- Synthesis and interactions of 7-deoxy-, 10-deacetoxy, and 10-deacetoxy-7-deoxypaclitaxel with NCI/ADR-RES cancer cells and bovine brain microvessel endothelial cells
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7-Deoxypaclitaxel, 10-deacetoxypaclitaxel and 10-deacetoxy-7- deoxypaclitaxel were prepared and evaluated for their ability to promote assembly of tubulin into microtubules, their cytotoxicity against NCI/ADR-RES cells and for their interactions with P-gl
- Ge, Haibo,Vasandani, Veena,Huff, Jacquelyn K.,Audus, Kenneth L.,Himes, Richard H.,Seelig, Anna,Georg, Gunda I.
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p. 433 - 436
(2007/10/03)
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- An efficient semisynthesis of 7-deoxypaclitaxel from taxine
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A semisynthesis of 7-deoxypaclitaxel 4 is described, starting from taxine 6 - the most abundant naturally occurring taxane diterpene fraction. A key step in this transformation is a tandem reaction: stereoselective osmylation of cinnamic ester 14/intramolecularly assisted methanolysis of 16, which gives the key intermediate 5, along with the optically pure ester 17 - a precursor for the synthesis of the paclitaxel side-chain. In this way, the cinnamoyltaxicine 9 is converted into 7-deoxybaccatin III 25 in 11 steps, and in 15% overall yield.
- Saicic, Radomir N.,Matovic, Radomir
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- An efficient semisynthesis of 7-deoxypaclitaxel from taxine
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Highly cytotoxic 7-deoxypaclitaxel analogues are obtained by a semisynthesis starting from taxine - the most abundant naturally occurring taxane diterpene fraction.
- Matovic, Radomir,Saicic, Radomir N.
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p. 1745 - 1746
(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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- 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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- Synthesis of 7-Deoxy- and 7,10-Dideoxytaxol via Radical Intermediates
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7-Deoxytaxol and 7,10-dideoxytaxol were prepared from baccatin III, employing the Barton deoxygenation procedure and the Holton acylation method at C-13.
- Chen, Shu-Hui,Huang, Stella,Kant, Joydeep,Fairchild, Craig,Wei, Jianmei,Farina, Vittorio
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p. 5028 - 5029
(2007/10/02)
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