- Design, synthesis and cytotoxicity of novel 3′-N-alkoxycarbonyl docetaxel analogs
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By-product 9a exhibited potent cytotoxicity against both SK-OV-3 and A549 cell lines. The structure of 9a was characterized using 1D and 2D NMR experiments and confirmed by synthesis to afford a diastereomeric mixture (16a) that was identical to 9a, as well as a pair of diastereomers (R)-16b and (S)-16c. The preliminary SAR study demonstrated that analogs with an (R)-configuration were slightly more potent than analogs with an (S)-configuration. In addition, α,α-gem-dimethyl analogs 16g-i were the most potent analogs in this series, exhibiting similar potency to docetaxel and greater potency than Taxol against the SK-OV-3 cell line. For the A549 cell line, analogs 16g-i were more potent (>65-fold) than both docetaxel and Taxol.
- Chang, Jun,Hao, Xiao-Dong,Hao, Yun-Peng,Lu, Hong-Fu,Yu, Jian-Ming,Sun, Xun
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Read Online
- Method for preparing taxane natural product
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The invention discloses a method for preparing a taxane natural product. The taxane natural product is 10-deacetyl cephalomannine. The method includes the steps that 7,10-Di-Troc-docetaxel is dissolved in formic acid, dichloromethane is added for dilution
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Paragraph 0039-0041; 0048-0049; 0053-0054
(2019/11/20)
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- Method for purifying docetaxel
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The invention discloses a method for purifying docetaxel. A docetaxel solid precipitates from a dichloromethane and toluene mixed solution. The purifying method has the advantages of great reduction of the single content of every impurity in docetaxel, introduction of few impurities, improvement of the purity of the product, and high yield, and is very suitable for industrial large-scale production, and the obtained product meets preparation demands, and can be directly used to prepare a docetaxel injection.
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- PREPARATION OF DOCETAXEL
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The present invention relates to docetaxel and processes for preparing docetaxel, including process-related intermediates. The present invention also relates to processes for preparing substantially pure docetaxel and intermediates.
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Page/Page column 24
(2010/07/10)
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- Design, synthesis and biological evaluation of novel fluorinated docetaxel analogues
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A series of novel fluorinated docetaxel analogues have been synthesized and evaluated in vitro and in vivo. Incorporated one, two or three fluorine atom(s) either at both meta position on C-2 benzolate and 3′-N-tert-butyloxyl group or only at 3′-N-tert-butyloxyl group has resulted in potent analogues which have comparable or superior in vitro and in vivo cytotoxicity to docetaxel. Among them, compounds 14d and 14e have displayed more potent cytotoxicity than docetaxel both in human cancer cell line SK-OV-3 in vitro and in human non-small cell lung cancer A549 xenografts in vivo. Preliminary data show that compound 14a has reduced acute animal toxicity in mice compared with docetaxel.
- Lu, Hong-Fu,Sun, Xun,Xu, Liang,Lou, Li-Guang,Lin, Guo-Qiang
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experimental part
p. 482 - 491
(2009/09/06)
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- Improved protection and esterification of a precursor of the taxotere and taxol side chains
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(4S,5R)-N-BOC-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylic acid 8 was prepared and efficiently esterified by conveniently protected baccatins 9a,b. Smooth deprotection in formic acid gave the N-deprotected intermediates of Taxotere and taxol. This protocol did not generate any epimerization at C-2′ and constitutes a pratical method to prepare Taxotere, taxol and analogs.
- Commercon,Bezard,Bernard,Bourzat
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p. 5185 - 5188
(2007/10/02)
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