115666-46-1Relevant academic research and scientific papers
Diastereoselective Total Synthesis of Raputindole A
Kock, Mario,Lindel, Thomas
, p. 5444 - 5447 (2018)
The first diastereoselective total synthesis of the bisindole alkaloid raputindole A is reported. After Au(I)-catalyzed assembly of the cyclopenta[f]indole tricycle, it was possible to hydrogenate the indene double bond regio- A nd diastereoselectively through iridium catalysis, guided by a preinstalled hydroxy function. Attempted HWE reaction led to formal elimination of formaldehyde from an α-quaternary cyclopentane carbaldehyde, which was circumvented by Takai olefination. After Suzuki-Miyaura cross coupling and deprotection/oxidation, (±)-raputindole A was obtained in 13 linear steps in 18% overall yield.
A Bifunctional Fluorogenic Rhodamine Probe for Proximity-Induced Bioorthogonal Chemistry
Werther, Philipp,M?hler, Jasper S.,Wombacher, Richard
, p. 18216 - 18224 (2017)
Bioorthogonal reactions have emerged as a versatile tool in life sciences. The inverse electron demand Diels–Alder reaction (DAinv) stands out due to the availability of reactants with very fast kinetics. However, highly reactive dienophiles suffer the disadvantage of being less stable and prone to side reactions. Herein, we evaluate the extent of acceleration of rather unreactive but highly stable dienophiles by DNA-templated proximity. To this end, we developed a modular synthetic route for a novel bifunctional fluorogenic tetrazine rhodamine probe that we used to determine the reaction kinetics of various dienophiles in a fluorescence assay. Under proximity-driven conditions the reaction was found to be several orders of magnitude faster, and we observed almost no background reaction when proximity was not induced. This fundamental study identifies a minimally sized fluorogenic tetrazine dienophile reactant pair that has potential to be generally used for the visualization of biomolecular interactions with temporal and spatial resolution in living systems.
Total Synthesis and Absolute Configuration of Raputindole A
Kock, Mario,Jones, Peter G.,Lindel, Thomas
, p. 6296 - 6299 (2017)
The first total synthesis of the bisindole alkaloid raputindole A from the rutaceous plant Raputia simulans is reported. The key step is a Au(I)-catalyzed cyclization that assembles the cyclopenta[f]indole tricycle from a 6-alkynylated indoline precursor. The isobutenyl side chain was installed by Suzuki-Miyaura cross-coupling, followed by a regioselective reduction employing LiDBB. Starting from 6-iodoindole, the sequence needs nine steps and provided (±)-raputindole A in 6.6% overall yield. The absolute configuration of the natural product (+)-raputindole A was determined by quantum chemical calculation of the ECD spectrum.
Synthesis of photoactivatable azido-acyl caged oxazine fluorophores for live-cell imaging
Anzalone, Andrew V.,Chen, Zhixing,Cornish, Virginia W.
, p. 9442 - 9445 (2016)
We report the design and synthesis of a photoactivatable azido-acyl oxazine fluorophore. Photoactivation is achieved cleanly and rapidly with UV light, producing a single fluorescent oxazine photoproduct. We demonstrate the utility of azido-acyl caged oxazines for protein specific labeling in living mammalian cells using the TMP-tag technology.
Synthesis of Pyranocyclopentaindolines Representing the Western Sections of Janthitrem B, JBIR-137, and Shearinine G
Fresia, Marvin,Lindel, Thomas
, (2022/02/05)
The synthesis of the ABCD tetracyclic partial structures of the fungal indole diterpenes janthitrem B, JBIR-137, and shearinine G is reported. The route starts from 5-formylated indoline that is coupled to a dihydropyran moiety, followed by Prins cyclization. A diene was obtained that was oxygenated in a divergent manner. The hydroxylated tetracyclic western half of janthitrem B was obtained in eight steps and 10 % overall yield. We also share our experience with alternative approaches passing via alkynylated precursors. This includes the gold-catalyzed cycloisomerization of a 6-ethynyl-5-prenylindoline.
NEAR-INFRARED NERVE-SPARING FLUOROPHORES
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, (2020/02/17)
Provided are far red to near-infrared nerve-sparing fluorescent compounds, compositions comprising them, and methods of their use in medical procedures.
NERVE-SPECIFIC FLUOROPHORE FORMULATIONS FOR DIRECT AND SYSTEMIC ADMINISTRATION
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, (2020/03/02)
Nerve-specific fluorophore formulations for direct or systemic administration are described. The formulations can be used in fluorescence-guided surgery (FGS) to aid in nerve preservation during surgical interventions.
NEAR-INFRARED NERVE-SPARING BENZO[C]PHENOXAZINE FLUOROPHORES
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Page/Page column 50, (2020/05/07)
Provided are near-infrared nerve-sparing fluorescent compounds, compositions comprising them, and methods of their use in medical procedures.
SUBSTITUTED PYRIMIDINYL AND PYRIDINYL-PYRROLOPYRIDINONES, PROCESS FOR THEIR PREPARATION AND THEIR USE AS KINASE INHIBITORS
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, (2014/05/24)
The present invention relates to substituted pyrimidinyl- and pyridinylpyrrolopyridinone compounds which modulate the activity of protein kinases and are therefore useful in treating diseases caused by dysregulated protein kinase activity, in particular RET family kinases. The present invention also provides methods for preparing these compounds, pharmaceutical compositions comprising these compounds, and methods of treating diseases utilizing pharmaceutical compositions containing these compounds.
A common diaryl ether intermediate for the gram-scale synthesis of oxazine and xanthene fluorophores
Anzalone, Andrew V.,Wang, Tracy Y.,Chen, Zhixing,Cornish, Virginia W.
, p. 650 - 654 (2013/02/23)
Common ground: Copper-catalyzed coupling reactions can be used for the high-yielding preparation of widely used oxazine and xanthene fluorophores from a common diaryl ether intermediate on a gram-scale (see scheme). This general approach may facilitate th
