Synthesis of maleimide-functionalized carboranes and their utility in Michael addition reactions

Ol’shevskaya, V. A.; Alpatova, Victoria M.; Makarenkov, Anton V.; Kononova, Elena G.; Smol’yakov, Alexander F.; Peregudov, Аlexander S.; Rys, E. G.

doi:10.1039/d1nj02499j

Cited by 4 publications

(4 citation statements)

References 41 publications

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“…The reactions were carried out in CH 2 Cl 2 in the presence of Et 3 N ( Scheme 4 ) to afford the acylated derivatives 11 and 12 in 63 and 85% yield, respectively. It is known [ 42 – 43 ] that maleimido-substituted compounds readily enter reactions with thiols to generate thiosuccinimide products and meanwhile this method has become one of the most popular route for the site-selective modification of cysteine residues in bioconjugation technology. We suppose that the maleimide group in porphyrin 11 is a useful target for thiol conjugation via Michael addition reactions [ 44 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of new representatives of A₃B-type carboranylporphyrins based on meso-tetra(pentafluorophenyl)porphyrin transformations

Alpatova,

Rys,

Kononova

et al. 2024

Beilstein J. Org. Chem.

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A carboranylporphyrin of A3B-type bearing a single pentafluorophenyl ring was prepared through the regioselective nucleophilic aromatic substitution reaction of the p-fluorine atoms in 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin with 9-mercapto-m-carborane. The reaction of this porphyrin with sodium azide led to the selective substitution of the p-fluorine atom in the pentafluorophenyl substituent with an azide functionality which upon reduction with SnCl2 resulted in the formation of the corresponding porphyrin with an amino group. Pentafluorophenyl-substituted A3B-porphyrins were studied and transformed to thiol and amino-substituted compounds allowing for the preparation of porphyrins with different reactive groups such as hydroxy and amino derivatives capable for further functionalization and conjugation of these porphyrins to other substrates. In addition, conjugates containing maleimide or biotin entities in the structure of carborane A3B-porphyrin were also synthesized based on the amino-substituted A3B-porphyrin. The structures of the prepared carboranylporphyrins were determined by UV–vis, IR, 1H, 19F, 11B NMR spectroscopic data and MALDI mass spectrometry.

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Section: Resultsmentioning

confidence: 99%

Synthesis of new representatives of A₃B-type carboranylporphyrins based on meso-tetra(pentafluorophenyl)porphyrin transformations

Alpatova,

Rys,

Kononova

et al. 2024

Beilstein J. Org. Chem.

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“…In light of maleimides importance in medicinal chemistry, conjugates 24 , 25 containing a carboranylmaleimide fragments have been obtained by the reaction of phenylenediamine-substituted porphyrin 26 (prepared from conjugate 3 and 1,4-phenylenediamine 27 ) with 3-bromo-1-( N -( o -carborane-3′-yl)maleimide ( 28 ) [ 67 ] ( Scheme 7 ). This reaction resulted in the formation of two products.…”

Section: Resultsmentioning

confidence: 99%

Multicomponent Molecular Systems Based on Porphyrins, 1,3,5-Triazine and Carboranes: Synthesis and Characterization

et al. 2022

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2,4,6-Trichloro-1,3,5-triazine (cyanuric chloride) is an excellent coupling reagent for the preparation of highly structured multifunctional molecules. Three component systems based on porphyrin, cyanuric chloride and carborane clusters were prepared by a one-pot stepwise amination of cyanuric chloride with 5-(4-aminophenyl)-10,15,20-triphenylporphyrin, followed by replacement of the remaining chlorine atoms with carborane S- or N-nucleophiles. Some variants of 1,3,5-triazine derivatives containing porphyrin, carborane and residues of biologically active compounds such as maleimide, glycine methyl ester as well as thioglycolic acid, mercaptoethanol and hexafluoroisopropanol were also prepared. A careful control of the reaction temperature during the substitution reactions will allow the synthesis of desired compounds in a good to high yields. The structures of synthesized compounds were determined with UV-vis, IR, 1H NMR, 11B NMR, MALDI-TOF or LC-MS spectroscopic data. The dark and photocytotoxicity as well as intracellular localization and photoinduced cell death for compounds 8, 9, 17, 18 and 24 were evaluated.

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“…In particular, considerable attention is paid to the preparation of carborane-containing derivatives and analogues of natural amino acids and short peptides [18][19][20][21][22][23][24][25].…”

Section: Of 14mentioning

confidence: 99%

“…the introduction of boron-containing groups (fragments of boric acid or polyhedral boranes and carboranes) into the structure of natural compounds that can be selectively absorbed by tumour cells [16,17]. In particular, considerable attention is paid to the preparation of carborane-containing derivatives and analogues of natural amino acids and short peptides [18][19][20][21][22][23][24][25].…”

Section: Synthesismentioning

confidence: 99%

Carborane-Containing Folic Acid bis-Amides: Synthesis and In Vitro Evaluation of Novel Promising Agents for Boron Delivery to Tumour Cells

Gruzdev

Telegina

Левит

et al. 2022

IJMS

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The design of highly selective low-toxic, low-molecular weight agents for boron delivery to tumour cells is of decisive importance for the development of boron neutron capture therapy (BNCT), a modern efficient combined method for cancer treatment. In this work, we developed a simple method for the preparation of new closo- and nido-carborane-containing folic acid bis-amides containing 18–20 boron atoms per molecule. Folic acid derivatives containing nido-carborane residues were characterised by high water solubility, low cytotoxicity, and demonstrated a good ability to deliver boron to tumour cells in in vitro experiments (up to 7.0 µg B/106 cells in the case of U87 MG human glioblastoma cells). The results obtained demonstrate the high potential of folic acid–nido-carborane conjugates as boron delivery agents to tumour cells for application in BNCT.

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Synthesis of maleimide-functionalized carboranes and their utility in Michael addition reactions

Abstract: Carboranyl maleimides were obtained and their reactivity with S- and N-nucleophiles was demonstrated.

Cited by 4 publications

References 41 publications

Synthesis of new representatives of A₃B-type carboranylporphyrins based on meso-tetra(pentafluorophenyl)porphyrin transformations

Synthesis of new representatives of A₃B-type carboranylporphyrins based on meso-tetra(pentafluorophenyl)porphyrin transformations

Multicomponent Molecular Systems Based on Porphyrins, 1,3,5-Triazine and Carboranes: Synthesis and Characterization

Carborane-Containing Folic Acid bis-Amides: Synthesis and In Vitro Evaluation of Novel Promising Agents for Boron Delivery to Tumour Cells

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Synthesis of maleimide-functionalized carboranes and their utility in Michael addition reactions

Abstract: Carboranyl maleimides were obtained and their reactivity with S- and N-nucleophiles was demonstrated.

Cited by 4 publications

References 41 publications

Synthesis of new representatives of A3B-type carboranylporphyrins based on meso-tetra(pentafluorophenyl)porphyrin transformations

Synthesis of new representatives of A3B-type carboranylporphyrins based on meso-tetra(pentafluorophenyl)porphyrin transformations

Multicomponent Molecular Systems Based on Porphyrins, 1,3,5-Triazine and Carboranes: Synthesis and Characterization

Carborane-Containing Folic Acid bis-Amides: Synthesis and In Vitro Evaluation of Novel Promising Agents for Boron Delivery to Tumour Cells

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Synthesis of new representatives of A₃B-type carboranylporphyrins based on meso-tetra(pentafluorophenyl)porphyrin transformations

Synthesis of new representatives of A₃B-type carboranylporphyrins based on meso-tetra(pentafluorophenyl)porphyrin transformations