Efficient synthesis and in vitro cytostatic activity of 4-substituted triazolyl-nucleosides

Akri, Khalid El; Bougrin, Khalid; Balzarini, Jan; Faraj, Abdesslem; Benhida, Rachid

doi:10.1016/j.bmcl.2007.08.077

Cited by 98 publications

(46 citation statements)

References 15 publications

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“…The efficiency of Cu 2 O-NPs has also been evaluated in the cyclisation of a variety of ring systems. [41] In the above article the cycloaddition of a terminal alkyne and an azide was carried out under MW conditions with Cu I as catalyst and under solvent-free conditions, leading to the desired product in a quantitative yield and with a reaction time of one minute. [38] Moreover, the Cu 2 O-NPs catalyst demonstrates less cytotoxicity and higher efficiency than traditional Cu I -generating systems.…”

Section: 4-disubstituted 123-triazolesmentioning

confidence: 99%

1,2,3‐Triazole in Heterocyclic Compounds, Endowed with Biological Activity, through 1,3‐Dipolar Cycloadditions

et al. 2014

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1,3-Dipolar cycloaddition reactions can be considered a powerful synthetic tool in the building of heterocyclic rings, with applications in different fields. In this review we focus on the synthesis of biologically active compounds possessing the 1,2,3-triazole core through 1,3-dipolar cycloaddition reactions. The 1,2,3-triazole skeleton can be present as a single disubstituted ring, as a linker between two molecules, or embedded in a polyheterocycle. The cycloaddition reactions are usually catalysed by copper or ruthenium. Domino reactions can be achieved through dipolarophile anion formation, generally followed by cyclisation. The variety of attainable heterocyclic structures gives an illustration of the importance of the 1,2,3-triazole core in medicinal chemistry

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Section: 4-disubstituted 123-triazolesmentioning

confidence: 99%

1,2,3‐Triazole in Heterocyclic Compounds, Endowed with Biological Activity, through 1,3‐Dipolar Cycloadditions

et al. 2014

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“…Whilst both imidazole and triazole are five membered ring heterocycles, imidazole contains two ring nitrogen atoms, whereas triazoles have three. However, compared with imidazoles (clotrimazole, ketoconazole, miconazole), triazoles are less susceptible to metabolic degradation and have much greater target specificity, increased potency and an expanded spectrum of activity [25–26]. …”

Section: Introductionmentioning

confidence: 99%

Advances in synthetic approach to and antifungal activity of triazoles

Shalini¹,

Kumar²,

Drabu³

et al. 2011

Beilstein J. Org. Chem.

149

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SummarySeveral five membered ring systems, e.g., triazole, oxadiazole dithiazole and thiadiazole with three heteroatoms at symmetrical or asymmetrical positions have been studied because of their interesting pharmacological properties. In this article our emphasis is on synthetic development and pharmacological activity of the triazole moiety which exhibit a broad spectrum of pharmacological activity such as antifungal, antibacterial, anti-inflammatory and anticancer etc. Triazoles have increased our ability to treat many fungal infections, for example, candidiasis, cryptococcal meningitis, aspergillosis etc. However, mortality due to these infections even with antifungal therapy is still unacceptably high. Therefore, the development of new antifungal agents targeting specific fungal structures or functions is being actively pursued. Rapid developments in molecular mycology have led to a concentrated search for more target antifungals. Although we are entering a new era of antifungal therapy in which we will continue to be challenged by systemic fungal diseases, the options for treatment will have greatly expanded.

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“…In this case [Cp*RuCl] 4 was a better catalyst than [Cp*RuCl(PPh 3 ) 2 ] [59]. Similar 4-substituted triazolyl-nucleosides have been obtained from suitably protected azido ribose [60] or deoxyribose [61] and different acetylene derivatives, by solvent-free MW-promoted CuAAC (Scheme 21), or in CH 2 Cl 2 solution by conventional heating in the presence of acetic acid. In the first case, all the reactants have been dispersed on SiO 2 and then irradiated with MW at 110°C for 1 min obtaining the desired products in 95% yields.…”

Section: Nucleoside and Nucleotide Triazole Derivatives And Analoguesmentioning

confidence: 98%

Click Chemistry Under Microwave or Ultrasound Irradiation

Tagliapietra¹,

Binello²,

Cravotto

2011

COC

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The copper-catalyzed azide-alkyne cycloaddition (CuAAC) is generally recognized as the most striking example of "click reaction". CuAAC fit so well into Sharpless' definition that it became almost synonymous with "click chemistry" itself. The most common catalyst systems employ Cu(II) salt in the presence of a reducing agent (i.e. sodium ascorbate) to generate the required Cu(I) catalyst in situ or as an alternative the comproportionation of Cu(II)/Cu(0) species. Although, Cu(I) catalyzes the reaction with a rate enhancement of 10 7 even in the absence of ligands and provides a clean and selective conversion to the 1,4-substituted triazoles, some bulky and scantily reactive substrates still require long reaction times and often few side products are formed. Outstanding results have been achieved by performing CuAAC under microwave (MW) irradiation. Several authors described excellent yields, high purity and short reaction times. In few cases also power ultrasound (US) accelerated the reaction, especially when heterogeneous catalysts or metallic copper are employed. The aim of this review is to summarize and highlight the huge advantages offered by MW-and US-promoted CuAAC. In the growing scenario of innovative synthetic strategies, we intend to emphasize the complementary role played by these non-conventional energy sources and click chemistry to achieve process intensification in organic synthesis.

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Efficient synthesis and in vitro cytostatic activity of 4-substituted triazolyl-nucleosides

Cited by 98 publications

References 15 publications

1,2,3‐Triazole in Heterocyclic Compounds, Endowed with Biological Activity, through 1,3‐Dipolar Cycloadditions

1,2,3‐Triazole in Heterocyclic Compounds, Endowed with Biological Activity, through 1,3‐Dipolar Cycloadditions

Advances in synthetic approach to and antifungal activity of triazoles

Click Chemistry Under Microwave or Ultrasound Irradiation

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