- Syntheses and biological evaluation of C-30-N-acyl modified taxane analogues from 1-deoxybaccatin-VI
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A series of side-chain modified taxane analogues were synthesized and their in vitro anticancer activities against four human cancer cell lines: MDA-MB-231 (human breast cancer), PC-3 (human prostatic cancer), HepG2 and H460 (human hepatoma) were studied.
- Li, Qing-Feng,Lin, Hai-Xia,Cui, Yong-Mei,Xu, Pei-Pei
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Read Online
- A four-membered ring taxol alkane side chain compound preparation method
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The invention relates to a preparation method of a four-membered ring taxane side chain compound, and belongs to the field of synthesis of medicines. The four-membered ring taxane side chain compound as shown in the formula I is prepared from a compound as shown in the formula II. The preparation method overcomes the defects of being low in reaction yield and complicated in postprocessing, and needing column chromatography to obtain a purified product in the industrial production in the prior art, and has the advantages of simple equipment, easiness in operation, higher yield, and easiness in industrial production.
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Page/Page column 4-8
(2017/11/16)
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- A chiral four membered ring taxol alkane side chain compound preparation method
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The invention relates to a preparation method of a chiral four-membered-ring taxane side chain compound and belongs to the field of pharmaceutical synthesis. The chiral four-membered-ring taxane side chain compound as shown in the formula I is prepared from a compound as shown in the formula II through a cyclization reaction. The method overcomes the defects of the relatively high cost of (2R,3S)-phenyl isoserine methyl ester in the prior art, and has the advantages of low cost of the used achiral material, simple equipment, easiness in operation, higher yield, and easiness in industrial production.
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Paragraph 0029-0032
(2017/09/02)
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- Total synthesis of a library of designed hybrids of the microtubule-stabilising anticancer agents taxol, discodermolide and dictyostatin
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A hybrid library of the marine natural products dictyostatin and discodermolide, incorporating the taxol or taxotere side chains, were synthesised; preliminary biological evaluation in the PANC-1 cancer cell line revealed significant antiproliferative activity, demonstrating that a macrolide scaffold is an effective surrogate for the baccatin core of taxol.
- Paterson, Ian,Naylor, Guy J.,Fujita, Takeshi,Guzman, Esther,Wright, Amy E.
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supporting information; experimental part
p. 261 - 263
(2010/05/01)
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- Semisynthesis of flexible 5,7-dideoxypaclitaxel derivatives from Taxine B
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Two new 5,7-dideoxypaclitaxel derivatives with flexible C-rings have been prepared starting from Taxine B, an alkaloid isolated from the leaves of Taxus baccata. Both derivatives lack the oxetane ring present in the antitumor agent paclitaxel, but possess an oxygenated 4β-substituent as a substitute for the oxetane ring oxygen atom. These derivatives provide additional information about the importance of this oxygen atom for cytotoxic activity.
- Beusker, Patrick H.,Veldhuis, Harald,Van Den Bossche, Bianca A. C.,Scheeren, Hans W.
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p. 1761 - 1768
(2007/10/03)
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- A convenient synthesis of the paclitaxel side-chain via a diastereoselective Staudinger reaction
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The N-benzylidene dexivative of (S)-(-)-1-(p-mathoxyphenyl)propyl-1- amine, obtained by a new resolution procedure, exhibits moderate selectivity in the reaction with 2-acetoxyketene; the (S)-(-)-1-(p-methoxyphenyl)propyl group can be oxidatively cleaved from the resultant β-lactam, an important precursor for taxane semi-synthesis.
- Brown, Stephen,Jordan, Allan M.,Lawrence, Nicholas J.,Pritchard, Robin G.,McGown, Alan T.
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p. 3559 - 3562
(2007/10/03)
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- Deoxy taxols
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Rg is C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, or a radical of the formula --W--Rx in which W is a bond, C2-6 alkenediyl, or --(CH2)t --, in which t is one to six; and Rx is naphthyl, phenyl, or heteroaryl, and furthermore Rx can be optionally substituted with one to three same or different C1-6 alkyl, C1-6 alkoxy, halogen or --CF3 groups; R2 is --OCOR, H, OH, --OR, --OSO2 R, --OCONRo R, --OCONHR, --OCOO(CH2)t R, or --OCOOR; and R and Ro are independently C1-6 alkyl, C2-6 alkenyl, C3-6 cycloalkyl, C2-6 alkynyl, or phenyl, optionally substituted with one to three same or different C1-6 alkyl, C1-6 alkoxy, halogen or --CF3 groups. Further provided by this invention are pharmaceutical formulations and intermediates for the the preparation of deoxy taxols of formula I. A method of treating mammalian tumors using a compound of formula I is also provided.
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- Synthesis of carbon-14 labeled Taxolo (paclitaxel)
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Reductive cleavage of the C13 side chain of Taxolo (1, paclitaxel) followed by regioselective silylation gave 7-triethylsilylbaccatin III (4). 3-O-Triethylsilylation of 5 and subsequent reaction with benzoyl chloride-C7-14C gave azetidinone 7. Coupling of 4 and 7 followed by deprotection gave 1.26 g of Taxol-N3'14C (11) having a specific activity of 26.5 mCi/mmol and a radiochemical purity of 95%.
- Walker,Swigor,Kant,Schroeder
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p. 973 - 980
(2007/10/02)
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- Studies on the photochemistry of taxol
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Irradiation of taxol at 280 nm in a Rayonet reactor yielded a novel pentacyclic derivative containing a new bond between C-3 and C-11. The proposed mechanism involves a triplet intermediate and the first event of the oxa-di-π-methane rearrangement. Taxane
- Chen,Farina,Huang,Gao,Golik,Doyle
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p. 8633 - 8650
(2007/10/02)
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- A highly efficient route to taxotere by the β-lactam synthon method
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Taxotere, a highly promising anticancer drug, is synthesized through an efficient coupling of 7,10-diTroc-10-deacetylbaccatin III with enantiomerically pure (3R,4S)-1-tBOC-3-EEO- 4-phenylazetidin-2-one which is obtained via chiral ester enolate - imine cyclocondensation.
- Ojima, Iwao,Sun, Chung Ming,Zucco, Martine,Park, Young Boon,Duclos, Olivier,Kuduk, Scott
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p. 4149 - 4152
(2007/10/02)
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- 7,8-cyclopropataxanes
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An antitumor compound of formula I STR1 in which R1 is --CORz in which Rz is t-butyloxy, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, or phenyl, optionally substituted with one to three same or different C1-6 alkyl, C1-6 alkoxy, halogen or --CF3 groups; R2 is C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, or a radical of the formula --W--Rx in which W is a bond, C2-6 alkenediyl, or --(CH2)t --, in which t is one to six; and Rx is naphthyl, furyl, thienyl or phenyl, and furthermore Rx can be optionally substituted with one to three same or different C1-6 alkyl, C1-6 alkoxy, halogen or --CF3 groups; R3 is OCOR, --OCOOR, H, or OH; R4 is hydrogen; or R3 and R4 jointly form a carbonyl group; and R is C1-6 alkyl. Also provided by this invention are pharmaceutical formulations (compositions) and a method of treating mammalian tumors with a compound of formula I.
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- Phosphonooxy and carbonate derivatives of taxol
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The present invention is directed to novel taxol derivatives useful as anti-tumor agents. Also provided by this invention is pharmaceutical formulations and methods of treating mammalian tumors with the compounds of this invention.
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