The comparative antimalarial properties of weak base and neutral synthetic ozonides
Thirty-three N-acyl 1,2,4-dispiro trioxolanes (secondary ozonides) were synthesized. For these ozonides, weak base functional groups were not required for high antimalarial potency against Plasmodium falciparum in vitro, but were necessary for high antimalarial efficacy in Plasmodium berghei-infecte...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2010-01, Vol.20 (2), p.563-566 |
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| creator | Tang, Yuanqing Wittlin, Sergio Charman, Susan A. Chollet, Jacques Chiu, Francis C.K. Morizzi, Julia Johnson, Lisa M. Tomas, Josefina Santo Scheurer, Christian Snyder, Chistopher Zhou, Lin Dong, Yuxiang Charman, William N. Matile, Hugues Urwyler, Heinrich Dorn, Arnulf Vennerstrom, Jonathan L. |
| description | Thirty-three
N-acyl 1,2,4-dispiro trioxolanes (secondary ozonides) were synthesized. For these ozonides, weak base functional groups were not required for high antimalarial potency against
Plasmodium falciparum in vitro, but were necessary for high antimalarial efficacy in
Plasmodium berghei-infected mice. A wide range of Log
P/
D
pH
7.4 values were tolerated, although more lipophilic ozonides tended to be less metabolically stable. |
| doi_str_mv | 10.1016/j.bmcl.2009.11.088 |
| format | Article |
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N-acyl 1,2,4-dispiro trioxolanes (secondary ozonides) were synthesized. For these ozonides, weak base functional groups were not required for high antimalarial potency against
Plasmodium falciparum in vitro, but were necessary for high antimalarial efficacy in
Plasmodium berghei-infected mice. A wide range of Log
P/
D
pH
7.4 values were tolerated, although more lipophilic ozonides tended to be less metabolically stable.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2009.11.088</identifier><identifier>PMID: 19962893</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>1,2,4-Trioxolanes ; Animals ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antimalarial ; Antimalarials - chemical synthesis ; Antimalarials - chemistry ; Antimalarials - pharmacokinetics ; Antiparasitic agents ; Artemisinin ; Biological and medical sciences ; Heterocyclic Compounds - chemical synthesis ; Heterocyclic Compounds - chemistry ; Heterocyclic Compounds - pharmacokinetics ; Medical sciences ; Mice ; Peroxides ; Pharmacology. Drug treatments ; Plasmodium falciparum ; Plasmodium falciparum - drug effects ; Rats ; Secondary ozonides</subject><ispartof>Bioorganic & medicinal chemistry letters, 2010-01, Vol.20 (2), p.563-566</ispartof><rights>2009 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright 2009 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c416t-4d6ede5ef33e2e6837f265123e470ae29b749dbf18d3b90501b1c674a7e462ab3</citedby><cites>FETCH-LOGICAL-c416t-4d6ede5ef33e2e6837f265123e470ae29b749dbf18d3b90501b1c674a7e462ab3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2009.11.088$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,777,781,3537,27905,27906,45976</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22389471$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19962893$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tang, Yuanqing</creatorcontrib><creatorcontrib>Wittlin, Sergio</creatorcontrib><creatorcontrib>Charman, Susan A.</creatorcontrib><creatorcontrib>Chollet, Jacques</creatorcontrib><creatorcontrib>Chiu, Francis C.K.</creatorcontrib><creatorcontrib>Morizzi, Julia</creatorcontrib><creatorcontrib>Johnson, Lisa M.</creatorcontrib><creatorcontrib>Tomas, Josefina Santo</creatorcontrib><creatorcontrib>Scheurer, Christian</creatorcontrib><creatorcontrib>Snyder, Chistopher</creatorcontrib><creatorcontrib>Zhou, Lin</creatorcontrib><creatorcontrib>Dong, Yuxiang</creatorcontrib><creatorcontrib>Charman, William N.</creatorcontrib><creatorcontrib>Matile, Hugues</creatorcontrib><creatorcontrib>Urwyler, Heinrich</creatorcontrib><creatorcontrib>Dorn, Arnulf</creatorcontrib><creatorcontrib>Vennerstrom, Jonathan L.</creatorcontrib><title>The comparative antimalarial properties of weak base and neutral synthetic ozonides</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Thirty-three
N-acyl 1,2,4-dispiro trioxolanes (secondary ozonides) were synthesized. For these ozonides, weak base functional groups were not required for high antimalarial potency against
