10-Phthalimidocamphor oxime was prepared from easily available 10-iodocamphor in two steps. Reduction of the oxime functionality resulted in the formation of two novel polycyclic isoindolinone ...heterocycles, the attempted preparation of the primary amine failed. The structures of novel heterocycles were unambiguously confirmed by single crystal X-ray diffraction as well as NMR techniques.
The synthesis of two novel (+)-isocampholenic acid-derived amines has been realized starting from commercially available (1
S
)-(+)-10-camphorsulfonic acid. The novel amines as well as ...(+)-isocampholenic acid have been used as building blocks in the construction of a library of amides using various aliphatic, aromatic, and amino acid-derived coupling partners using BPC and CDI as activating agents. Amide derivatives have been assayed against several enzymes that hold potential for the development of new drugs to battle bacterial infections and Alzheimer’s disease. Compounds
20c
and
20e
showed promising selective sub-micromolar inhibition of human butyrylcholinesterase
(
h
BChE
)
(
IC
50
values
0.80
±
0.05
and
0.25
±
0.02
μ
M
, respectively).
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