Comparative analysis of the trypanocidal activity and chemical properties of E-lychnophoric acid and its derivatives using theoretical calculations
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Abstract
blood forms of Trypanosoma cruzi at the concentrations of 13.86, 5.68, and 6.48 μg/mL, respectively.
Conformational distribution calculations (AM1) of 1, 2 and 3 gave minimum energies for the conformers
a, b, c, and d, which differ from each other only in the cyclononene ring geometry. Calculations (DFT/
BLYP/6-31G*) of geometry optimization and chemical properties were performed for conformers of 1, 2,
and 3. The theoretical results were numerically compared to the trypanocidal activity. Calculated values
of atomic charge, orbital population, and vibrational frequencies showed that the C-4–C-5 π-endocyclic
bond does not affect the trypanocidal activity of the studied compounds. Nevertheless, the structure of
the group at C-4 strongly influences the activity. However, the theoretical results indicated that the intra-
ring (C-1 and C-9) and π-exocycle (C-8 and C-14) carbons of caryophyllene-type structures promote
the trypanocidal activity of these compounds.
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