Semisynthesis of D-Ring Modified Taxoids:  Novel Thia Derivatives of Docetaxel

Two novel 5(20)-thia analogues of docetaxel have been synthesized from 10-deacetylbaccatin III or taxine B and isotaxine B. The key step of these syntheses is the concomitant thietane ring formation and acetylation of the tertiary alcohol at C-4. Both compounds are less cytotoxic than docetaxel but...

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Published inJournal of organic chemistry Vol. 66; no. 15; pp. 5058 - 5065
Main Authors Mercklé, Ludovic, Dubois, Joëlle, Place, Estelle, Thoret, Sylviane, Guéritte, Françoise, Guénard, Daniel, Poupat, Christiane, Ahond, Alain, Potier, Pierre
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 27.07.2001
Amer Chemical Soc
Subjects
Antineoplastic Agents, Phytogenic - chemical synthesis
Antineoplastic Agents, Phytogenic - pharmacology
Chemistry
Chemistry, Organic
Docetaxel
Humans
Indicators and Reagents
KB Cells
Microtubules - drug effects
Paclitaxel - analogs & derivatives
Paclitaxel - chemical synthesis
Paclitaxel - pharmacology
Physical Sciences
Plant Leaves - chemistry
Plants, Medicinal - chemistry
Science & Technology
Taxoids
ANALOGS
INVITRO
III DERIVATIVES
BIOLOGICAL EVALUATION
TAXANES
TUBULIN
ALKALOIDS
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Summary:Two novel 5(20)-thia analogues of docetaxel have been synthesized from 10-deacetylbaccatin III or taxine B and isotaxine B. The key step of these syntheses is the concomitant thietane ring formation and acetylation of the tertiary alcohol at C-4. Both compounds are less cytotoxic than docetaxel but have divergent activity on microtubule disassembly.
Bibliography:ark:/67375/TPS-SJXVBSW1-S
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ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo015539+