Synthesis of Bioactive 2-Aza-Analogues of Ipecac and Alangium Alkaloids
License to kill: Substitution of the methine carbon C2 in the ipecac or alangium alkaloids by nitrogen yields functional mimetics with low micromolar to high naonomolar IC50 values against Trypanosoma brucei, the parasite that causes African trypanosomiasis. 2‐Azaemetine shows an improved selectivit...
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| Veröffentlicht in: | ChemMedChem 2010-09, Vol.5 (9), p.1456-1464 |
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| container_title | ChemMedChem |
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| creator | Kölzer, Michael Weitzel, Kerstin Göringer, H. Ulrich Thines, Eckhard Opatz, Till |
| description | License to kill: Substitution of the methine carbon C2 in the ipecac or alangium alkaloids by nitrogen yields functional mimetics with low micromolar to high naonomolar IC50 values against Trypanosoma brucei, the parasite that causes African trypanosomiasis. 2‐Azaemetine shows an improved selectivity ratio between its antiparasitic activity and its cytotoxicity against mammalian cells compared to the parent compound. The chosen isomorphous replacement permits a modular synthesis and facilitates the combinatorial variation of the products. |
| doi_str_mv | 10.1002/cmdc.201000230 |
| format | Article |
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The chosen isomorphous replacement permits a modular synthesis and facilitates the combinatorial variation of the products.</description><subject>Alangiaceae - chemistry</subject><subject>alkaloids</subject><subject>Alkaloids - chemical synthesis</subject><subject>Alkaloids - chemistry</subject><subject>Alkaloids - toxicity</subject><subject>Aza Compounds - chemical synthesis</subject><subject>Aza Compounds - chemistry</subject><subject>Aza Compounds - toxicity</subject><subject>aza-analogues</subject><subject>cyclization</subject><subject>Ipecac - chemistry</subject><subject>natural products</subject><subject>Structure-Activity Relationship</subject><subject>Trypanocidal Agents - chemical synthesis</subject><subject>Trypanocidal Agents - chemistry</subject><subject>Trypanocidal Agents - toxicity</subject><subject>Trypanosoma brucei brucei - drug effects</subject><subject>trypanosomes</subject><issn>1860-7179</issn><issn>1860-7187</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkM9PwjAYhhujEUSvHs1unob9sa7bcaIiCWoiGI9N133DysZwHSr-9RbBxZunvkmf98mXF6FTgvsEY3qhy0z3KXYZU4b3UJdEIfYFicR-m0XcQUfWvmIcBBGJDlGHYi44CXAXDSfrRfMC1livyr1LUyndmHfwqJ98KT9ZqKKareDnc7QErbSnFpmXFGoxM6vShbkjTGaP0UGuCgsnu7eHnm6up4Nbf_wwHA2Ssa9ZRLFPqFZxTjkLUp0rzrSKApZxYAqAqDQPNeeaxKkACHKWhSTmwEORAiFBTkjGeuh8613W1Zs7rJGlsRoKdxBUKysFZ3EcMhw7sr8ldV1ZW0Mul7UpVb2WBMvNdnKznWy3c4WznXqVlpC1-O9YDoi3wIcpYP2PTg7urgZ_5f62a2wDn21X1XMZCia4fL4fyillZEIfnY99A3G9iQo</recordid><startdate>20100903</startdate><enddate>20100903</enddate><creator>Kölzer, Michael</creator><creator>Weitzel, Kerstin</creator><creator>Göringer, H. 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| language | eng |
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| source | MEDLINE; Wiley Journals |
| subjects | Alangiaceae - chemistry alkaloids Alkaloids - chemical synthesis Alkaloids - chemistry Alkaloids - toxicity Aza Compounds - chemical synthesis Aza Compounds - chemistry Aza Compounds - toxicity aza-analogues cyclization Ipecac - chemistry natural products Structure-Activity Relationship Trypanocidal Agents - chemical synthesis Trypanocidal Agents - chemistry Trypanocidal Agents - toxicity Trypanosoma brucei brucei - drug effects trypanosomes |
| title | Synthesis of Bioactive 2-Aza-Analogues of Ipecac and Alangium Alkaloids |
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