461462-86-2Relevant academic research and scientific papers
Orally active, water-soluble antimalarial 3-aryltrioxanes: Short synthesis and preclinical efficacy testing in rodents
Posner, Gary H.,Jeon, Heung Bae,Ploypradith, Poonsakdi,Paik, Ik-Hyeon,Borstnik, Kristina,Xie, Suji,Shapiro, Theresa A.
, p. 3824 - 3828 (2002)
Short chemical syntheses of four new antimalarial trioxanes are presented, starting with inexpensive and commercially available cyclohexanone. Almost exclusive formation of the trioxane 12α-stereoisomers simplifies product purification. Carboxyphenyltrioxanes 3 and 5 are thermally stable in air even at 60°C for 24 h. When administered orally, these new carboxyphenyltrioxanes are highly efficacious in curing malaria-infected mice. Important for their practical in vivo administration, these new synthetic antimalarial trioxanes 3 and 5 are 14-20 times more soluble in water at pH 7.4 than is artelinic acid (1), a leading semisynthetic, herb-derived antimalarial trioxane drug candidate.
