine promotes hydrolysis of iminoboronates
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Iminoboronates are stable and formed fast. Their B[sbnd]N bonds could be reverted by some endogenous biological molecules. The reversible characteristic attracts significant attention in biological and chemical fields. Although synthesis of iminoboronates is well-studied, less efforts have been devoted to disconnecting the units. Here, a series of selected compounds were screened to evaluate their hydrolytic capability of iminoboronates by 1H NMR or 11B NMR detection. Tris(2-carboxyethyl)phosphine (TCEP), was emerged as an excellent reagent, which decomposed most iminoboronates in short time with high yields. In addition, TCEP is also able to hydrolyze hydrazones and oximes with moderate yields.
- Liu, Xiaoyu,Li, Zhihong,Xu, Hongtao,Zhan, Yuexiong,Ma, Peixiang,Chen, Hongli,Jiang, Biao
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p. 3101 - 3106
(2017/07/18)
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- Synthesis of naphthalene ring derivatives and Benzoheterocycles the method of the compound
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The invention discloses a method for synthesizing naphthalene derivative and benzo-heterocycle compounds. The method is realized by promoting a reaction similar to Mortia-Baylis-Hillman between aryl aldehyde having alpha, beta-unsaturated ester on ortho-position and ketone compounds under the catalysis action of tertiary amine and tertiary phosphine organic small molecular catalysts, so as to remove a molecule of H2O, so that the naphthalene derivative or benzo-heterocycle compounds are generated. The method disclosed by the invention is simple in operation step, cheap and easily available in adopted catalysts and harmless to environment, and a series of naphthalene derivative and benzo-heterocycle compounds are synthesized with relatively high yield.
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Paragraph 0034; 0035
(2016/10/10)
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- Iminoboronate Formation Leads to Fast and Reversible Conjugation Chemistry of α-Nucleophiles at Neutral pH
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Bioorthogonal reactions that are fast and reversible under physiological conditions are in high demand for biological applications. Herein, it is shown that an ortho boronic acid substituent makes aryl ketones rapidly conjugate with α-nucleophiles at neutral pH. Specifically, 2-acetylphenylboronic acid and derivatives were found to conjugate with phenylhydrazine with rate constants of 102 to 103M-1s-1, comparable to the fastest bioorthogonal conjugations known to date. 11BNMR analysis revealed the varied extent of iminoboronate formation of the conjugates, in which the imine nitrogen forms a dative bond with boron. The iminoboronate formation activates the imines for hydrolysis and exchange, rendering these oxime/hydrazone conjugations reversible and dynamic under physiological conditions. The fast and dynamic nature of the iminoboronate chemistry should find wide applications in biology.
- Bandyopadhyay, Anupam,Gao, Jianmin
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supporting information
p. 14748 - 14752
(2015/10/19)
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- Scope of the palladium-catalyzed aryl borylation utilizing bis-boronic acid
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The Suzuki-Miyaura reaction has become one of the more useful tools for synthetic organic chemists. Until recently, there did not exist a direct way to make the most important component in the coupling reaction, namely the boronic acid. Current methods to make boronic acids often employ harsh or wasteful reagents to prepare boronic acid derivatives and require additional steps to afford the desired boronic acid. The scope of the previously reported palladium-catalyzed, direct boronic acid synthesis is unveiled, which includes a wide array of synthetically useful aryl electrophiles. It makes use of the newly available second generation Buchwald XPhos preformed palladium catalyst and bis-boronic acid. For ease of isolation and to preserve the often sensitive C-B bond, all boronic acids were readily converted to their more stable trifluoroborate counterparts.
- Molander, Gary A.,Trice, Sarah L. J.,Kennedy, Steven M.,Dreher, Spencer D.,Tudge, Matthew T.
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supporting information; experimental part
p. 11667 - 11673
(2012/09/05)
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- Deprotection of pinacolyl boronate esters by transesterification with polystyrene-boronic acid
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A mild, efficient method for the deprotection of pinacolyl organoboronate esters is described. Treatment of the organoboronate ester with excess polystyrene-boronic acid followed by filtration and evaporation of the solvent provides the corresponding organoboronic acid. Mild deprotection of pinacolyl boronate esters to the corresponding boronic acids was achieved in the presence of excess polystyrene-boronic acid via a transesterification process. The procedure allows for the cleavage of pinacolyl boronate esters in the presence of sensitive functional groups. Crown Copyright
- Pennington, Thomas E.,Kardiman, Cynantya,Hutton, Craig A.
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p. 6657 - 6660
(2007/10/03)
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- Structure and spectroscopic characteristics of 2'-diethylboryl-4''- dimethylaminochalcone bearing an intramolecular boron-oxygen coordinate bond
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How formation of an intramolecular coordinate bond affects the molecular structure was examined in the structural comparison of 2'-diethylboryl-4''- dimethylaminochalcone (1) and 2'-ethylenedioxyboryl-4''-dimethylaminochalcone (2) with chloro-{2-[(4-dimethylaminostyryl) carbonyl] phenyl} (4-methyl- phenyl)] bismuthane (3) and 4''-dimethylaminochalcone (4).
- Murafuji,Sugihara,Moriya,Mikata,Yano
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p. 683 - 685
(2008/10/08)
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