Economical and scalable synthesis of 6-amino-2-cyanobenzothiazole

Hauser, Jacob R.; Beard, H. M.; Bayana, ME; Jolley, Katherine E.; Warriner, S. L.; Bon, Robin S.

doi:10.3762/bjoc.12.189

Cited by 16 publications

(18 citation statements)

References 18 publications

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“…16 Palladium-catalyzed amination using xantphos as ligand 17,18 allowed synthesis of the morpholine analogue in 71% yield vs 12% for the S N Ar reaction (Scheme 2). Additionally, the thiomorpholine dioxide analogue was obtained in 74% yield, and the azetidine in 33% yield (low, but vastly improved over 2%).…”

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confidence: 99%

Rapid Access to a Broad Range of 6′-Substituted Firefly Luciferin Analogues Reveals Surprising Emitters and Inhibitors

et al. 2017

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Light-emitting firefly luciferin analogues contain electron-donating groups in the 6′-position, but the scope of known 6′-substitution remains narrow. A two-step route to a broad range of 6′-substituted luciferin analogues was developed to fill this void and enable more extensive study of the 6′-functionality. This chemistry allowed direct access to “caged” amide and bright azetidine analogues, but also revealed thioether inhibitors and unexpectedly luminogenic aryl amine derivatives.

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confidence: 99%

Rapid Access to a Broad Range of 6′-Substituted Firefly Luciferin Analogues Reveals Surprising Emitters and Inhibitors

et al. 2017

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“…Luciferin analogues are made with the same procedure by starting from a substituted cyanobenzothiazole. The synthesis of intermediate 46 was improved over the years and several procedures are available [ 57 , 58 , 59 ], the most popular involving the dehydration of a benzothiazole amide, a Sandmeyer reaction using a cyanide source or a Michael condensation with benzoquinone [ 59 ]. An interesting synthetic route towards cyanobenzothiazole 46 was reported by Prescher et al ( Scheme 8 B), starting from the condensation of p-methoxyaniline 48 43 with Appel’s salt 44, to generate thioformamide 45.…”

Section: Classification Of Synthetic Enzyme Substratesmentioning

confidence: 99%

Modified Enzyme Substrates for the Detection of Bacteria: A Review

Pala¹,

Širec²,

Spitz³

2020

Molecules

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The ability to detect, identify and quantify bacteria is crucial in clinical diagnostics, environmental testing, food security settings and in microbiology research. Recently, the threat of multidrug-resistant bacterial pathogens pushed the global scientific community to develop fast, reliable, specific and affordable methods to detect bacterial species. The use of synthetically modified enzyme substrates is a convenient approach to detect bacteria in a specific, economic and rapid manner. The method is based on the use of specific enzyme substrates for a given bacterial marker enzyme, conjugated to a signalogenic moiety. Following enzymatic reaction, the signalophor is released from the synthetic substrate, generating a specific and measurable signal. Several types of signalophors have been described and are defined by the type of signal they generate, such as chromogenic, fluorogenic, luminogenic, electrogenic and redox. Signalophors are further subdivided into groups based on their solubility in water, which is key in defining their application on solid or liquid media for bacterial culturing. This comprehensive review describes synthetic enzyme substrates and their applications for bacterial detection, showing their mechanism of action and their synthetic routes.

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“…7 Many of these scaffolds also comprise key functional handles for latestage diversification (Figure 2). Efforts to expediently synthesize amino luciferins 8 and related analogues 9 are similarly facilitating more widespread use of bioluminescent tools.…”

Section: ■ Bioluminescence Basicsmentioning

confidence: 99%

Bioluminescent Probes for Imaging Biology beyond the Culture Dish

Rathbun

Prescher

2017

Biochemistry

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Bioluminescence with luciferase-luciferin pairs is an attractive method for surveying cells in live tissues and whole organisms. Recent advances in luciferin chemistry and luciferase engineering are further expanding the scope of the technology. It is now possible to spy on cells in a variety of deep tissues and visualize multicellular interactions—feats that are enabling new questions to be asked and new ideas to be explored. This perspective piece highlights recent successes in bioluminescent probe development and their applications to imaging in live cells, tissues, and animals.

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Economical and scalable synthesis of 6-amino-2-cyanobenzothiazole

Cited by 16 publications

References 18 publications

Rapid Access to a Broad Range of 6′-Substituted Firefly Luciferin Analogues Reveals Surprising Emitters and Inhibitors

Rapid Access to a Broad Range of 6′-Substituted Firefly Luciferin Analogues Reveals Surprising Emitters and Inhibitors

Modified Enzyme Substrates for the Detection of Bacteria: A Review

Bioluminescent Probes for Imaging Biology beyond the Culture Dish

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