Source:http://linkedlifedata.com/resource/pubmed/id/11448231
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Predicate | Object |
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
15
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pubmed:dateCreated |
2001-7-12
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pubmed:abstractText |
A regio- and stereospecific synthesis of monoarylimino o-quinones derived from beta-lapachone (1) was achieved by treatment of the quinone with a slight excess of an arylamine in the presence of an excess of triethylamine/titanium tetrachloride 4:1. Imine formation occurred exclusively at position 6, giving the Z diastereomer, as determined by single-crystal X-ray analysis. In vitro tests for cytotoxicity in 55 human cancer cell cultures showed a substantial loss in activity for the p-nitrophenylimine (5), whereas the phenylimine (2), p-methylphenylimine (3), and p-methoxyphenylimine (4) retained (or bettered) most of the cytotoxicity and selectivity of the parent quinone. Preliminary in vivo testing in hollow fiber assays against a standard panel of 12 human tumor cell lines showed that although beta-lapachone failed, compounds 2 and 3 had good scores with net cell kills.
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pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/Antineoplastic Agents,
http://linkedlifedata.com/resource/pubmed/chemical/Imines,
http://linkedlifedata.com/resource/pubmed/chemical/Naphthalenes,
http://linkedlifedata.com/resource/pubmed/chemical/Naphthoquinones,
http://linkedlifedata.com/resource/pubmed/chemical/Pyrans,
http://linkedlifedata.com/resource/pubmed/chemical/beta-lapachone
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pubmed:status |
MEDLINE
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pubmed:month |
Jul
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pubmed:issn |
0022-2623
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:day |
19
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pubmed:volume |
44
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
2486-9
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pubmed:dateRevised |
2006-11-15
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pubmed:meshHeading |
pubmed-meshheading:11448231-Antineoplastic Agents,
pubmed-meshheading:11448231-Crystallography, X-Ray,
pubmed-meshheading:11448231-Drug Screening Assays, Antitumor,
pubmed-meshheading:11448231-Humans,
pubmed-meshheading:11448231-Imines,
pubmed-meshheading:11448231-Magnetic Resonance Spectroscopy,
pubmed-meshheading:11448231-Naphthalenes,
pubmed-meshheading:11448231-Naphthoquinones,
pubmed-meshheading:11448231-Pyrans,
pubmed-meshheading:11448231-Stereoisomerism,
pubmed-meshheading:11448231-Structure-Activity Relationship,
pubmed-meshheading:11448231-Tumor Cells, Cultured
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pubmed:year |
2001
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pubmed:articleTitle |
Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of beta-lapachone.
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pubmed:affiliation |
Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, (1428) Buenos Aires, Argentina.
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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