Click reaction based synthesis, antimicrobial, and cytotoxic activities of new 1,2,3-triazoles

Aly, Moustafa H.; Saad, Hosam A.; Mohamed, Mosselhi A. M.

doi:10.1016/j.bmcl.2015.04.096

Cited by 52 publications

(24 citation statements)

References 59 publications

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“…The target cholesterol–chalcone conjugates 6a–c and 7a,b were prepared by reacting 3β-azidocholest-5-ene ( 3 ) with propargylated chalcones 4a–c and 5a , b [ 24 ] under CuAAC conditions [ 35 ]. The reactions proceeded fairly in gently refluxing THF/H 2 O mixture containing L-ascorbic acid as reducing agent and a catalytic amount of CuSO 4 ·5H 2 O.…”

Section: Resultsmentioning

confidence: 99%

“…The second set of cholesterol conjugates ( Scheme 2 and Scheme 3 ) was prepared by CuAAC of (3β)-3-(prop-2-yn-1-yloxy)cholest-5-ene ( 10 ) with azidoalcanols 9a , b [ 24 ] and 3β-azidocholest-5-ene ( 3 ). These investigations aimed to address whether the terminal surface recognition glycon tag was necessary to stimulate the biological activity of triazolocholesterol [ 24 ] or just an alternative unique OH group, as in conjugates 11a , b , or even without it as in derivatives 12 and 13 , can retain its activity. Particularly, hydroxyalkyl-1,2,3-triazoles were reported as valuable pharmacophores [ 36 ].…”

Section: Resultsmentioning

confidence: 99%

“…Then, attention was given to prepare conjugate 24 ( Scheme 5 ). This is to investigate the pharmacological effects of the maltose tag compared with glucose as previously investigated in the case of VI [ 24 ]. Thus, coupling of glycosyl donor 21 [ 41 ] with acceptor 9a afforded maltoside 22 in low yield ( Scheme 5 ).…”

Section: Resultsmentioning

confidence: 99%

“…To investigate, whether the triazole or the cholesterol entities are not compatible with these debenzylation conditions, probes 36 and 38 ( Scheme 7 ) were prepared by CuAAC of derivative 34 with compounds 35 and 9b , respectively [ 24 ].…”

Section: Resultsmentioning

confidence: 99%

“…In light of this emerging propensity of cholesterol-based architectures to assimilate a plenty of pharmacological activities, cholesterol was propargylated, then reacted with azido-modified quinoline and glucopyranosyl derivatives as part of a previous study [ 24 ] to discover new antimicrobial and cytotoxic lead structures. Cholesterol conjugate VI ( Fig.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners

Aly¹,

Saad²,

Abdel‐Hafez³

2015

Beilstein J. Org. Chem.

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Summary3β-Azidocholest-5-ene (3) and (3β)-3-(prop-2-yn-1-yloxy)cholest-5-ene (10) were prepared as substrates to synthesize a variety of three-motif pharmacophoric conjugates through CuAAC. Basically, these conjugates included cholesterol and 1,2,3-triazole moieties, while the third, the pharmacophore, was either a chalcone, a lipophilic residue or a carbohydrate tag. These compounds were successfully prepared in good yields and characterized by NMR, MS and IR spectroscopic techniques. Chalcone conjugate 6c showed the best antimicrobial activity, while the lactoside conjugate 27 showed the best cytotoxic effect in vitro.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners

Aly¹,

Saad²,

Abdel‐Hafez³

2015

Beilstein J. Org. Chem.

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Cu₂O/reduced graphene oxide/TiO₂nanomaterial: An effective photocatalyst for azide‐alkyne cycloaddition with benzyl halides or epoxide derivatives under visible light irradiation

Mirza‐Aghayan

Saeedi

Boukherroub

2020

Applied Organom Chemis

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Cu 2 O/reduced graphene oxide/TiO 2 (Cu 2 O/rGO/TiO 2) photocatalyst was synthesized under ultrasonic irradiation. The nanomaterial was identified by scanning electron microscopy (SEM), transmission electron microscopy (TEM), Xray diffraction (XRD), Raman spectroscopy, X-ray photoelectron spectroscopy (XPS), Fourier transform infrared (FT-IR) spectroscopy, UV-vis absorption, and inductively coupled plasma optical emission spectroscopy (ICP-OES). The Cu 2 O/rGO/TiO 2 photocatalyst was utilized in "click" reaction for the preparation of 1,4-disubstituted 1,2,3-triazoles via one pot multicomponent reaction of benzyl halide or epoxide derivatives with alkynes in presence of NaN 3 and triethylamine under visible light irradiation. The "click" reaction was performed under mild conditions affording good to excellent yields of the triazole compounds using low catalyst loading in short reaction times. The nanocomposite was recovered and recycled for five successive runs without a major diminution in its catalytic performance.

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Trends in the Diversification of the Detergentome

Wycisk,

Wagner,

Urner

2023

ChemPlusChem

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Detergents are amphiphilic molecules that serve as enabling steps for today’s world applications. The increasing diversity of the detergentome is key to applications enabled by detergent science. Regardless of the application, the optimal design of detergents is determined empirically, which leads to failed preparations, and raising costs. To facilitate project planning, here we review synthesis strategies that drive the diversification of the detergentome. Synthesis strategies relevant for industrial and academic applications include linear, modular, combinatorial, bio‐based, and metric‐assisted detergent synthesis. Scopes and limitations of individual synthesis strategies in context with industrial product development and academic research are discussed. Furthermore, when designing detergents, the selection of molecular building blocks, i.e., head, linker, tail, is as important as the employed synthesis strategy. To facilitate the design of safe‐to‐use and tailor‐made detergents, we provide an overview of established head, linker, and tail groups and highlight selected scopes and limitations for applications. It becomes apparent that most recent contributions to the increasing chemical diversity of detergent building blocks originate from the development of detergents for membrane protein studies. The overview of synthesis strategies and molecular blocks will bring us closer to the ability to predictably design and synthesize optimal detergents for challenging future applications.

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Click reaction based synthesis, antimicrobial, and cytotoxic activities of new 1,2,3-triazoles

Cited by 52 publications

References 59 publications

Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners

Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners

Cu₂O/reduced graphene oxide/TiO₂nanomaterial: An effective photocatalyst for azide‐alkyne cycloaddition with benzyl halides or epoxide derivatives under visible light irradiation

Trends in the Diversification of the Detergentome

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Click reaction based synthesis, antimicrobial, and cytotoxic activities of new 1,2,3-triazoles

Cited by 52 publications

References 59 publications

Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners

Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners

Cu2O/reduced graphene oxide/TiO2nanomaterial: An effective photocatalyst for azide‐alkyne cycloaddition with benzyl halides or epoxide derivatives under visible light irradiation

Trends in the Diversification of the Detergentome

Contact Info

Product

Resources

About

Cu₂O/reduced graphene oxide/TiO₂nanomaterial: An effective photocatalyst for azide‐alkyne cycloaddition with benzyl halides or epoxide derivatives under visible light irradiation