scholarly journals Synthesis and Properties of 6-Aryl-4-azidocinnolines and 6-Aryl-4-(1,2,3-1H-triazol-1-yl)cinnolines

Molecules ◽  
2019 ◽  
Vol 24 (13) ◽  
pp. 2386 ◽  
Author(s):  
Natalia A. Danilkina ◽  
Nina S. Bukhtiiarova ◽  
Anastasia I. Govdi ◽  
Anna A. Vasileva ◽  
Andrey M. Rumyantsev ◽  
...  
Keyword(s):  
Photoinduced Electron Transfer ◽  
Functional Group ◽  
Click Reaction ◽  
Bromine Atom ◽  
Photophysical Properties ◽  
Triazole Ring ◽  
Synthetic Approach ◽  
Terminal Alkynes ◽  
Reaction Products ◽  
Fluorescent Properties

An efficient approach towards the synthesis of 6-aryl-4-azidocinnolines was developed with the aim of exploring the photophysical properties of 6-aryl-4-azidocinnolines and their click reaction products with alkynes, 6-aryl-4-(1,2,3-1H-triazol-1-yl)cinnolines. The synthetic route is based on the Richter-type cyclization of 2-ethynyl-4-aryltriazenes with the formation of 4-bromo-6-arylcinnolines and nucleophilic substitution of a bromine atom with an azide functional group. The developed synthetic approach is tolerant to variations of functional groups on the aryl moiety. The resulting azidocinnolines were found to be reactive in both CuAAC with terminal alkynes and SPAAC with diazacyclononyne, yielding 4-triazolylcinnolines. It was found that 4-azido-6-arylcinnolines possess weak fluorescent properties, while conversion of the azido function into a triazole ring led to complete fluorescence quenching. The lack of fluorescence in triazoles could be explained by the non-planar structure of triazolylcinnolines and a possible photoinduced electron transfer (PET) mechanism. Among the series of 4-triazolylcinnoline derivatives a compound bearing hydroxyalkyl substituent at triazole ring was found to be cytotoxic to HeLa cells.

Green synthesis of triazolo-nucleoside conjugates via azide–alkyne C–N bond formation

2022 ◽  
Vol 0 (0) ◽  
Author(s):  
Rajesh Kumar ◽  
Jyotirmoy Maity ◽  
Divya Mathur ◽  
Abhishek Verma ◽  
Neha Rana ◽  
...  
Keyword(s):  
Click Reaction ◽  
Photophysical Properties ◽  
Bond Formation ◽  
Triazole Ring ◽  
Modified Nucleosides ◽  
Dipolar Cycloaddition ◽  
Efficient Tool ◽  
The Core ◽  
Therapeutic Value ◽  
Synthetic Methodologies

Abstract Modified nucleosides are the core precursors for the synthesis of artificial nucleic acids, and are important in the field of synthetic and medicinal chemistry. In order to synthesize various triazolo-compounds, copper and ruthenium catalysed azide–alkyne 1,3-dipolar cycloaddition reactions also known as click reaction have emerged as a facile and efficient tool due to its simplicity and convenient conditions. Introduction of a triazole ring in nucleosides enhances their therapeutic value and various photophysical properties. This review primarily focuses on the plethora of synthetic methodologies being employed to synthesize sugar modified triazolyl nucleosides, their therapeutic importance and various other applications.

Synthetic Routes for 1,4-disubstituted 1,2,3-triazoles: A Review

2019 ◽  
Vol 23 (8) ◽  
pp. 860-900 ◽  
Author(s):  
Chander P. Kaushik ◽  
Jyoti Sangwan ◽  
Raj Luxmi ◽  
Krishan Kumar ◽  
Ashima Pahwa
Keyword(s):  
Solid Phase ◽  
Click Reaction ◽  
Biological Activities ◽  
Triazole Ring ◽  
Copper Catalysts ◽  
Biologically Active ◽  
Pharmaceutical Chemistry ◽  
Biological Targets ◽  
Synthetic Routes ◽  
High Yields

N-Heterocyclic compounds like 1,2,3-triazoles serve as a key scaffolds among organic compounds having diverse applications in the field of drug discovery, bioconjugation, material science, liquid crystals, pharmaceutical chemistry and solid phase organic synthesis. Various drugs containing 1,2,3-triazole ring which are commonly available in market includes Rufinamide, Cefatrizine, Tazobactam etc., Stability to acidic/basic hydrolysis along with significant dipole moment support triazole moiety for appreciable participation in hydrogen bonding and dipole-dipole interactions with biological targets. Huisgen 1,3-dipolar azide-alkyne cycloaddition culminate into a mixture of 1,4 and 1,5- disubstituted 1,2,3-triazoles. In 2001, Sharpless and Meldal came across with a copper(I) catalyzed regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles by cycloaddition between azides and terminal alkynes. This azide-alkyne cycloaddition has been labelled as a one of the important key click reaction. Click synthesis describes chemical reactions that are simple to perform, gives high selectivity, wide in scope, fast reaction rate and high yields. Click reactions are not single specific reaction, but serve as a pathway for construction of simple to complex molecules from a variety of starting materials. In the last few decades, 1,2,3-triazoles attracted attention of researchers all over the world because of their broad spectrum of biological activities. Keeping in view the biological importance of 1,2,3-triazole, in this review we focus on the various synthetic routes for the syntheisis of 1,4-disubstituted 1,2,3-triazoles. This review involves various synthetic protocols which involves copper and non-copper catalysts, different solvents as well as substrates. It will boost synthetic chemists to explore new pathway for the development of newer biologically active 1,2,3-triazoles.

