Synthesis and Potent Antimalarial Activity of Kalihinol B
Of the 50+ kalihinane diterpenoids reported to date, only five had been tested for antimalarial activity, in spite of the fact that kalihinol A is the most potent among the members of the larger family of antimalarial isocyanoterpenes. We have validated a strategy designed to access many of the kali...
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| Veröffentlicht in: | Journal of the American Chemical Society Jg. 137; H. 15; S. 4912 - 4915 |
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| Abstract | Of the 50+ kalihinane diterpenoids reported to date, only five had been tested for antimalarial activity, in spite of the fact that kalihinol A is the most potent among the members of the larger family of antimalarial isocyanoterpenes. We have validated a strategy designed to access many of the kalihinanes with a 12-step enantioselective synthesis of kalihinol B, the tetrahydrofuran isomer of kalihinol A (a tetrahydropyran). Kalihinol B shows similarly high potency against chloroquine-resistant Plasmodium falciparum. |
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| AbstractList | Of the 50+ kalihinane diterpenoids reported to date, only five had been tested for antimalarial activity, in spite of the fact that kalihinol A is the most potent among the members of the larger family of antimalarial isocyanoterpenes. We have validated a strategy designed to access many of the kalihinanes with a 12-step enantioselective synthesis of kalihinol B, the tetrahydrofuran isomer of kalihinol A (a tetrahydropyran). Kalihinol B shows similarly high potency against chloroquine-resistant Plasmodium falciparum. Of the 50+ kalihinane diterpenoids reported to date, only five had been tested for antimalarial activity, in spite of the fact that kalihinol A is the most potent among the members of the larger family of antimalarial isocyanoterpenes. We have validated a strategy designed to access many of the kalihinanes with a 12-step enantioselective synthesis of kalihinol B, the tetrahydrofuran isomer of kalihinol A (a tetrahydropyran). Kalihinol B shows similarly high potency against chloroquine-resistant Plasmodium falciparum.Of the 50+ kalihinane diterpenoids reported to date, only five had been tested for antimalarial activity, in spite of the fact that kalihinol A is the most potent among the members of the larger family of antimalarial isocyanoterpenes. We have validated a strategy designed to access many of the kalihinanes with a 12-step enantioselective synthesis of kalihinol B, the tetrahydrofuran isomer of kalihinol A (a tetrahydropyran). Kalihinol B shows similarly high potency against chloroquine-resistant Plasmodium falciparum. |
| Author | Prudhomme, Jacques Daub, Mary Elisabeth Le Roch, Karine Vanderwal, Christopher D |
| AuthorAffiliation | Department of Chemistry Department of Cell Biology and Neuroscience University of California, Irvine University of California, Riverside |
| AuthorAffiliation_xml | – name: Department of Chemistry – name: University of California, Riverside – name: University of California, Irvine – name: Department of Cell Biology and Neuroscience |
| Author_xml | – sequence: 1 givenname: Mary Elisabeth surname: Daub fullname: Daub, Mary Elisabeth – sequence: 2 givenname: Jacques surname: Prudhomme fullname: Prudhomme, Jacques – sequence: 3 givenname: Karine surname: Le Roch fullname: Le Roch, Karine – sequence: 4 givenname: Christopher D surname: Vanderwal fullname: Vanderwal, Christopher D email: cdv@uci.edu |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/25815413$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.1021/ja802730a 10.1016/j.tet.2012.01.084 10.1016/j.tet.2010.02.088 10.1002/chem.201104029 10.1021/jo0522862 10.1371/journal.pone.0002335 10.1021/jo026837p 10.1039/c4np00109e 10.1021/ja310129b 10.1021/ol049918b 10.1016/j.tet.2003.08.082 10.1038/nature12472 10.1021/ol0517729 10.1021/ol2027587 10.1056/NEJMoa1314981 10.1039/c1cc16468f 10.1021/ol301874x |
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| Snippet | Of the 50+ kalihinane diterpenoids reported to date, only five had been tested for antimalarial activity, in spite of the fact that kalihinol A is the most... |
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| SubjectTerms | Antimalarials - chemical synthesis Antimalarials - chemistry Antimalarials - pharmacology Chemistry Chemistry, Multidisciplinary Chloroquine - pharmacology Diterpenes - chemical synthesis Diterpenes - chemistry Diterpenes - pharmacology Drug Resistance - drug effects Molecular Structure Parasitic Sensitivity Tests Physical Sciences Plasmodium falciparum - drug effects Science & Technology |
| Title | Synthesis and Potent Antimalarial Activity of Kalihinol B |
| URI | http://dx.doi.org/10.1021/jacs.5b01152 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000353606700010 https://www.ncbi.nlm.nih.gov/pubmed/25815413 https://www.proquest.com/docview/1675169371 |
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