Reactions under the Click Chemistry Philosophy Employed in Supramolecular and Mechanostereochemical Systems

Fahrenbach, Albert C.; Stoddart, J. Fraser

doi:10.1002/asia.201100457

Cited by 70 publications

(38 citation statements)

References 83 publications

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“…Organic azides in general are popular in recent times because of their use as synthons in Cu(I)-catalyzed “click chemistry” [19]. It is also well known that organic molecules having terminal ethynyl functional groups are very useful synthons for the design of interesting materials in polymer and supramolecular chemistry [20–25]. …”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and DNA interaction studies of new triptycene derivatives

Chakraborty¹,

Mondal²,

Kumari³

et al. 2014

Beilstein J. Org. Chem.

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SummaryA facile and efficient synthesis of a new series of triptycene-based tripods is being reported. Using 2,6,14- or 2,7,14-triaminotriptycenes as synthons, the corresponding triazidotriptycenes were prepared in high yield. Additionally, we report the transformation of 2,6,14- or 2,7,14-triaminotriptycenes to the corresponding ethynyl-substituted triptycenes via their tribromo derivatives. Subsequently, derivatization of ethynyl-substituted triptycenes was studied to yield the respective propiolic acid and ethynylphosphine derivatives. Characterization of the newly functionalized triptycene derivatives and their regioisomers were carried out using FTIR and multinuclear NMR spectroscopy, mass spectrometry, and elemental analyses techniques. The study of the interaction of these trisubstituted triptycenes with various forms of DNA revealed interesting dependency on the functional groups of the triptycene core to initiate damage or conformational changes in DNA.

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Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and DNA interaction studies of new triptycene derivatives

Chakraborty¹,

Mondal²,

Kumari³

et al. 2014

Beilstein J. Org. Chem.

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“…In particular, the multiple multicomponent macrocyclizations including bifunctional building blocks (MiB) technique has been used for a number of potentially interesting structures (Figure 11.22). 376 (281), b-lactam-containing macrocycles, steroid-peptoid macrocycles (282), macroheterocycles (283) and large macrobicycles. However, specific applications for these libraries in pharmaceutical discovery have not been reported.…”

Section: Synthesis At Scalementioning

confidence: 99%

“…281 Applications relevant to drug discovery to date have been limited to these two examples, although the transformation has seen greater utility for molecular architecture investigations. 282 Another [3+2]-cycloaddition process that has proven value in the construction of macrocyclic natural products, but has been underexplored to date for medicinal chemistry purposes, is the intramolecular addition of nitrile oxides (typically generated in situ from the corresponding oxime) with alkenes (Scheme 11.23). For example, this reaction has been employed for the conversion of oxime-acrylate 172 into 173, an intermediate for the synthesis of the macrosphelide skeleton, 283 and for the construction of macrocycles useful in studies directed towards an asymmetric synthesis of brefeldin A.…”

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confidence: 99%

The Synthesis of Macrocycles for Drug Discovery

Peterson¹

2014

Macrocycles in Drug Discovery

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Despite the attractive nature of macrocyclic compounds for use in new pharmaceutical discovery, applications have been hindered due to the lack of appropriate synthetic methods, in particular for the construction of libraries of such molecules. However, over the last decade, a number of effective and versatile methodologies suitable for macrocyclic scaffolds have been developed and applied successfully. These include classical coupling and substitution reactions, ring-closing metathesis (RCM), cycloaddition (“click”) chemistry, multicomponent reactions (MCR), numerous organometallic-mediated processes and others. This chapter presents a comprehensive compilation of these strategies and provides examples of their use in drug discovery, along with a description of those approaches that have proven effective for the assembly of macrocyclic libraries suitable for screening.

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“…However, the scope of triazole chemistry is not confined to drug discovery. There are an increasing number of applications in numerous other areas of modern chemical sciences, such as bioconjugation [13], supramolecular chemistry, [14] and polymer sciences [15]. …”

Section: Introductionmentioning

confidence: 99%

Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale production

Ötvös¹,

Georgiádes²,

Mándity³

et al. 2013

Beilstein J. Org. Chem.

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SummaryThe preparation of novel multi-substituted 1,2,3-triazole-modified β-aminocyclohexanecarboxylic acid derivatives in a simple and efficient continuous-flow procedure is reported. The 1,3-dipolar cycloaddition reactions were performed with copper powder as a readily accessible Cu(I) source. Initially, high reaction rates were achieved under high-pressure/high-temperature conditions. Subsequently, the reaction temperature was lowered to room temperature by the joint use of both basic and acidic additives to improve the safety of the synthesis, as azides were to be handled as unstable reactants. Scale-up experiments were also performed, which led to the achievement of gram-scale production in a safe and straightforward way. The obtained 1,2,3-triazole-substituted β-aminocyclohexanecarboxylates can be regarded as interesting precursors for drugs with possible biological effects.

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Reactions under the Click Chemistry Philosophy Employed in Supramolecular and Mechanostereochemical Systems

Cited by 70 publications

References 83 publications

Synthesis, characterization and DNA interaction studies of new triptycene derivatives

Synthesis, characterization and DNA interaction studies of new triptycene derivatives

The Synthesis of Macrocycles for Drug Discovery

Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale production

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