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This work focuses on the search and development of drugs that may become new alternatives to the commercial drugs currently available for treatment of leishmaniasis. We have designed and synthesized 12 derivatives of bis(spiropyrazolone)cyclopropanes. We then characterized their potential application in therapeutic use. For this, the in vitro biological activities against three eukaryotic models-S. cerevisiae, five cancer cell lines, and the parasite L. mexicana-were evaluated. In addition, cytotoxicity against non-cancerous mammalian cells has been evaluated and other properties of interest have been characterized, such as genotoxicity, antioxidant properties and, in silico predictive adsorption, distribution, metabolism, and excretion (ADME). The results that we present here represent a first screening, indicating two derivatives of bis(spiropyrazolone)cyclopropanes as good candidates for the treatment of leishmaniasis. They have good specificity against parasites with respect to mammalian cells.
Ferrocenyl thioketones reacted with donor-acceptor cyclopropanes in dichloromethane at room temperature in the presence of catalytic amounts of Sc(OTf)3 yielding tetrahydrothiophene derivatives, products of formal [3 + 2]-cycloaddition reactions, in moderate to high yields. In all studied cases, dimethyl 2-arylcyclopropane dicarboxylates reacted with the corresponding aryl ferrocenyl thioketones in a completely diastereoselective manner to form single products in which (C-2)-Ar and (C-5)-ferrocenyl groups were oriented in a cis-fashion. In contrast, the same cyclopropanes underwent reaction with alkyl ferrocenyl thioketones to form nearly equal amounts of both diastereoisomeric tetrahydrothiophenes. A low selectivity was also observed in the reaction of a 2-phthalimide-derived cyclopropane with ferrocenyl phenyl thioketone.
The epicuticle of insects is usually coated with a complex mixture of hydrocarbons, primarily straight-chain and methyl-branched alkanes and alkenes. We were interested in whether springtails (Collembola), a sister class of the insects, also use such compounds. We focused here on Vertagopus sarekensis, an abundant Isotomidae species in European high alpine regions, exhibiting coordinated group behavior and migration. This coordination, suggesting chemical communication, made the species interesting for our study on epicuticular hydrocarbons in springtails with different degrees of group behavior. We isolated a single hydrocarbon from its surface, which is the major epicuticular lipid. The structure was deduced by NMR analysis and GC/MS including derivatization. Total synthesis confirmed the structure as cis,cis-3,4,13,14-bismethylene-24-methyldotriacontane (4, sarekensane). The GC/MS analyses of some other cyclopropane hydrocarbons also synthesized showed the close similarity of both mass spectra and gas chromatographic retention indices of alkenes and cyclopropanes. Therefore, analyses of cuticular alkenes must be performed with appropriate derivatization to distinguish these two types of cuticular hydrocarbons. Sarekensane (4) is the first nonterpenoid cuticular hydrocarbon from Collembola that is biosynthesized via the fatty acid pathway, as are insect hydrocarbons, and contains unprecedented cyclopropane rings in the chain, not previously reported from arthropods.
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