Synthesis of ortho-modified mercapto- and piperazino-methyl-phenylboronic acid derivatives

Spencer, John; Burd, Andrew; Goodwin, Christopher A.; Merette, Sandrine; Scully, Michael; Adatia, Trushar; Deadman, John

doi:10.1016/s0040-4020(01)01028-6

Cited by 23 publications

(8 citation statements)

References 42 publications

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“…1 H NMR, 13 C, and two-dimensional NMR spectra were recorded on Varian Mercury 300, 400, 500, 600, or 700 MHz spectrometers. 11 B NMR spectra were recorded using a Bruker 400/500 MHz spectrometer at 128/160 MHz and referenced to an external standard of BF 3 •Et 2 O (δ = 0 ppm). 19 F NMR spectra were recorded using a Bruker 400 MHz spectrometer at 376 MHz and referenced to an external standard of CFCl 3 (δ = 0 ppm).…”

Section: ■ Conclusionmentioning

confidence: 99%

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De Novo Design of Boron-Based Peptidomimetics as Potent Inhibitors of Human ClpP in the Presence of Human ClpX

et al. 2019

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Boronic acids have attracted the attention of synthetic and medicinal chemists due to boron’s ability to modulate enzyme function. Recently, we demonstrated that boron-containing amphoteric building blocks facilitate the discovery of bioactive aminoboronic acids. Herein, we have augmented this capability with a de novo library design and a virtual screening platform modified for covalent ligands. This technique has allowed us to rapidly design and identify a series of α-aminoboronic acids as the first inhibitors of human ClpXP, which is responsible for the degradation of misfolded proteins.

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Section: ■ Conclusionmentioning

confidence: 99%

“…b Two signals arise in the 11 B NMR because there is some coordination from the amide oxygen to the boron center. 42,43…”

Section: ■ Associated Contentmentioning

confidence: 99%

De Novo Design of Boron-Based Peptidomimetics as Potent Inhibitors of Human ClpP in the Presence of Human ClpX

et al. 2019

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“…For example, phenylboronic acid and substituted phenylboronic acids were found to be strong competitive inhibitors of subtilisin and chymotrypsin [6]. More recently, boronic acids have been used for the synthesis of inhibitors against thrombin [50,51], lactamases [52], dipeptidyl peptidases [53], and others [54,55]. In this section, thrombin inhibitors will be used as examples.…”

Section: Protease Inhibitors That Bind To One Side Of the Active Sitementioning

confidence: 99%

Biological and Medicinal Applications of Boronic Acids

Yang¹,

Gao

Wang

2005

Boronic Acids

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“…The formation of arylboronates by such S N Ar reactions represents a complementary process to the recently disclosed S N 2 substitutions of methylphenylboronic acid derivatives by thiols and amines. 16 All reagents and solvents were purchased from Aldrich and Lancaster and were used without purification. Product 2 was used in subsequent substitution reactions without further purifications.…”

Section: Figurementioning

confidence: 99%

Synthesis ofpara-Substituted 3-Formyl Arylboronic Esters

Holland¹,

Spencer²,

Deadman³

2002

Synthesis

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S y n t h e s i s o f p a r a -S u b s t i t u t e d 3 -F o r m y l A r y l b o r o n i c E s t e r sAbstract: The synthesis of novel para-substituted amino-and phenoxy-3-formylarylboronic acids is described. These compounds are formed by the hitherto unreported nucleophilic aromatic substitution of fluorine with a range of phenols and amines in the presence of a boronic acid moiety. These reactions proceed in moderate to good yields (37-92%) and provide a useful regioselective synthetic route to trisubstituted arylboronates. These compounds are important both as intermediates in organic synthesis and as end products in their own right.

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Synthesis of ortho-modified mercapto- and piperazino-methyl-phenylboronic acid derivatives

Cited by 23 publications

References 42 publications

De Novo Design of Boron-Based Peptidomimetics as Potent Inhibitors of Human ClpP in the Presence of Human ClpX

De Novo Design of Boron-Based Peptidomimetics as Potent Inhibitors of Human ClpP in the Presence of Human ClpX

Biological and Medicinal Applications of Boronic Acids

Synthesis ofpara-Substituted 3-Formyl Arylboronic Esters

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