I)-catalyzed azide-alkyne cycloaddition (CuAAC) became one of the most effective and reliable synthetic tools in diverse areas of modern chemistry, such as organic, medicinal and polymer chemistry, material science and chemical biology. The advantages of this reaction are high selectivity, simple reaction conditions, wide scope and excellent functional group tolerance. This efficient transformation can be used for the synthesis of various 1,2,3triazoles. On the other hand, CuAAC can be efficiently used for bioconjugation of two units bearing alkyne and azide functions via the triazole moiety. Moreover, the use of azides and alkynes bearing orthogonal functional groups in this reaction opens broad opportunities for the synthesis of valuable polyfunctionalized triazole-containg molecules. Thus, the initial discussion is focused on synthetic applications of functionally substituted azides and terminal alkynes in the CuAAC, combined with other transformations.The prominent part of this review is devoted to an application of these bi (or tri)-functional reagents for the design, synthesis or labeling of biologically active molecules.
Chiral scaffolds combining isocyanide and azide groups can be effectively synthesized to permit the efficient construction of both amino (hydroxy) acids and triazole derivatives, which
We
identified and explored the structure–activity-relationship
(SAR) of an adamantane carboxamide chemical series of Ebola virus
(EBOV) inhibitors. Selected analogs exhibited half-maximal inhibitory
concentrations (EC50 values) of ∼10–15 nM
in vesicular stomatitis virus (VSV) pseudotyped EBOV
(pEBOV) infectivity assays, low hundred nanomolar EC50 activity
against wild type EBOV, aqueous solubility >20 mg/mL, and attractive
metabolic stability in human and nonhuman liver microsomes. X-ray
cocrystallographic characterizations of a lead compound with the EBOV
glycoprotein (GP) established the EBOV GP as a target for direct compound
inhibitory activity and further provided relevant structural models
that may assist in identifying optimized therapeutic candidates.
A conjugation of bile acids with peptides via Cu(I)-catalyzed click chemistry has been described. Novel bile acid-peptide conjugates linked via a 1,2,3-triazole moiety based on cholic, deoxycholic and lithocholic acid derivatives were synthesized using Cu(I)-catalyzed 1,3-dipolar cycloaddition ("click" reaction). It was shown that up to three peptide fragments can be attached to a central steroid core, thus forming complex three-dimensional polyconjugate structures, which can find important applications in biochemistry, medicinal chemistry, and coordination chemistry.
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