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Beilstein J. Org. Chem. 2020, 16, 2663–2670, doi:10.3762/bjoc.16.216
Graphical Abstract
Figure 1: The natural product piperine (1) is the inspiration for this work; the crystal structure is shown [14]....
Scheme 1: The attempted synthesis of 6 (a diastereoisomer of 2) via a one-step 1,2-difluorination reaction [24]. ...
Scheme 2: The attempted synthesis of 2 via a stepwise fluorination approach (ether series). THF = tetrahydrof...
Scheme 3: Synthesis of compound 2 via a stepwise fluorination approach (ester series). DIC = diisopropylcarbo...
Figure 2: Conformational analysis of 2 by DFT and NMR. The numbering scheme for NMR spins is given on structu...
Figure 3: Analog 2 has greater stability to UV light than does piperine (1).
Figure 4: Biological activity of piperine (1) and derivative 2. (a) Inihbition of AChE by 1 (IC50 >1000 μM) a...