| Hemi-synthesis and biological activity of new analogues of podophyllotoxin. | |
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MedLine Citation:
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PMID: 12213460 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Various 4-analogues of podophyllotoxin and epipodophyllotoxin were obtained via the formation of the corresponding 4-keto derivatives. Methyloximation of podophyllotoxone, followed by subsequent catalytic hydrogenation, gave stereoselective access to 4-alpha-amino-4-deoxypodophyllotoxin and from there, to the corresponding acetamido and formamido derivatives. Base-catalyzed isomerisation of 4-alpha-amino-4-deoxypodophyllotoxin led to the corresponding picropodophyllin isomer while the 4-beta-amino afforded a neopodophyllotoxin-like derivative. On the other hand, oxirane and hydroxymethyl-containing analogues were prepared from podophyllotoxin and 4-epi-4'-demethyl-podophyllotoxin, using a Takai olefination strategy. In the latter series, carboxaldehyde- and carboxylic acid-containing derivatives were also synthesized. |
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Authors:
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Emmanuel Roulland; Prokopios Magiatis; Paola Arimondo; Emmanuel Bertounesque; Claude Monneret |
Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Bioorganic & medicinal chemistry Volume: 10 ISSN: 0968-0896 ISO Abbreviation: Bioorg. Med. Chem. Publication Date: 2002 Nov |
Date Detail:
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Created Date: 2002-09-05 Completed Date: 2003-03-04 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 9413298 Medline TA: Bioorg Med Chem Country: England |
Other Details:
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Languages: eng Pagination: 3463-71 Citation Subset: IM |
Affiliation:
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Laboratoire de Pharmacochimie, UMR 176 CNRS-IC, Section Recherche de l'Institut Curie, 26 rue d'Ulm, Paris, France. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Angiogenesis Inhibitors
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chemical synthesis,
pharmacology Animals Antineoplastic Agents, Phytogenic / chemical synthesis*, pharmacology* Apoptosis / drug effects Cell Cycle / drug effects DNA Topoisomerases, Type I / antagonists & inhibitors Enzyme Inhibitors / chemical synthesis, pharmacology Humans Leukemia L1210 / drug therapy Necrosis Podophyllotoxin / analogs & derivatives*, chemical synthesis*, pharmacology Stereoisomerism Structure-Activity Relationship Swine Tubulin / drug effects, metabolism |
| Chemical | |
Reg. No./Substance:
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0/Angiogenesis Inhibitors; 0/Antineoplastic Agents, Phytogenic; 0/Enzyme Inhibitors; 0/Tubulin; 518-28-5/Podophyllotoxin; EC 5.99.1.2/DNA Topoisomerases, Type I |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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