Progress in the medicinal chemistry of organoboron compounds

Tevyashova, Anna N.; Chudinov, M. V.

doi:10.1070/rcr4977

Cited by 25 publications

(15 citation statements)

References 214 publications

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“…This broadspectrum activity of diazaborine compounds highlights its high therapeutic potential. Over years, there has been an continuous effort of synthesizing and evaluating new classes of diazaborines for different purposes 57 . There are several types of diazaborines, including benzene, naphthalene, thiophene, furan and pyrrole.…”

Section: Discussionmentioning

confidence: 99%

Structural dynamics of AAA+ ATPase Drg1 and mechanism of benzo-diazaborine inhibition

Gao

et al. 2022

Preprint

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The AAA+ ATPase Drg1 is a ribosome assembly factor in yeast, and functions to release Rlp24, another assembly factor, from the pre-60S particle just exported from nucleus to initiate its further cytoplasmic maturation. Being a type II AAA+ protein with two ATPase domains (D1 and D2), its activity in ribosome assembly can be inhibited by a drug molecule diazaborine. In human, mutations of Drg1 homologue has been linked to a disease condition called epilepsy, hearing loss, and mental retardation syndrome. Although the general structure of Drg1 hexamer was recently reported, its complete structure and dynamic conformational rearrangements driven by ATP-hydrolysis are poorly understood. Here, we report a comprehensive structural characterization of Drg1 hexamers in different nucleotide-binding and benzo-diazaborine treated states. Our data show that Drg1 hexamers transits between two extreme conformations, characterized by a planar or helical arrangement of its six protomers. By forming covalent adducts with the ATP molecules in the active centers of both D1 and D2, benzo-diazaborine locks Drg1 hexamers in a more symmetric and non-productive conformation. In addition, we obtained the structure of a mutant Drg1 hexamer (Walker B mutations) with a polypeptide trapped in the central channel, representing a 3D snapshot of its functional, substrate-processing form. Conserved pore loops on the ATPase domains of Drg1 form a spiral staircase to interact with the substrate through a sequence-independent manner. These results suggest that Drg1, similar as Cdc48/p97, acts as a molecular unfoldase to remodel pre-60S particles, and benzo-diazaborine inhibits both the inter-protomer and inter-ring communication to disable the conformational cycling of Drg1 protomers required for the unfolding activity.

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Section: Discussionmentioning

confidence: 99%

Structural dynamics of AAA+ ATPase Drg1 and mechanism of benzo-diazaborine inhibition

Gao

et al. 2022

Preprint

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“…Yield: 2.63 g (91%). MP (EtOH) 75.7-78.0 C; 1 47 Synthesis of 1-(3,4-dimethoxyphenyl)-N-(4-tetradecylphenyl) methanimine (13). General procedure 1 was followed using 4tetradecylaniline (1.74 g, 6.02 mmol) and 3,4-dimethoxybenzaldehyde (1.00 g, 6.02 mmol) to give the title compound as a colourless solid.…”

Section: Methodsmentioning

confidence: 99%

“…Yield: 0.210 g (61%). (br s, 2H), 1.38-1.30 (m, 2H), 1.21-1.16 (m, 20H), 0.73 (t, 2H, J ¼ 7.8 Hz) ppm; 13 (33). General procedure 7 was followed using [Ir(COD)Cl] 2 (0.008 g, 0.01 mmol) and dppm (0.008 g, 0.02 mmol) in THF (2 mL), 29 (0.100 g, 0.229 mmol) in THF (1 mL), and HBPin (0.080 mL, 0.550 mmol) in THF (1 mL) to provide the product as a yellow oil.…”

Section: Methodsmentioning

confidence: 99%

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Boron-containing capsaicinoids

et al. 2021

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“…The addition reaction of diborons with olefin is an effective method to obtain organoboron compounds [ 1 , 2 , 3 ]. Organoboronic acid compounds are important intermediates in drug molecules and organic synthesis, where C-B bonds could be converted into C-C, C-H, and C-O bonds by simple reactions [ 4 , 5 , 6 ]. Therefore, the efficient construction of carbon–boron bonds, especially the synthesis of chiral organoboronic acid compounds, has been a hot topic of interest for researchers.…”

Section: Introductionmentioning

confidence: 99%

Copper Foam as Active Catalysts for the Borylation of α, β-Unsaturated Compounds

Zheng

Liu

Meng

et al. 2022

IJMS

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The use of simple, inexpensive, and efficient methods to construct carbon–boron and carbon–oxygen bonds has been a hot research topic in organic synthesis. We demonstrated that the desired β-boronic acid products can be obtained under mild conditions using copper foam as an efficient heterogeneous catalyst. The structure of copper foam before and after the reaction was investigated by polarized light microscopy (PM), scanning electron microscopy (SEM), and transmission electron microscopy (TEM), and the results have shown that the structure of the catalyst copper foam remained unchanged before and after the reaction. The XPS test results showed that the Cu(0) content increased after the reaction, indicating that copper may be involved in the boron addition reaction. The specific optimization conditions were as follows: CH3COCH3 and H2O were used as mixed solvents, 4-methoxychalcone was used as the raw material, 8 mg of catalyst was used and the reaction was carried out at room temperature and under air for 10 h. The yield of the product obtained was up to 92%, and the catalytic efficiency of the catalytic material remained largely unchanged after five cycles of use.

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Progress in the medicinal chemistry of organoboron compounds

Cited by 25 publications

References 214 publications

Structural dynamics of AAA+ ATPase Drg1 and mechanism of benzo-diazaborine inhibition

Structural dynamics of AAA+ ATPase Drg1 and mechanism of benzo-diazaborine inhibition

Boron-containing capsaicinoids

Copper Foam as Active Catalysts for the Borylation of α, β-Unsaturated Compounds

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