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rdf:type |
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lifeskim:mentions |
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pubmed:issue |
9
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pubmed:dateCreated |
2010-4-30
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pubmed:abstractText |
An efficient synthesis of C-1 derivatives of 7-deoxypancratistatin is reported. The key steps include the following: selective opening of an epoxide with aluminum acetylide in the presence of an aziridine; solid-state silica-gel-catalyzed opening of an aziridine; and oxidative cleavage of a phenanthrene core and its recyclization to phenanthridone to provide the key C-1 aldehyde 22. The conversion of this aldehyde to C-1 acetoxymethyl and C-1 hydroxymethyl derivatives is described along with the evaluation of their biological activity against several cancer cell lines and in an apoptosis study. The C-1 acetoxymethyl derivative has shown promising activity comparable to that of the natural product. In addition, a total synthesis of trans-dihydrolycoricidine and a formal total synthesis of 7-deoxypancratistatin are reported from aldehyde 22. Detailed experimental and spectral data are provided for all new compounds.
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pubmed:grant |
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pubmed:commentsCorrections |
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-11073675,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-11206451,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-11304174,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-11772104,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-12353988,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-12467383,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-12542352,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-1336040,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-15043403,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-15125958,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-15387596,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-15730244,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-16183280,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-16321018,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-16408886,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-17338575,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-17685535,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-18154271,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-18163635,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-18225861,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-18489166,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-19240946,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-19243131,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-19522518,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-19743883,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-2670929,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-7906395,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20373760-8277308
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pubmed:language |
eng
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pubmed:journal |
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pubmed:citationSubset |
IM
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pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/7-deoxypancratistatin,
http://linkedlifedata.com/resource/pubmed/chemical/Aldehydes,
http://linkedlifedata.com/resource/pubmed/chemical/Amaryllidaceae Alkaloids,
http://linkedlifedata.com/resource/pubmed/chemical/Antineoplastic Agents, Phytogenic,
http://linkedlifedata.com/resource/pubmed/chemical/Aziridines,
http://linkedlifedata.com/resource/pubmed/chemical/Epoxy Compounds,
http://linkedlifedata.com/resource/pubmed/chemical/Isoquinolines,
http://linkedlifedata.com/resource/pubmed/chemical/Phenanthrenes,
http://linkedlifedata.com/resource/pubmed/chemical/aziridine,
http://linkedlifedata.com/resource/pubmed/chemical/phenanthrene
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pubmed:status |
MEDLINE
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pubmed:month |
May
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pubmed:issn |
1520-6904
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pubmed:author |
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pubmed:issnType |
Electronic
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pubmed:day |
7
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pubmed:volume |
75
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
3069-84
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pubmed:dateRevised |
2011-9-26
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pubmed:meshHeading |
pubmed-meshheading:20373760-Aldehydes,
pubmed-meshheading:20373760-Amaryllidaceae Alkaloids,
pubmed-meshheading:20373760-Antineoplastic Agents, Phytogenic,
pubmed-meshheading:20373760-Apoptosis,
pubmed-meshheading:20373760-Aziridines,
pubmed-meshheading:20373760-Catalysis,
pubmed-meshheading:20373760-Cell Line, Tumor,
pubmed-meshheading:20373760-Cyclization,
pubmed-meshheading:20373760-Drug Screening Assays, Antitumor,
pubmed-meshheading:20373760-Epoxy Compounds,
pubmed-meshheading:20373760-Humans,
pubmed-meshheading:20373760-Isoquinolines,
pubmed-meshheading:20373760-Molecular Structure,
pubmed-meshheading:20373760-Oxidation-Reduction,
pubmed-meshheading:20373760-Phenanthrenes,
pubmed-meshheading:20373760-Stereoisomerism,
pubmed-meshheading:20373760-Structure-Activity Relationship
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pubmed:year |
2010
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pubmed:articleTitle |
Chemoenzymatic synthesis of Amaryllidaceae constituents and biological evaluation of their C-1 analogues. The next generation synthesis of 7-deoxypancratistatin and trans-dihydrolycoricidine.
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pubmed:affiliation |
Chemistry Department and Centre for Biotechnology, Brock University, 500 Glenridge Avenue, St. Catharines, Ontario L2S 3A1, Canada.
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't,
Research Support, N.I.H., Extramural
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