Dipeptidyl peptidase IV (DPP4) inhibitors are emerging as a new class of therapeutic agents for the treatment of type 2 diabetes. They exert their beneficial effects by increasing the levels of active glucagon-like peptide-1 and glucose-dependent insulinotropic peptide, which are two important incretins for glucose homeostasis. Starting from a high-throughput screening hit, we were able to identify a series of piperidinone- and piperidine-constrained phenethylamines as novel DPP4 inhibitors. Optimized compounds are potent, selective, and have good pharmacokinetic profiles.
This paper describes a demonstration and a straightforward experiment using the guided-inquiry approach for the "like dissolves like" principle that is implemented at the beginning of the academic year. This experiment extends the students' understanding of the concept of solubility of organic molecules and its relationship to chemical structure. It is also a stepping stone to their comprehension of separation techniques for organic compounds. The objective of this experiment is to observe how the solubility of alcohols varies in water, acetone, or hexane. This approach allows students to integrate different concepts of organic chemistry learned throughout the general chemistry course. These concepts include: covalent bond, dipole moment, molecular geometry, intermolecular forces, and solubility.
The asymmetric allenylboration of representative aldehydes with the stable, storable 1 is reported. Easily and efficiently prepared in either enantiomeric form from the air-stable crystalline 4 through simple Grignard procedures, 1 gives 6 cleanly. The latter is easily isolated in high yield and ee with predictable stereochemistry. The procedure also regenerates 4 for its direct conversion back to 1 and facilitates the efficient recovery of the pseudoephedrine. The net process is the synthetic equivalent of the asymmetric addition of allenylmagnesium bromide to aldehydes. [reaction: see text]
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