Terminal alkyne-functionalized triazine by Sonogashira coupling: synthesis of a potential cell signalling inhibitor via click chemistry

Courme, Caroline; Gillon, Sophie; Gresh, Nohad; Vidal, Michel; Garbay, Christiane; Florent, Jean‐Claude

doi:10.1016/j.tetlet.2008.05.050

Cited by 23 publications

(10 citation statements)

References 25 publications

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“…48 4-Azidophenol was successfully esterified under these conditions with yields in the range from 77% to almost quantitative. All characterisation data for the new aromatic azide precursors are available in the ESI †.…”

Section: Resultsmentioning

confidence: 99%

Functional star-shaped tris(triazolyl)triazines: columnar liquid crystal, fluorescent, solvatofluorochromic and electrochemical properties

et al. 2012

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Columnar liquid crystals with a C 3 star-shaped heteroaromatic nitrogen-rich core, i.e. 2,4,6-tris(1 0 ,2 0 ,3 0 -triazol-4 0 -yl)-1,3,5-triazine (TTT), that show luminescence and solvatofluorochromism, and are also electron-acceptors are described. The core has been extended with polyalkoxybenzoyloxyphenyl groups situated at the 1 position of the 1,2,3-triazole rings to obtain molecules with three, six or nine ndecyloxy chains (series TB) or three, six or nine (S)-3,7-dimethyloctyloxy chains (series TB*). The preparation of the target compounds involved a copper-catalysed alkyne-azide cycloaddition (CuAAC) ''click chemistry'' procedure with a 1,3,5-triazine precursor and aromatic azides and this proved to be a versatile way to functionalise the periphery of the heteroaromatic core. Comparison of these compounds and those bearing polyalkoxyphenyl substituents (series T) has led to a deeper understanding of the self-assembly of the compounds with the TTT core. It was found that they selforganise into columnar mesophases, in which two molecules with a low-symmetry conformation occupy on average a columnar stratum. These molecules tend to adopt a polar conformation instead of the apolar C 3 conformation and arrange in an antiparallel assembly. For some compounds the molecules in this arrangement have enough flexibility to tilt upon lowering temperature or by applying an electric field. Interestingly, the hexagonal columnar arrangement is preserved in a glassy state at room temperature. Furthermore, the mesophases show luminescence in the blue region of the visible spectrum depending on the peripheral substitution and molecular structure. We also report a novel property of TTT compounds (series T, TB and TB*) as they are able to act as solvatofluorochromic probes, a property that allowed us to estimate the overall polarity of the liquid crystalline medium. An aromatic azide precursor was also found to be mesomorphic and exhibited a monolayer SmA mesophase.

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Section: Resultsmentioning

confidence: 99%

Functional star-shaped tris(triazolyl)triazines: columnar liquid crystal, fluorescent, solvatofluorochromic and electrochemical properties

et al. 2012

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“…Initially, the key precursors ( 311 ) were derived in two steps from para ‐aminophenol ( 309 ). The diazotization of para ‐aminophenol ( 309 ) by using NaNO 2 /HCl, followed by treatment with sodium azide, delivered para ‐hydroxyphenylazide ( 310 ) . Then, treatment with a variety of polyalkoxybenzoic acids in the presence of N , N′ ‐dicyclohexylcarbodiimide (DCC) and 4‐dimethylaminopyridine (DMAP) led to the formation of the corresponding azides ( 311 ).…”

Section: Carbon−nitrogen Bond‐forming Reactionsmentioning

confidence: 99%

Synthetic Approaches to Star‐Shaped Molecules with 1,3,5‐Trisubstituted Aromatic Cores

Kotha

Meshram

Panguluri

et al. 2019

Chemistry An Asian Journal

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Herein, we summarize the synthetic approaches that have been developed for the synthesis of star‐shaped molecules. Typically, to design such highly functionalized molecules, simple building blocks are first assembled through trimerization reactions, starting from commercially available starting materials. Then, these building blocks are synthetically manipulated to generate extended star‐shaped molecules. We also discuss the syntheses of star‐shaped molecules that contain 2,4,6‐trisubstituted 1,3,5‐triazine or 1,3,5‐trisubstituted benzene rings as a central core and diverse substituted styrene, phenyl, and fluorene derivatives at their periphery, which endows these molecules with extended conjugation. A variety of metal‐catalyzed reactions, such as Suzuki, Buchwald–Hartwig, Sonogashira, Heck, and Negishi cross‐coupling reactions, as well as metathesis, have been employed to functionalize a range of star‐shaped molecules. The methods described herein will be helpful for designing a wide range of intricate compounds that are highly valuable in the fields of supramolecular chemistry and materials science. Owing to space limitations, we will not cover all of the publications on this topic. Instead, we will focus on examples that were reported by our research group and other relevant recent literature. Apart from the trimerization sequence, this Minireview has been structured based on the key reactions that were used to prepare the star‐shaped molecules and other higher analogues. Finally, some examples that do not fit into this classification are discussed.

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“…1). The method utilized for the synthesis of these acetylenic compounds is the palladium catalyzed cross-coupling between alk-1-ynes and 2-chloro-4,6-dimethoxy-1,3,5-triazine [36][37][38]. As for their 2-alkyl analogs, they were often obtained by reacting zinc bis(imino-bismethyl carbamate) 3 with acid chloride or anhydride [25,26,33,34], and we have reported that 4 Å molecular sieves and pyridine can be advantageously utilized in this reaction [39,40].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of a new class of triazin–triazoles as potential inhibitors of human farnesyltransferase

et al. 2015

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A new synthesis of ethynyldimethoxytriazine 1, an important platformcompound for developing new chemical entities for anticancer research and for other biological applications, is described. Compound 1 was further reacted with azides 5a-i to provide triazin-triazoles 2a-i, which were tested on human farnesyltransferase and on the NCI-60 human tumor cell lines. Synthesis of other dimethoxytriazine derivatives 15 and 16, linked to a sp 2 or a sp 3 carbon atom were also studied. Electronic supplementary material The online version of this article (2a-i target compounds CO 2 H 2c: IC 50 (human FTase) = 38.6 µM

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Terminal alkyne-functionalized triazine by Sonogashira coupling: synthesis of a potential cell signalling inhibitor via click chemistry

Cited by 23 publications

References 25 publications

Functional star-shaped tris(triazolyl)triazines: columnar liquid crystal, fluorescent, solvatofluorochromic and electrochemical properties

Functional star-shaped tris(triazolyl)triazines: columnar liquid crystal, fluorescent, solvatofluorochromic and electrochemical properties

Synthetic Approaches to Star‐Shaped Molecules with 1,3,5‐Trisubstituted Aromatic Cores

Synthesis and biological evaluation of a new class of triazin–triazoles as potential inhibitors of human farnesyltransferase

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