Synthesis and repellent efficacy of a new chiral piperidine analog: comparison with Deet and Bayrepel activity in human-volunteer laboratory assays against Aedes aegypti and Anopheles stephensi
Autor(es): Klun Jerome A,Khrimian Ashot,Margaryan Armenak,Kramer Matthew,Debboun Mustapha
Resumo: Optically active (1S,2'S)-2-methylpiperidinyl-3-cyclohexen-1-carboxamide (SS220) is a new synthetic arthropod repellent. A three-step synthesis based on a chiral Diels-Alder reaction and diastereomeric resolution of 2-methylpiperidine was developed to prepare the compound. Quantitative laboratory assays using human volunteers compared the effectiveness of SS220 with the commonly used repellents Deet and Bayrepel against Aedes aegypti (Linnaeus) and Anopheles stephensi Liston mosquitoes. In two experiments using Aedes aegypti, one using a single identical dose and one with varying doses used to develop a dose-response curve, SS220 was as effective as Deet and both compounds were more effective than Bayrepel. The three compounds were equally effective against An. stephensi. Based on the ease of its synthetic preparation and its repellent efficacy, we surmise that SS220 is a candidate to serve as a new and effective alternate repellent for protection against arthropod disease vectors.
Palavras-Chave: (1S, 2 S)-2-methylpiperidinyl-3-cyclohexen-1-carboxamide; 2-(2-hydroxyethyl)-1-piperidinecarboxylic acid 1-methylpropyl ester; N; N-diethyl-3-methylbenzamide; Aedes aegypti; Anopheles stephensi
Imprenta: Journal of Medical Entomology, v. 40, n. 3, p. 293-299, 2003
Identificador do objeto digital: 10.3390/molecules18033564
Descritores: Aedes aegypti - Repellent
Data de publicação: 2003
