Novel 5beta-hydroxyspirostan-6-ones ecdysteroid antagonists: synthesis and biological testing.
Eight new 5beta-hydroxy-spirostan-6-ones bearing hydroxy and amino functions in the A ring, i.e., 3beta-OH, 3alpha-OH, 2beta,3beta-OH, 2alpha,3beta-OH, 3beta-NH2, 2alpha-NH2-3beta-OH, 2beta-NH2-3beta-OH, and 2beta-OH-3beta-NH2, were efficiently synthesized, and their antiecdysteroid activities were evaluated on the metamorphosis bioassay of mosquito Aedes aegypti. To our knowledge, these new steroids represent the first 5beta-hydroxy-spirostanes which have been tested for antiecdysteroid activity in mosquitoes. The higher antagonistic effect was found for compounds bearing the 3beta-hydroxy and 2beta,3beta-dihydroxy functionality, which show promise as environmental friendly insecticides.
Rivera
Daniel G
DG
Center for Natural Products Studies, Faculty of Chemistry, University of Havana, Zapata y G, Vedado 10400, Ciudad Habana, Cuba. drivera@ipb-halle.de
León
Fredy
F
Coll
Francisco
F
Davison
Gema P
GP
D000330:Aedes / Q000187:drug effects*; D000818:Animals; D026461:Ecdysteroids / Q000037:antagonists & inhibitors*; D007306:Insecticides / Q000138:chemical synthesis* / Q000494:pharmacology; D008675:Metamorphosis, Biological / Q000187:drug effects; D008968:Molecular Conformation; D015394:Molecular Structure; D013150:Spirostans / Q000138:chemical synthesis* / Q000737:chemistry*; D013329:Structure-Activity Relationship
D026461:Ecdysteroids; D007306:Insecticides; D013150:Spirostans