A new bicyclic oxazaborines with a bridged nitrogen atom, their thermic rearrangement and fluorescence properties

Josefík, František; Svobodová, Markéta; Bertolasi, Valerio; Šimůnek, Petr; Macháček, Vladimı́r; Almonasy, Numan; Černošková, E.

doi:10.1016/j.jorganchem.2011.11.004

Cited by 25 publications

(15 citation statements)

References 24 publications

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“…The R factors obtained for NBC6 and NBC11 were 4.08% and 2.83%, respectively. The B atom lies out of the ring plane in a boat-envelope conformation in both oxazaborine structures, whereas the other atoms in the heterocycle are planar and are involved in a π-electron conjugated system ( Figure 4 A) as previously reported for other oxazaborines ( Josefíka et al., 2012 , Mikyseka et al., 2017 ). NBC6 is chelated to B through O/N chelation of the amide C=O and enamine NH ( Figure 4 A), whereas NBC11 is chelated to B through O/N chelation of the ketone C=O and enamine NH ( Figure 4 B).…”

Section: Resultssupporting

confidence: 63%

Boron-Based Inhibitors of the NLRP3 Inflammasome

Baldwin

Rivers-Auty

Daniels

et al. 2017

Cell Chemical Biology

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SummaryNLRP3 is a receptor important for host responses to infection, yet is also known to contribute to devastating diseases such as Alzheimer's disease, diabetes, atherosclerosis, and others, making inhibitors for NLRP3 sought after. One of the inhibitors currently in use is 2-aminoethoxy diphenylborinate (2APB). Unfortunately, in addition to inhibiting NLRP3, 2APB also displays non-selective effects on cellular Ca2+ homeostasis. Here, we use 2APB as a chemical scaffold to build a series of inhibitors, the NBC series, which inhibit the NLRP3 inflammasome in vitro and in vivo without affecting Ca2+ homeostasis. The core chemical insight of this work is that the oxazaborine ring is a critical feature of the NBC series, and the main biological insight the use of NBC inhibitors led to was that NLRP3 inflammasome activation was independent of Ca2+. The NBC compounds represent useful tools to dissect NLRP3 function, and may lead to oxazaborine ring-containing therapeutics.

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Section: Resultssupporting

confidence: 63%

Boron-Based Inhibitors of the NLRP3 Inflammasome

Baldwin

Rivers-Auty

Daniels

et al. 2017

Cell Chemical Biology

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“…Enaminones 3 were prepared as previously reported [12] (Scheme 3). The last step of the synthesis is the deacetylation of 7 by sodium in ethanol.…”

Section: Resultsmentioning

confidence: 99%

A simple, enaminone-based approach to some bicyclic pyridazinium tetrafluoroborates

Josefík¹,

Svobodová²,

Bertolasi³

et al. 2013

Beilstein J. Org. Chem.

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SummaryEasily obtainable cyclic enaminones (piperidin-2-ylidenealkanones) can be transformed into substituted bicyclic pyridazinium tetrafluoroborates upon treatment with corresponding diazonium salts. The transformation can be performed either in a one-pot way or in a two-step process with the isolation of single azo-coupled enaminone as the intermediate. The former method is superior. Under the optimized conditions, a number of pyridazinium salts substituted with both electron-donating and electron-withdrawing substituents was easily synthesized. A mechanism of the formation of the pyridazinium salts is suggested. A partial drawback is the possibility of the formation of a mixture of products when using a different diazonium salt in each step due to a reversibility of the azo coupling. This can be suppressed by using a more reactive diazonium salt before a less reactive one.

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“…Exocyclic vinylogous amides built on a piperidine ring are versatile intermediates in the preparation of many N ‐heterocycles and natural alkaloids (Fig. ), such as desoxoprosophylline, cassine, pinidinone, deoxyfebrifugine and norallosedamine, among others .…”

Section: Alkaloids From Vinylogous Amidesmentioning

confidence: 99%

From synthetic control to natural products: a focus on N‐heterocycles

Prandi

Occhiato

2019

Pest Management Science

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Natural products containing a N‐heterocycle motif are widespread in nature and medicinal plants, in particular, have proved to be a source of almost unlimited N‐derived structures with high molecular diversity. Because of their intrinsic potential for use in both biomedical and agricultural applications, there is a general need for new compounds and for the synthesis of ‘natural‐inspired’ analogues. Importantly, transition of a natural product from discovery to a ‘market lead’ is associated with an increasingly challenging demand for more of the compound, which cannot be met by isolation from natural plant sources, often due to low extraction yields and uneven availability of the plant source itself. Synthesis remains the most reliable approach to provide valuable products for the market. In this review, a comprehensive overview of our contribution to synthetic access to N‐derived natural products is given. Major strengths of the proposed methodologies are discussed critically. © 2019 Society of Chemical Industry

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A new bicyclic oxazaborines with a bridged nitrogen atom, their thermic rearrangement and fluorescence properties

Cited by 25 publications

References 24 publications

Boron-Based Inhibitors of the NLRP3 Inflammasome

Boron-Based Inhibitors of the NLRP3 Inflammasome

A simple, enaminone-based approach to some bicyclic pyridazinium tetrafluoroborates

From synthetic control to natural products: a focus on N‐heterocycles

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