Journal ArticleDOI
Amide-1,2,3-triazole bioisosterism: the glycogen phosphorylase case
Evangelia D. Chrysina,Éva Bokor,K.-M. Alexacou,Maria Despoina Charavgi,George N. Oikonomakos,Spyros E. Zographos,Demetres D. Leonidas,Nikos G. Oikonomakos,László Somsák +8 more
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TLDR
In this paper, the same azide and substituted acetylenes gave 1-(β-d -glucopyranosyl)-4-substituted-1,2,3-triazoles in Cu(I)-catalyzed azide-alkyne cycloadditions.Abstract:
Per-O-acetylated β- d -glucopyranosyl azide was transformed into an intermediate iminophosphorane by PMe 3 which was then acylated to N -acyl-β- d -glucopyranosylamines. The same azide and substituted acetylenes gave 1-(β- d -glucopyranosyl)-4-substituted-1,2,3-triazoles in Cu(I)-catalyzed azide–alkyne cycloadditions. Deprotection of these products by the Zemplen method furnished β- d -Glc p -NHCO-R derivatives as well as 1-(β- d -Glc p )-4-R-1,2,3-triazoles which were evaluated as inhibitors of rabbit muscle glycogen phosphorylase b. Pairs of amides versus triazoles with the same R group displayed similar inhibition constants. X-ray crystallographic studies on the enzyme–inhibitor complexes revealed high similarities in the binding of pairs with R = 2-naphthyl and hydroxymethyl, while for the R = Ph and 1-naphthyl compounds a different orientation of the aromatic part and changes in the conformation of the 280s loop were observed. By this study new examples of amide-1,2,3-triazole bioisosteric relationship have been provided.read more
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Journal ArticleDOI
Click Chemistry for Drug Development and Diverse Chemical–Biology Applications
Journal ArticleDOI
The 1,2,3-triazole ring as a bioisostere in medicinal chemistry
Elisa Bonandi,Michael S. Christodoulou,Gaia Fumagalli,Dario Perdicchia,Giulio Rastelli,Daniele Passarella +5 more
TL;DR: An overview of the 1,2,3-triazole ring as a bioisostere for the design of drug analogs, highlighting relevant recent examples.
Journal ArticleDOI
Synthesis of novel sulfanilamide-derived 1,2,3-triazoles and their evaluation for antibacterial and antifungal activities.
TL;DR: 4-amino-N-((1-dodecyl-1H-1,2,3-triazol-4-yl)methyl) benzenesulfonamide were found to be the most potent compounds against all the tested strains except for Candida albicans and Candida mycoderma.
Journal ArticleDOI
Amide Bond Bioisosteres: Strategies, Synthesis, and Successes
TL;DR: The strategic decisions in selecting an amide bioisostere (the why), synthetic routes to each (the how) and success stories of each bioisosterism (the implementation) are reviewed to provide a comprehensive overview of this important toolbox for medicinal chemists.
Journal ArticleDOI
CuAAC-ensembled 1,2,3-triazole-linked isosteres as pharmacophores in drug discovery: review
TL;DR: The review lays emphasis on the significance of 1,2,3-triazoles synthesized via CuAAC reaction having potential to act as anti-microbial, anti-cancer, anti’viral,Anti-inflammatory,anti-tuberculosis, pro-diabetic, and anti-Alzheimer drugs.
References
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Book ChapterDOI
Processing of X-ray diffraction data collected in oscillation mode
Zbyszek Otwinowski,Wladek Minor +1 more
TL;DR: The methods presented in the chapter have been applied to solve a large variety of problems, from inorganic molecules with 5 A unit cell to rotavirus of 700 A diameters crystallized in 700 × 1000 × 1400 A cell.
Journal ArticleDOI
MOLSCRIPT: a program to produce both detailed and schematic plots of protein structures
TL;DR: The MOLSCRIPT program as discussed by the authors produces plots of protein structures using several different kinds of representations, including simple wire models, ball-and-stick models, CPK models and text labels.
Journal ArticleDOI
The growing impact of click chemistry on drug discovery.
TL;DR: The copper-(I)-catalyzed 1,2,3-triazole formation from azides and terminal acetylenes is a particularly powerful linking reaction, due to its high degree of dependability, complete specificity, and the bio-compatibility of the reactants.
Journal ArticleDOI
Bioisosterism: A Rational Approach in Drug Design.
George Patani,Edmond J. LaVoie +1 more
TL;DR: This topic has been reviewed in previous years and the objective of this review is to provide an overview of bioisosteres that incorporates sufficient detail to enable the reader to understand the concepts being delineated.
Journal ArticleDOI
The growing applications of click chemistry
John E. Moses,Adam D. Moorhouse +1 more
TL;DR: This tutorial review examines the copper(I)-catalysed 1,2,3-triazole forming reaction between azides and terminal alkynes, which has become the gold standard of click chemistry due to its reliability, specificity and biocompatibility.