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Medicinal Chemistry
ISSN (Print): 1573-4064
ISSN (Online): 1875-6638
VOLUME: 10
ISSUE: 6
DOI: 10.2174/1573406409666131202144010      Price:  $58









Synthesis, Activity, and QSAR Studies of Tryptamine Derivatives on Third-instar Larvae of Aedes Aegypti Linn

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Author(s): 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
Pages 580-587 (8)
Abstract:
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.
Graphical Abstract:
Keywords:
QSAR, tryptamine derivatives, Aedes aegypti, larvicidal activity, dengue, neglected diseases.
Affiliation:
Medicinal Chemistry Laboratory, Pharmacy Department, Federal University of Sergipe, Sao Cristovao, SE, 49100-000, Brazil.