CuAAC-ensembled 1,2,3-triazole-linked isosteres as pharmacophores in drug discovery: review

Abstract

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, anti-diabetic, and anti-Alzheimer drugs.

Synthesis and In Vitro Cytotoxicity and Antibacterial Activity of Novel 1,2,3-Triazol-5-yl-Phosphonates

“…The 31 P, 1 H, 13 C, NMR spectra were taken in CDCl 3 solution on a Bruker AV-300 spectrometer operating at 121.5, 300 and 75.5 MHz, respectively. Chemical shifts are downfield relative to 85% H 3 PO 4 and TMS.…”

“…In the last decades, 1,2,3-triazoles have received significant attention due to the wide range of their possible applications in materials science, biochemistry or even in drug design [8][9][10]. Compounds containing the 1,2,3-triazole scaffold may have versatile biological activities, such as antibacterial, antiviral, antifungal, anticancer or anti-inflammatory effects [11][12][13]. Some novel triazole-based heterocycles showed activity against bacterial strains (Bacillus subtilis and Escherichia coli) [14][15][16], and in vitro cytotoxicity against tumor cell lines HL-60 (myeloid leukemia), MCF-7 (breast cancer), A549 (lung cancer) and HCT-116 (colon cancer) [17][18][19].…”

Synthesis and Biological Evaluation of a Library of AGE‐Related Amino Acid Triazole Crosslinkers

“…click reaction) and Cu‐ or azide‐free alternatives. [1e], [1f] Furthermore, their possibility to form CH‐π interactions to generate mesoionic carbenes makes them attractive as ligands to coordinate both metal ions as well as biological matter such as enzymes. In addition, the use of triazoles for the isosteric replacement of amides allows their use as pharmacophoric subunits in biologically active compounds and drugs .…”

“…[1e], [1f] Furthermore, their possibility to form CH‐π interactions to generate mesoionic carbenes makes them attractive as ligands to coordinate both metal ions as well as biological matter such as enzymes. In addition, the use of triazoles for the isosteric replacement of amides allows their use as pharmacophoric subunits in biologically active compounds and drugs . The corresponding triazolium cations were employed as functional ionic liquids, precursors of mesoionic carbenes, and building blocks of supramolecular assemblies .…”

“…Therefore, we anticipated that synthetic AGEs carrying a triazolium core instead of the imidazolium unit might be a promising alternative, because they should be readily available by Cu‐catalyzed click reaction of amino acid‐derived alkynes and azides, respectively. [1h] It was therefore our aim to provide a library of AGE analogs, carrying a central triazole 12 or triazolium unit 12‐MeX rather than an imidazolium unit. Moreover, the possibility for N ‐alkylation enables the comparison of charged and neutral crosslinkers and broadens the scope regarding structure‐activity relationship (SAR) studies.…”