Steroid/Triterpenoid Functional Molecules based on “Click Chemistry”

Abstract

On the occasion of the 10th anniversary of click chemistry FOCUS REVIEWSAbstract: This Focus Review highlights the design and synthesis of various functional molecules based on steroid/triterpenoid as building blocks through the coppercatalyzed azide-alkyne cycloaddition (CuAAC) "click" reaction, as well as their applications in bioactivity, recognition, and assembly. This method shows great promise to allow us to develop novel molecules with characteristic functions using the CuAAC "click" reaction.

Recent syntheses of steroid derivatives using the CuAAC “click” reaction

“…This new compound 17 is a tweezer-type molecule with deoxycholic acid, 8-aminoquinoline, and 1,2,3triazole moieties. The 1,2,3-triazole moiety obtained via click chemistry allows the introduction of various functionalities and is a potential binding site for both metal ions and anions, 36,37 which is very useful for multitarget analysis. The click reaction between steroidal diazides 15 38 and quinoline terminal alkyne 16 39 led to the fluorescent probe 17 (Scheme 5).…”

A novel and simple solvent-dependent fluorescent probe based on a click generated 8-aminoquinoline–steroid conjugate for multi-detection of Cu(ii), oxalate and pyrophosphate

“…42 And 8-aminoquinoline and its derivatives are well-known excellent building blocks for constructing highly selective uorescent sensors of transition metal cations. 36,[43][44][45][46] Meanwhile, the bridging 1,2,3-triazole group was introduced via click chemistry in order to offer not only a straightforward strategy for the linkage of various functionalities, but also a potential binding site for both metal ions and anions, 47,48 which is very benecial for multi-target analysis.…”

Triterpenoid‐Based Self‐Healing Supramolecular Polymer Hydrogels Formed by Host–Guest Interactions

“…Generally, they consist of six isoprene units with multiple functional groups, unique chiral centers, rigid skeletons, and good biocompatibility. These features not only endow them with pharmacological properties, but also make them ideal building blocks for self‐assembling versatile supramolecular structures . Since the first supramolecular organogel based on a pentacyclic triterpenoid was reported by Bag and co‐workers in 2005, a series of pentacyclic triterpenoid‐based small molecules have been designed and synthesized to study their supramolecular gelation behavior .…”

“…[1][2][3][4][5] Generally,t hey consist of six isoprene units with multiple functional groups, unique chiral centers, rigids keletons, and good biocompatibility.T hese features not only endow them with pharmacological properties, [6][7][8][9] but also make them ideal building blocks fors elf-assembling versatile supramolecular structures. [10][11][12][13] Since the first supramolecular organogel based on ap entacyclic triterpenoid was reported by Bag and co-workers in 2005, [14] as eries of pentacyclic triterpe-noid-based smallm olecules have been designed and synthesized to study their supramolecular gelation behavior. [15][16][17][18][19][20][21][22][23][24] For example, Mezzenga et al reported that the right-handedf ibrillar networks in the hydrogel of glycyrrhizic acid could be utilized as scaffolds for hybrid nanomaterials in heterogeneous catalysis.…”