Macrocycles: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

Introduction: A cyclic compound is common motif in natural product structures. Cyclic peptides, a vast subset of natural products, display a wide variety of biological activities. Owing to their size, cyclic peptides are particularly attractive scaffolds for interrogating challenging biomolecular interactions, such as those at protein–protein interfaces. Methods and Results: This review takes an overview of the literature for the synthesis of peptide and non-peptide macrocycles, concentrating on advances in the last five years up to the end of 2017. These methods are clustered by strategies for preparation and further derivatization of preformed macrocycle-containing building blocks. Examples of the use of macrocycles in medicinal chemistry are reported, including a collation of macrocycle derivatives appearing in recent patents for medicinal chemistry applications. Conclusions: This review aims to provide an overview of the extensive recent studies involving macrocycles in synthesis and medicinal chemistry and to highlight the continuing challenges

Concise Synthesis of Macrocycles by Multicomponent Reactions

A short reaction pathway was devised to synthesize a library of artificial 18-27-membered macrocycles. The five-step reaction sequence involves ring opening of a cyclic anhydride with a diamine, esterification, coupling with an amino acid isocyanide, saponification, and, finally, macro-ring closure using an Ugi or, alternatively, a Passerini multicomponent reaction. Three out of the five steps allow for the versatile introduction of linker elements, side chains, and substituents with aromatic, heteroaromatic, and aliphatic character. The versatile pathway is described for 15 different target macrocycles on a mmol scale. Artificial macrocycles have recently become of great interest due to their potential to bind to difficult post-genomic targets

Sulfonated organic heteropolyacid salts as a highly efficient and green solid catalysts for the synthesis of 1,8-dioxo-decahydroacridine derivatives in water

AbstractIn the present study, we introduce two nonconventional ionic liquids [MIMPS]3PW12O40 (a) and [TEAPS]3PW12O40 (b) as green and highly efficient solid acid catalysts for the synthesis of 1,8-dioxo-decahydroacridine derivatives. The one-pot three component reaction of 1,3-cyclohexanediones, aromatic aldehydes and aromatic amines or ammonium acetate in water afforded the corresponding 1,8-dioxo-decahydroacridines in excellent yields. This reaction has been carried out in the presence of 1mol% of catalysts at room temperature. The reusability of the catalysts was demonstrated by a five-run test. Additionally, the catalysts pose several advantages including mild reaction conditions, cleaner reactions and shorter reaction times

Sensitive and selective electrochemical detection of bisphenol A based on SBA-15 like Cu-PMO modified glassy carbon electrode

This work reports the electrochemical detection of bisphenol A (BPA) using a novel and sensitive electrochemical sensor based on the Cu functionalized SBA-15 like periodic mesoporous organosilica-ionic liquid composite modified glassy carbon electrode (Cu@TU-PMO/IL/GCE). The structural morphology of Cu@TU-PMO is characterized by X-ray powder diffraction (XRD), energy dispersive X-ray analysis (EDX), Fourier transform infrared spectroscopy (FT-IR), transmission electron microscopy (TEM), Field emission scanning electron microscopy (FESEM), and Brunauer-Emmett-Teller (BET). The catalytic activity of the modified electrode toward oxidation of BPA was interrogated with cyclic voltammetry (CV) and differential pulse voltammetry (DPV) in phosphate buffer solution (pH 7.0) using the fabricated sensor. The electrochemical detection of the analyte was carried out at a neutral pH and the scan rate studies revealed that the sensor was stable. Under the optimal conditions, a linear range from 5.0 nM to 2.0 mu M and 4.0 to 500 mu M for detecting BPA was observed with a detection limit of 1.5 nM (S/N = 3). The sensor was applied to detect BPA in tap and seawater samples, and the accuracy of the results was validated by high-performance l