Mechanistic insights into lysine-targeting covalent inhibition through a theoretical study of ester aminolysis

Development of targeted covalent inhibitors in drug design has a broad and important interest and many efforts are currently being made in this direction. Targeted covalent inhibitors have special relevance...

6-Halo-2-pyridone as an efficient organocatalyst for ester aminolysis

6-Halo-2-pyridones effectively catalyse ester aminolysis as bifunctional catalysts. This reaction did not require any special conditions and was operationally convenient.

Thermally Reversible Polymeric Networks from Vegetable Oils

Low cross-link density thermally reversible networks were successfully synthesized from jatropha and sunflower oils. The oils were epoxidized and subsequently reacted with furfurylamine to attach furan groups onto the triglycerides, preferably at the epoxide sites rather than at the ester ones. Under the same reaction conditions, the modified jatropha oil retained the triglyceride structure more efficiently than its sunflower-based counterpart, i.e., the ester aminolysis reaction was less relevant for the jatropha oil. These furan-modified oils were then reacted with mixtures of aliphatic and aromatic bismaleimides, viz. 1,12-bismaleimido dodecane and 1,1′-(methylenedi-4,1-phenylene)bismaleimide, resulting in a series of polymers with Tg ranging between 3.6 and 19.8 °C. Changes in the chemical structure and mechanical properties during recurrent thermal cycles suggested that the Diels–Alder and retro-Diels–Alder reactions occurred. However, the reversibility was reduced over the thermal cycles due to several possible causes. There are indications that the maleimide groups were homopolymerized and the Diels–Alder adducts were aromatized, leading to irreversibly cross-linked polymers. Two of the polymers were successfully applied as adhesives without modifications. This result demonstrates one of the potential applications of these polymers.

Synthesis of cyclic peptide disulfide–PHPMA conjugates via sequential active ester aminolysis and CuAAC coupling

A synthetic strategy for the preparation of cyclic peptide disulfide–polymer conjugates that does not require peptide protecting groups is reported.

Synthesis, Characterization, and Drug Encapsulation of Hyperbranched Polyamidoamine Modified by β-Cyclodextrin

h-PAMAM-COOMe and its β-CD derivatives (h-PAMAM-CD) were synthesized step by step via the Michael addition and ester-aminolysis reaction from hyperbranched polyamidoamine (h-PAMAM). The structures of the as-prepared polymers were confirmed by Ubbelohde viscometer, FTIR, and 1H NMR. A series of inclusion complexation formed by β-naphtol in increasing h-PAMAM-β-CD with different concerntration were investigated by UV-vis spectrometer. The result showed that the novel hyperbranched polymer might have potential applications as delivery materials in chemotherapy.