Synthesis of Novel 1,2,3-Triazole Derivatives of Isocoumarins and 3,4-Dihydroisocoumarin with Potential Antiplasmodial Activity In Vitro

2020 ◽  
Vol 16 ◽  
Author(s):  
Lucas da Silva Santos ◽  
Matheus Fillipe Langanke de Carvalho ◽  
Ana Claudia de Souza Pinto ◽  
Amanda Luisa da Fonseca ◽  
Julio César Dias Lopes ◽  
...  
Keyword(s):  
Triazole Ring ◽  
Antiplasmodial Activity ◽  
World Health ◽  
Dipolar Cycloaddition ◽  
Terminal Alkynes ◽  
The World ◽  
Ic50 Values ◽  
Derivatives Of ◽  
Active Substances

Background: Malaria greatly affects the world health, having caused more than 228 million cases only in 2018. The emergence of drug resistance is one of the main problems in its treatment, demonstrating the urge for the development of new antimalarial drugs. Objective: Synthesis and in vitro antiplasmodial evaluation of triazole compounds derived from isocoumarins and a 3,4- dihydroisocoumarin. Method: The compounds were synthesized in 4 to 6-step reactions with the formation of the triazole ring via the Copper(I)-catalyzed 1,3-dipolar cycloaddition between isocoumarin or 3,4-dihydroisocoumarin azides and terminal alkynes. This key reaction provided compounds with an unprecedented connection of isocoumarin or 3,4-dihydroisocoumarin and the 1,2,3-triazole ring. The products were tested for their antiplasmodial activity against a Plasmodium falciparum chloroquine resistant and sensitive strains (W2 and 3D7, respectively). Results: Thirty-one substances were efficiently obtained by the proposed routes with an overall yield of 25-53%. The active substances in the antiplasmodial test displayed IC50 values ranging from 0.68-2.89 μM and 0.85-2.07 μM against W2 and 3D7 strains, respectively.

The Azidosulfonylation of Terminal Alkynes Leading to β-azidovinyl Sulfones

2021 ◽  
Author(s):  
Long Zheng ◽  
Zhanjing Wang ◽  
Chen Li ◽  
Yong Wu ◽  
Zhaohong Liu ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Functional Group ◽  
High Yield ◽  
Terminal Alkynes

We reported herein the first example of N3 radical-mediated azidosulfonylation of alkynes, affording the β-azidovinyl sulfone products in broad substrate scope, excellent functional group compatibility, and high yield. DFT calculations...

scholarly journals Homocoupling of terminal alkynes catalyzed by CuCl under solvent-free conditions

2021 ◽  
pp. 174751982110325
Author(s):  
Yan Xiao ◽  
Jiyu Gao ◽  
Peng Chen ◽  
Guangliang Chen ◽  
Zicheng Li ◽  
...  
Keyword(s):  
Functional Group ◽  
Reaction Times ◽  
Environmentally Friendly ◽  
Solvent Free ◽  
Copper Salt ◽  
Terminal Alkynes ◽  
Mild Conditions ◽  
Solvent Free Conditions ◽  
Environmentally Friendly Process

A series of symmetrical 1,4-disubstituted buta-1,3-diynes is prepared with excellent yields (up to 95%) through homocoupling of terminal alkynes catalyzed by a copper salt under solvent-free conditions. This method provides an environmentally friendly process to prepare 1,3-diynes in short reaction times under mild conditions. Furthermore, the method is suitable for a wide substrate scope and has excellent functional group compatibility. The reaction can also be scaled up to gram level.

scholarly journals Clickable azide-functionalized bromoarylaldehydes – synthesis and photophysical characterization

2020 ◽  
Vol 16 ◽  
pp. 1683-1692 ◽  
Author(s):  
Dominik Göbel ◽  
Marius Friedrich ◽  
Enno Lork ◽  
Boris J Nachtsheim
Keyword(s):  
High Efficiency ◽  
Photophysical Properties ◽  
Covalent Attachment ◽  
Terminal Alkynes ◽  
Facile Synthesis ◽  
Triazole Derivatives ◽  
Emission Behavior ◽  
Substituted Benzaldehydes ◽  
Covalently Linked

Herein, we present a facile synthesis of three azide-functionalized fluorophores and their covalent attachment as triazoles in Huisgen-type cycloadditions with model alkynes. Besides two ortho- and para-bromo-substituted benzaldehydes, the azide functionalization of a fluorene-based structure will be presented. The copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) of the so-synthesized azide-functionalized bromocarbaldehydes with terminal alkynes, exhibiting different degrees of steric demand, was performed in high efficiency. Finally, we investigated the photophysical properties of the azide-functionalized arenes and their covalently linked triazole derivatives to gain deeper insight towards the effect of these covalent linkers on the emission behavior.

