Refernces
10.1021/ja904604x
The research focuses on the total synthesis and structure-activity investigation of the marine natural product neopeltolide, a highly cytotoxic compound with potential anticancer properties. The study employs a key bond-forming step using Lewis acid-catalyzed intramolecular macrocyclization to simultaneously install a tetrahydropyran ring and a macrocycle. The researchers synthesized neopeltolide and its analogs to evaluate their biological activity against cancer cell lines, finding that neither the macrolide nor the oxazole side chain alone could inhibit cancer cell growth, but alterations to the ester side chain or macrolide stereochemistry resulted in a loss of biological activity. The synthesis involved various reactants, including 1,3-propanediol, ethyl 3-oxohexanoate, and methyl chloroformate, and utilized techniques such as Ti(i-OPr)4-catalyzed aldol reactions, Noyori reduction, and Stille coupling. The synthesized compounds were analyzed using 1D and 2D NMR spectroscopy, HRMS, and optical rotation to confirm their structures and assess their biological activity through cell proliferation assays.
10.1002/adfm.201103147
The research focuses on the development of a new family of cationic charged biocompatible hybrid hydrogels, based on arginine unsaturated poly(ester amide) (Arg-UPEA) and Pluronic diacrylate (Pluronic-DA), which were fabricated through UV photocrosslinking in an aqueous medium. The purpose of this study was to improve the cellular interactions of synthetic hydrogels for potential biomedical applications by introducing cationic Arg-UPEA, which possesses biocompatibility and cationic properties. The conclusions drawn from the research indicate that the incorporation of Arg-UPEA into Pluronic-DA hydrogels significantly enhanced cell attachment, proliferation, and viability of both Detroit 539 human fibroblasts and bovine aortic endothelial cells. The chemicals used in the process include Pluronic F127, acryloyl chloride, triethylamine, Irgacure 2959 (as a photoinitiator), L-arginine, p-toluenesulfonic acid monohydrate, fumaryl chloride, ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, and p-nitrophenol, among others. These chemicals were utilized in the synthesis of the hydrogel precursors and for the characterization of their physicochemical properties.
10.1016/S0040-4039(00)95573-4
The research focuses on the enantioselective functionalization of 2-substituted 1,3-propanediols using chiral spiroketals derived from E-menthone. The study explores two methods for the selective ring-cleavage reaction of spiroketals: one promoted by titanium tetrachloride and the other by triisobutylaluminum. Key chemicals involved in the research include E-menthone as the chiral auxiliary, triisobutylaluminum as the organoaluminum reagent, titanium tetrachloride, and various reagents for functional group transformations such as benzyl bromide, acetic anhydride, and lithium triethylborohydride. The methods were applied to the preparation of (S)-2,3-dimethylbutyl phenyl sulfide, a chiral starting material for the synthesis of brassinosteroids. The study highlights the complementary nature of the two ring-cleavage methods, with the triisobutylaluminum method allowing for the recovery of E-menthone and the preparation of chiral derivatives with benzyl or acyl groups that were not accessible by the previous titanium tetrachloride method.
10.1016/S0008-6215(00)84841-7
Phenylboronic anhydride (C6H5BO)2 is the key reactant in the formation of phenylboronic esters. It reacts with various diols and triols to form cyclic phenylboronic esters. It is solid at room temperature and highly reactive due to the presence of boron, which can form coordination bonds with the oxygen atoms in the alcohol. Pentane-1,3,5-triol (C5H12O3) is the main subject of this study. It reacts with phenylboronic anhydride to form specific phenylboronic ester structures. It is a polyol containing three hydroxyl groups at positions 1, 3, and 5, respectively, of the pentane backbone. These hydroxyl groups are reactive and can form coordination bonds with boron atoms. Propane-1,3-diol (C3H8O2) is a diol containing hydroxyl groups at positions 1 and 3, respectively, of the propane backbone. It is a liquid at room temperature and is used to compare the reactivity with other diols and triols. It is used as a reference diol to study the formation of phenylboronic esters. It reacts with phenylboronic anhydride to form cyclic phenylboronic esters. Pentane-1,5-diol (C5H12O2), a diol with hydroxyl groups at positions 1 and 5 of the pentane backbone. It is a liquid at room temperature and helps to understand the formation of larger ring structures. It is used to study the formation of phenylboronic esters. It reacts with phenylboronic anhydride to form cyclic phenylboronic esters. Hexane-1,6-diol (C6H14O2), a diol with hydroxyl groups at positions 1 and 6 of the hexane backbone. It is a liquid at room temperature and helps to understand the formation of larger ring structures. It is used to study the formation of phenylboronic esters. It reacts with phenylboronic anhydride to form cyclic phenylboronic esters.
