Synthesis, Activity, and QSAR Studies of Tryptamine Derivatives on Third-instar Larvae of Aedes Aegypti Linn
Rafael R.B. Oliveira, Thaysnara B. Brito, Angelita Nepel, Emmanoel V. Costa, Andersson Barison, Rogeria S. Nunes, Roseli L.C. Santos and Socrates C.H. Cavalcanti
Affiliation: Medicinal Chemistry Laboratory, Pharmacy Department, Federal University of Sergipe, Sao Cristovao, SE, 49100-000, Brazil.
Special attention has been given to the mosquito Aedes aegypti Linn. (Diptera: Culicidae) owing to numerous
dengue epidemic outbreaks worldwide. Failure to control vector spreading is accounted for unorganized urban growth and
resistance to larvicides and insecticides. Therefore, researchers are currently searching for new and more efficient larvicides
and insecticides to aid dengue control measures. Triptamine is known to affect insect behavior, development, and
physiology. Expression of this compound in plants has reduced the growth rate of herbivore insects. In view of these facts,
it was of our interest to synthesize triptamine amide derivatives as potential larvicides against Ae. aegypti, establishing a
Structure-Activity Relationship. Eleven amide derivatives of triptamine were synthesized, characterized, and evaluated for
their larvicidal activity against third-instar Ae. aegypti larvae. N-(2-(1H-indol-3-yl)ethyl)-2,2,2-trichloroacetamide exhibited
the highest overall larvicidal potency, while N-(2-(1H-Indol-3-yl)ethyl) acetamide displayed the lowest larvicidal potency.
A regression equation correlating the larvicidal activity with Log P was obtained. We have found a clear relationship
between the larvicidal activity of non-chlorinated compounds and Log P. Analysis of the relationship between Log P
and larvicidal activity against Ae. aegypti may be useful in the evaluation of potential larvicidal compounds.
Keywords: QSAR, tryptamine derivatives, Aedes aegypti, larvicidal activity, dengue, neglected diseases.
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