The schistosomicidal activities of seven 2-(alkylamino)-1-phenyl-1-ethanethiosulfuric acids (1a-g) (R=propyl, isopropyl, butyl, isobutyl, t-butyl, sec-butyl, cyclohexyl, respectively) were determined in female Swiss mice infected with Schistosoma mansoni. The compounds were administered in a single oral dose of 800 mg/kg to groups of 15 mice infected with 50 cercariae each. All the compounds were found to be active, a high animal mortality being observed with 1e. These compounds have a high specificity against female worms (64-100% reduction vs. 33-61% reduction in male worms). The test was repeated, a 400-mg/kg sub-dose of 1f also being tested, and similar results were observed. A 94% reduction in the number of female worms was observed when compound 1c was administered in a single 800-mg/kg dose to animals infected with 80 cercariae. Finally, the test was repeated with single 800 mg/kg oral doses of compounds 1e (highly purified) and 1f and a 400-mg/kg sub-dose of 1c. The toxicity of 1e was confirmed, while the animals that received 1c and 1f presented reductions in the worm loads corresponding to 45.9% (male worms) and 84.8% (female worms) for 1c and 50.4% (male worms) and 94.2% (female worms) for 1f.

The total synthesis of seven here-to-fore unreported aromatic aminoalkanethiosulfuric acids, their physical properties and those of the aminoalcohol and bromoalkanamine intermediates are reported. All structures were established by including 1 H and 13 C NMR, IR and MS spectroscopy and elemental analysis.

Na obtenção de ácidos N-alquilaminoalcanotiossulfúricos, existe a possibilidade de formação de dois produtos na última etapa da síntese. No caso dos sete ácidos sintetizados neste laboratório a partir de óxido de estireno e aminas primárias alifáticas, os métodos comuns de espectroscopia não foram adequados para distinguir qual dos dois isômeros foi formado. Cálculos de deslocamentos químicos de carbono-13 empregando o programa ACD/CNMR ajudaram, mas não foram conclusivos para a identificação dos produtos. O uso de técnicas como HMQC, HMBC e TOCSY permitiu a identificação dos produtos como os ácidos 2-(N-alquilamino)-1-phenyl-1-etanotiossulfúricos.In the synthesis of N-alkylaminoalkanethiosulfuric acids, there exists the possibility of forming two products in the last step of the synthesis. In the case of the seven acids synthesized in this laboratory from styrene oxide and primary aliphatic amines, the common spectroscopic methods were inadequate for distinguishing which of the two isomers was obtained. Carbon-13 chemical shift calculations employing the ACD/CNMR program were helpful, but not conclusive for identifying the products. The use of HMQC, HMBC and TOCSY techniques permitted the identification of the products as the 2-(N-alkylamino)-1-phenyl-1-ethanethiosulfuric acids.