Development and Scale-Up of an Optimized Route to the Peptide Boronic Acid, CEP-18770

Roemmele, Renee C.; Christie, Michael

doi:10.1021/op400010u

Cited by 23 publications

(18 citation statements)

References 12 publications

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“…The importance of chiral α-amino boronic acid derivatives has been demonstrated in pharmaceutically useful protease inhibitors such as bortezomib, 1 delanzomib, 2 and ixazomib. 3 In addition, their use in transition-metal-catalyzed stereospecific C–C bond forming reactions has also gained growing attention.…”

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confidence: 99%

Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles

et al. 2018

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confidence: 99%

Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles

et al. 2018

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“…Furthermore, in the synthesis of boropeptides, such as Delanzomib, the process synthesis is not so different from the discovery synthesis. Similar methodologies allow for more efficient development [138].…”

Section: Synthesis Of Boronic Acid Drugsmentioning

confidence: 99%

“…Furthermore, boronic acids at the β-position of an electron withdrawing group were discovered to be susceptible to deprotection by forming an ionic bicyclic structure with diethanolamine, followed by acidic hydrolysis (Figure 37) [160]. Interestingly, this cage-like bicyclic intermediate was used in the process chemistry synthesis of a Delanzomib pro-drug for clinical trials, as it improved purity and stability [138]. [154][155][156][157][158][159]; (B) conversion of β boronic esters to boronic acids via diethanolamine cages [160].…”

Section: Deprotection Of Boronic Ester Pro-drugsmentioning

confidence: 99%

Design and discovery of boronic acid drugs

Plescia

Moitessier

2020

European Journal of Medicinal Chemistry

146

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Research related to boronic acids, from synthetic development to materials to drug discovery, has skyrocketed in the past 20 years. In terms of drug discovery, the incorporation of boronic acids into medicinal chemistry endeavours has seen a steady increase in recent years. In fact, the Food and Drug Administration (FDA) and Health Canada have thus far approved five boronic acid drugs, three of which were approved in the past four years, and several others are in clinical trials. Boronic acids have several desirable properties that has led to their increased use, including potentially enhancing potency of drugs and/or improving their pharmacokinetics profile. This review explores discovery processes of boronic acid drugs. It begins with a brief scope of boron in natural products and in current drugs, followed by an investigation into the various rationalizations for boronic acid incorporation and the synthetic developments that focused on facilitating their addition into organic compounds. We hope that the knowledge we have assembled in this literature review will encourage medicinal chemists to consider the potential benefits of incorporating boronic acids into their future drug discovery endeavours. Contents 1. Introduction 2. Occurrence of boron in nature. Boron in bacteria. Boron in plants. Importance in mammalian systems3. Scope of boronic acid drugs 3.1. Approved boron-containing drugs 3.2. Boron-containing drugs under investigation 3.3. Over-the-counter boron-containing drugs and supplements 3.4. Boron-containing compounds in drug discovery 3.4.1. Anti-cancer boron-containing compounds 3.4.2. Anti-viral boron-containing compounds 3.4.3. Other anti-infective boron-containing compounds 3.4.4. Other therapeutic applications of boron-containing compounds 3.

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“…Although Matteson, and others, established the synthetic utility of this process in a number of elegant natural product and pharmaceutical syntheses, its potential as a strategy for iterative homologation and the introduction of multiple stereocentres is limited by one key aspect: the reaction proceeds under substrate control . The stereochemical course of the homologation is controlled by the chirality of the diol.…”

Section: 2‐metallate Rearrangements Of Boronate Complexesmentioning

confidence: 99%

Asymmetric Synthesis of Secondary and Tertiary Boronic Esters

et al. 2017

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Non-racemic chiral boronic esters are recognised as immensely valuable building blocks in modern organic synthesis. Their stereospecific transformation into a variety of functional groups-from amines and halides to arenes and alkynes-along with their air and moisture stability, has established them as an important target for asymmetric synthesis. Efforts towards the stereoselective synthesis of secondary and tertiary alkyl boronic esters have spanned over five decades and are underpinned by a wealth of reactivity platforms, drawing on the unique and varied reactivity of boron. This Review summarizes strategies for the asymmetric synthesis of alkyl boronic esters, from the seminal hydroboration methods of H. C. Brown to the current state of the art.

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Development and Scale-Up of an Optimized Route to the Peptide Boronic Acid, CEP-18770

Cited by 23 publications

References 12 publications

Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles

Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles

Design and discovery of boronic acid drugs

Asymmetric Synthesis of Secondary and Tertiary Boronic Esters

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