Plasmodium falciparum in vitro, but were necessary for high antimalarial efficacy in
Plasmodium berghei-infected mice. A wide range of Log
P/
D
pH
7.4 values were tolerated, although more lipophilic ozonides tended to be less metabolically stable.</description><subject>1,2,4-Trioxolanes</subject><subject>Animals</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antimalarial</subject><subject>Antimalarials - chemical synthesis</subject><subject>Antimalarials - chemistry</subject><subject>Antimalarials - pharmacokinetics</subject><subject>Antiparasitic agents</subject><subject>Artemisinin</subject><subject>Biological and medical sciences</subject><subject>Heterocyclic Compounds - chemical synthesis</subject><subject>Heterocyclic Compounds - chemistry</subject><subject>Heterocyclic Compounds - pharmacokinetics</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Peroxides</subject><subject>Pharmacology. Drug treatments</subject><subject>Plasmodium falciparum</subject><subject>Plasmodium falciparum - drug effects</subject><subject>Rats</subject><subject>Secondary ozonides</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp90M9rFTEQwPEgFvta_Qc8yF60p10zSTbZgJdSWi0UPFjBW8gmszTP_fFM8ir1rzfLe-itp7l8Zhi-hLwF2gAF-XHb9JMbG0apbgAa2nUvyAaEFDUXtH1JNlRLWnda_DglZyltKQVBhXhFTkFryTrNN-Tb_QNWbpl2NtocHrGycw6THW0Mdqx2cdlhzAFTtQzVb7Q_q96mFflqxn2OxaSnOT9gDq5a_ixz8Jhek5PBjgnfHOc5-X5zfX_1pb77-vn26vKudgJkroWX6LHFgXNkKDuuBiZbYByFohaZ7pXQvh-g87zXtKXQg5NKWIVCMtvzc3JxuFve_LXHlM0UksNxtDMu-2QU551ulZRFfnhWMhCilWqF7ABdXFKKOJhdLDnikwFq1uhma9boZo1uAEyJXpbeHa_v-wn9_5Vj5QLeH4FNzo5DtLML6Z9jrPwpFBT36eCwVHsMGE1yAWeHPkR02fglPPfHXxttoJc</recordid><startdate>20100115</startdate><enddate>20100115</enddate><creator>Tang, Yuanqing</creator><creator>Wittlin, Sergio</creator><creator>Charman, Susan A.</creator><creator>Chollet, Jacques</creator><creator>Chiu, Francis C.K.</creator><creator>Morizzi, Julia</creator><creator>Johnson, Lisa M.</creator><creator>Tomas, Josefina Santo</creator><creator>Scheurer, Christian</creator><creator>Snyder, Chistopher</creator><creator>Zhou, Lin</creator><creator>Dong, Yuxiang</creator><creator>Charman, William N.</creator><creator>Matile, Hugues</creator><creator>Urwyler, Heinrich</creator><creator>Dorn, Arnulf</creator><creator>Vennerstrom, Jonathan L.</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20100115</creationdate><title>The comparative antimalarial properties of weak base and neutral synthetic ozonides</title><author>Tang, Yuanqing ; Wittlin, Sergio ; Charman, Susan A. ; Chollet, Jacques ; Chiu, Francis C.K. ; Morizzi, Julia ; Johnson, Lisa M. ; Tomas, Josefina Santo ; Scheurer, Christian ; Snyder, Chistopher ; Zhou, Lin ; Dong, Yuxiang ; Charman, William N. ; Matile, Hugues ; Urwyler, Heinrich ; Dorn, Arnulf ; Vennerstrom, Jonathan L.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c416t-4d6ede5ef33e2e6837f265123e470ae29b749dbf18d3b90501b1c674a7e462ab3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>1,2,4-Trioxolanes</topic><topic>Animals</topic><topic>Antibiotics. 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N-acyl 1,2,4-dispiro trioxolanes (secondary ozonides) were synthesized. For these ozonides, weak base functional groups were not required for high antimalarial potency against
Plasmodium falciparum in vitro, but were necessary for high antimalarial efficacy in
Plasmodium berghei-infected mice. A wide range of Log
P/
D
pH
7.4 values were tolerated, although more lipophilic ozonides tended to be less metabolically stable.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>19962893</pmid><doi>10.1016/j.bmcl.2009.11.088</doi><tpages>4</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry letters, 2010-01, Vol.20 (2), p.563-566 |
| issn | 0960-894X 1464-3405 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | 1,2,4-Trioxolanes Animals Antibiotics. Antiinfectious agents. Antiparasitic agents Antimalarial Antimalarials - chemical synthesis Antimalarials - chemistry Antimalarials - pharmacokinetics Antiparasitic agents Artemisinin Biological and medical sciences Heterocyclic Compounds - chemical synthesis Heterocyclic Compounds - chemistry Heterocyclic Compounds - pharmacokinetics Medical sciences Mice Peroxides Pharmacology. Drug treatments Plasmodium falciparum Plasmodium falciparum - drug effects Rats Secondary ozonides |
| title | The comparative antimalarial properties of weak base and neutral synthetic ozonides |
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