scholarly journals Silver-catalysed azide–alkyne cycloaddition (AgAAC): assessing the mechanism by density functional theory calculations

2016 ◽  
Vol 3 (9) ◽  
pp. 160090 ◽  
Author(s):  
Biswadip Banerji ◽  
K. Chandrasekhar ◽  
Sunil Kumar Killi ◽  
Sumit Kumar Pramanik ◽  
Pal Uttam ◽  
...  
Keyword(s):  
Density Functional ◽  
Click Reaction ◽  
Cycloaddition Reaction ◽  
Triazole Ring ◽  
Density Functional Theory Calculations ◽  
Dipolar Cycloaddition ◽  
Reaction Conditions ◽  
Functional Theory ◽  
Click Reactions ◽  
Counter Ions

‘Click reactions’ are the copper catalysed dipolar cycloaddition reaction of azides and alkynes to incorporate nitrogens into a cyclic hydrocarbon scaffold forming a triazole ring. Owing to its efficiency and versatility, this reaction and the products, triazole-containing heterocycles, have immense importance in medicinal chemistry. Copper is the only known catalyst to carry out this reaction, the mechanism of which remains unclear. We report here that the ‘click reactions’ can also be catalysed by silver halides in non-aqueous medium. It constitutes an alternative to the well-known CuAAC click reaction. The yield of the reaction varies on the type of counter ion present in the silver salt. This reaction exhibits significant features, such as high regioselectivity, mild reaction conditions, easy availability of substrates and reasonably good yields. In this communication, the findings of a new catalyst along with the effect of solvent and counter ions will help to decipher the still obscure mechanism of this important reaction.

Stabilization of Cu(0)-nanoparticles into the nanopores of modified montmorillonite: An implication on the catalytic approach for “Click” reaction between azides and terminal alkynes

2011 ◽  
Vol 13 (12) ◽  
pp. 3453 ◽  
Author(s):  
Bibek Jyoti Borah ◽  
Dipanka Dutta ◽  
Partha Pratim Saikia ◽  
Nabin Chandra Barua ◽  
Dipak Kumar Dutta
Keyword(s):  
Click Reaction ◽  
Terminal Alkynes ◽  
Modified Montmorillonite

scholarly journals Investigation of the Binding Affinity of a Broad Array of l-Fucosides with Six Fucose-Specific Lectins of Bacterial and Fungal Origin

Molecules ◽  
2019 ◽  
Vol 24 (12) ◽  
pp. 2262 ◽  
Author(s):  
Son Thai Le ◽  
Lenka Malinovska ◽  
Michaela Vašková ◽  
Erika Mező ◽  
Viktor Kelemen ◽  
...  
Keyword(s):  
Binding Affinity ◽  
Functional Group ◽  
Click Reaction ◽  
Inhibition Assay ◽  
Promising Candidate ◽  
Hemagglutination Inhibition Assay ◽  
Broad Array ◽  
Amine Functional Group ◽  
Potential Inhibitors ◽  
Better Than

Series of multivalent α-l-fucoside containing glycoclusters and variously decorated l-fucosides were synthesized to find potential inhibitors of fucose-specific lectins and study the structure-binding affinity relationships. Tri- and tetravalent fucoclusters were built using copper-mediated azide-alkyne click chemistry. Series of fucoside monomers and dimers were synthesized using various methods, namely glycosylation, an azide-alkyne click reaction, photoinduced thiol-en addition, and sulfation. The interactions between compounds with six fucolectins of bacterial or fungal origin were tested using a hemagglutination inhibition assay. As a result, a tetravalent, α-l-fucose presenting glycocluster showed to be a ligand that was orders of magnitude better than a simple monosaccharide for tested lectins in most cases, which can nominate it as a universal ligand for studied lectins. This compound was also able to inhibit the adhesion of Pseudomonas aeruginosa cells to human epithelial bronchial cells. A trivalent fucocluster with a protected amine functional group also seems to be a promising candidate for designing glycoconjugates and chimeras.

Multifunctionalized octamethoxy-[8]cycloparaphenylene: facile synthesis and analysis of novel photophysical and photoinduced electron transfer properties

2019 ◽  
Vol 6 (11) ◽  
pp. 1885-1890 ◽  
Author(s):  
Shengsheng Cui ◽  
Guilin Zhuang ◽  
Jinyi Wang ◽  
Qiang Huang ◽  
Shengda Wang ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Emission Spectrum ◽  
Photoinduced Electron Transfer ◽  
Photophysical Properties ◽  
Hypsochromic Shift ◽  
Facile Synthesis ◽  
Electron Transfer Properties ◽  
Transfer Properties

A novel multifunctionalized carbon nanoring was facilely synthesized, which demonstrates an unusual hypsochromic shift in the emission spectrum with interesting photophysical properties.

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