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1 article(s) from Finch, Angela

Vicinal difluorination as a C=C surrogate: an analog of piperine with enhanced solubility, photostability, and acetylcholinesterase inhibitory activity

Yuvixza Lizarme-Salas,
Alexandra Daryl Ariawan,
Ranjala Ratnayake,
Hendrik Luesch,
Angela Finch and
Luke Hunter

Beilstein J. Org. Chem. 2020, 16, 2663–2670, doi:10.3762/bjoc.16.216

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Figure 1: The natural product piperine (1) is the inspiration for this work; the crystal structure is shown [14]....

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Scheme 1: The attempted synthesis of 6 (a diastereoisomer of 2) via a one-step 1,2-difluorination reaction [24]. ...

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Scheme 2: The attempted synthesis of 2 via a stepwise fluorination approach (ether series). THF = tetrahydrof...

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Scheme 3: Synthesis of compound 2 via a stepwise fluorination approach (ester series). DIC = diisopropylcarbo...

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Figure 2: Conformational analysis of 2 by DFT and NMR. The numbering scheme for NMR spins is given on structu...

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Figure 3: Analog 2 has greater stability to UV light than does piperine (1).

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Figure 4: Biological activity of piperine (1) and derivative 2. (a) Inihbition of AChE by 1 (IC₅₀ >1000 μM) a...

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Published 28 Oct 2020

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