ChemInform Abstract: SYNTHESIS AND REACTIONS OF 4,5‐DICHLORO‐1,2,3‐DITHIAZOLIUM CHLORIDE

Appel, Rolf; Janssen, Heinrich; Siray, Mustafa; Knoch, Falk

doi:10.1002/chin.198532178

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(2 citation statements)

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“…For the preparation of the 1,2,3-dithiazoles, primary aromatic or heteroaromatic amines or alcohols were reacted with 4,5-dichloro-1,2,3-dithiazolium chloride (Appel's salt) I, followed by treatment with base (2 equiv) to give the corresponding [(4-chloro-5H-1,2,3-dithiazol-5-ylidene)amino]arenes or 2-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)arene-1(2H)-ones 1-53 in moderate to excellent yields [16][17][18] according to the following general procedure: to a stirred suspension of Appel's salt I (100 mg, 0.48 mmol) in dichloromethane (4 mL) at ca. 20 °C was added the corresponding aminoarene or hydroxyarene (0.48 mmol).…”

Section: Synthesis Of 123-dithiazoles 1-55mentioning

confidence: 99%

Potent inhibitors of human LAT1 (SLC7A5) transporter based on dithiazole and dithiazine compounds for development of anticancer drugs

Napolitano

Scalise

Koyioni

et al. 2017

Biochemical Pharmacology

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Section: Synthesis Of 123-dithiazoles 1-55mentioning

confidence: 99%

Potent inhibitors of human LAT1 (SLC7A5) transporter based on dithiazole and dithiazine compounds for development of anticancer drugs

Napolitano

Scalise

Koyioni

et al. 2017

Biochemical Pharmacology

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“…The route features a dithiazolium chloride reagent, known as Appel's salt (Figure 3B). 30 This material has been used to produce a wide variety of substituted heterocycles, including quinazolines and benzothiazoles, from aromatic amines. 31−34 We reasoned that Appel's salt could similarly provide rapid access to cyanobenzothiazoles, key precursors en route to luciferin scaffolds.…”

Section: ■ Designing and Synthesizing Luciferin "Batteries"mentioning

confidence: 99%

Building Biological Flashlights: Orthogonal Luciferases and Luciferins for in Vivo Imaging

Williams

Prescher

2019

Acc. Chem. Res.

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Conspectus Bioluminescence is widely used for real-time imaging in living organisms. This technology features a light-emitting reaction between enzymes (luciferases) and small molecule substrates (luciferins). Photons produced from luciferase–luciferin reactions can penetrate through heterogeneous tissue, enabling readouts of physiological processes. Dozens of bioluminescent probes are now available and many are routinely used to monitor cell proliferation, migration, and gene expression patterns in vivo. Despite the ubiquity of bioluminescence, traditional applications have been largely limited to imaging one biological feature at a time. Only a handful of luciferase–luciferin pairs can be easily used in tandem, and most are poorly resolved in living animals. Efforts to develop spectrally distinct reporters have been successful, but multispectral imaging in large organisms remains a formidable challenge due to interference from surrounding tissue. Consequently, a lack of well-resolved probes has precluded multicomponent tracking. An expanded collection of bioluminescent probes would provide insight into processes where multiple cell types drive physiological tasks, including immune function and organ development. We aimed to expand the bioluminescent toolkit by developing substrate-resolved imaging agents. The goal was to generate multiple orthogonal (i.e., noncross-reactive) luciferases that are responsive to unique scaffolds and could be used concurrently in living animals. We adopted a parallel engineering approach to genetically modify luciferases to accept chemically modified luciferins. When the mutants and analogs are combined, light is produced only when complementary enzyme–substrate partners interact. Thus, the pairs can be distinguished based on substrate selectivity, regardless of the color of light emitted. Sequential administration of the luciferins enables the unique luciferases to be illuminated (and thus resolved) within complex environments, including whole organisms. This Account describes our efforts to develop orthogonal bioluminescent probes, crafting custom luciferases (or “biological flashlights”) that can selectively process luciferin analogs (or “batteries”) to produce light. In the first section, we describe synthetic methods that were key to accessing diverse luciferin architectures. The second section focuses on identifying complementary luciferase enzymes via a combination of mutagenesis and screening. To expedite the search for orthogonal enzymes and substrates, we developed a computational algorithm to sift through large data sets. The third section features examples of the parallel engineering approach. We identified orthogonal enzyme–substrate pairs comprising two different classes of luciferins. The probes were vetted both in cells and whole organisms. This expanded collection of imaging agents is applicable to studies of immune function and other multicomponent processes. The final section of the Account highlights ongoing work toward building better bioluminescent tools. As e...

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ChemInform Abstract: SYNTHESIS AND REACTIONS OF 4,5‐DICHLORO‐1,2,3‐DITHIAZOLIUM CHLORIDE

Abstract: Die Titelverbindung (III) ist durch Umsetzung von Chloracetonitril (I) mit (II) darstellbar [oder, mit schlechterer Ausb., aus Acetonitril und (II)].

Cited by 1 publication

References 1 publication

Potent inhibitors of human LAT1 (SLC7A5) transporter based on dithiazole and dithiazine compounds for development of anticancer drugs

Potent inhibitors of human LAT1 (SLC7A5) transporter based on dithiazole and dithiazine compounds for development of anticancer drugs

Building Biological Flashlights: Orthogonal Luciferases and Luciferins for in Vivo Imaging

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