Enantioselective synthesis and anti-parasitic properties of aporphine natural products
| Autor: | Maiara Amaral, Eliza McHugh, Andre G. Tempone, Edward A. Anderson, Pauline Pieper |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
Chagas disease
biology 010405 organic chemistry Chemistry Organic Chemistry Enantioselective synthesis 010402 general chemistry medicine.disease biology.organism_classification 01 natural sciences Biochemistry Antiparasitic agent Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound Visceral leishmaniasis Dicentrine Drug Discovery medicine Aporphine Leishmania infantum Trypanosoma cruzi |
| Zdroj: | Tetrahedron. 76:130814 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2019.130814 |
| Popis: | Chagas disease and visceral leishmaniasis are neglected protozoan diseases with significant impact in developing countries. Due to the limited number and toxicity of current therapies, new drug leads are urgently needed. In this work, four aporphine natural products were synthesized using an enantioselective, modular and convergent strategy, comprising eight steps in the longest linear sequence; key steps included Bischler-Napieralski cyclization/Noyori asymmetric reduction to construct the tetrahydroisoquinolines, and palladium-catalyzed arylation to close the C ring. Norglaucine, nordicentrine and dicentrine showed promising bioactivity against T. cruzi and L. infantum, suggesting potential for further development of these scaffolds as antiparasitic agents. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect