Syntheses and antibacterial activities of 4 linear nonphenolic diarylheptanoids.

Four linear nonphenolic diarylheptanoids were synthesized and their antibacterial activities were studied. ( )-2-Me-CBS-catalysed reduction of alnustone with BHSMe gave ( )(-)(4 ,6 )-1,7-diphenylhepta-4,6-dien-3-ol, a natural product. Reduction of alnustone with Na in -BuOH at -15 °C under N atm gave ()-1,7-diphenylhept-5- en-3-one as a Birch-type reduction product.

Disassembly of polymeric nanoparticles with enzyme-triggered polymer unzipping: polyelectrolyte complexes vs. amphiphilic nanoassemblies.

Alkaline phosphatase (ALP) responsive polymers, which can unzip from head to tail are reported. Hydrophilic and hydrophobic modification of the polymer was carried out for the formation of a polyelectrolyte complex and an amphiphilic nanoassembly, respectively, which offered distinct enzyme-triggered disassembly kinetics.

Propagation of Enzyme-Induced Surface Events inside Polymer Nanoassemblies for a Fast and Tunable Response.

We report a new molecular design strategy that allows for the propagation of surface enzymatic events inside a supramolecular assembly for accelerated molecular release. The approach addresses a key shortcoming encountered with many of the currently available enzyme-induced disassembly strategies, which rely on the unimer-aggregate equilibria of amphiphilic assemblies. The enzymatic response of the host to predictably tune the kinetics of guest-molecule release can be programmed by controlling substrate accessibility through electrostatic complexation with a complementary polymer.

Photoactivation of Ligands for Extrinsically and Intrinsically Triggered Disassembly of Amphiphilic Nanoassemblies.

Specific response to the concurrent presence of two different inputs is one of the hallmarks of incorporating specificities in nature. Artificial nanoassemblies that concurrently respond to two very different inputs are of great interest in a variety of applications, especially in biomedicine. Here, we present a design strategy for amphiphilic nanoassemblies with such capabilities, enabled by photocaging a ligand moiety that is capable of binding to a specific protein.

Syntheses and evaluation of multicaulin and miltirone-like compounds as antituberculosis agents.

Four multicaulin and miltirone-like phenanthrene derivatives were synthesised and evaluated as antituberculosis agents. The crucial step of the synthesis was Pschorr coupling of 4-(3-isopropyl-4-methoxyphenyl)-2-(2-aminophenyl)ethane (13) to give 2-isopropyl-3-methoxy-9,10-dihydrophenanthrene (9) and 4-isopropyl-3-methoxy-9,10-dihydrophenanthrene (9a). Compound 9 was converted to multicaulin and miltirone-like phenanthrene derivatives by further reactions.

Total syntheses of multicaulins via oxidative photocyclization of stilbenes.

The Wittig reaction of 3-isopropyl-4-methoxybenzaldehyde and 2,3-dimethylbenzylphosphonium bromide afforded the corresponding stilbene mixture 16. Oxidative photocyclization of stilbene 16 with iodine facilitated the first total synthesis of 7-isopropyl-6-methoxy-1,2-dimethylphenanthrene, multicaulin (1). The O-demethylation of 1 with BBr3 afforded the 7-isopropyl-1,2-dimethylphenanthren-6-ol, O-demethylmulticaulin (2).