103150-33-0Relevant articles and documents
Docetaxel side chain 2'-derived novel taxanes antitumor compound as well as synthesis method and application thereof
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, (2017/08/29)
The invention discloses a docetaxel side chain 2'-derived novel taxanes antitumor compound shown as the general structure formula (I) as well as a synthesis method and application thereof. In the formula, X is N or O, R is H or acetyl, and R' is H, nitryl, cyano, methoxyl or a halogen group. The synthesis method takes 10-deacetylbaccatin is used as a raw material; after 7-OH and 10-OH are protected, condensation with phenylisoserine (side chain) protecting 3'-NHBoc and 2'-OH in the presence of condensation agents DCC (Dicyclohexylcarbodiimide) and DMAP (Dimethylaminopyridine) is performed; esterification with substituted phenyl isoxazole carboxylic acid or substituted phenyl oxadiazole methyl carboxylic acid in the presence of the DCC and the DMAP is performed; finally, a protecting group is removed to obtain the compound. The compound disclosed by the invention has relatively high activity on tumor cells.
Enantioselective total synthesis of (-)-taxol
Kusama, Hiroyuki,Hara, Ryoma,Kawahara, Shigeru,Nishimori, Toshiyuki,Kashima, Hajime,Nakamura, Nobuhito,Morihira, Koichiro,Kuwajima, Isao
, p. 3811 - 3820 (2007/10/03)
Enantioselective total synthesis of taxol has been accomplished. Coupling reaction of the optically pure A-ring hydroxy aldehyde with the aromatic C-ring fragment followed by Lewis acid mediated eight-membered B- ring cyclization gave the desired ABC endo-tricarbocycle. The C-ring moiety of this product was reduced under Birch conditions to the cyclohexadiene derivative, which was oxygenated by singlet oxygen from the convex β-face to give the C4β,C7β-diol stereoselectively. For introduction of the C19- methyl, the cyclopropyl ketone was prepared via cyclopropanation of the C- ring allylic alcohol or conjugate addition of a cyano group to the C-ring enone. Reductive cleavage of the cyclopropane ring followed by isomerization of the resulting enol to the corresponding ketone gave the crucial synthetic intermediate containing the C19-methyl group. Regioselective transformation of three hydroxyl groups of this intermediate, conversion of the C4-carbonyl group to the allyl chloride, and introduction of the C10-oxygen functionality afforded a precursor for D-ring construction. Dihydroxylation of the allyl chloride moiety followed by basic treatment of the resulting diol gave a fully functionalized taxol skeleton. Functional group manipulation of this product including attachment of the C13 side chain provided (-)-taxol.
Design and synthesis of a taxoid library using radiofrequency encoded combinatorial chemistry
Xiao, Xiao-Yi,Parandoosh, Zahra,Nova, Michael P.
, p. 6029 - 6033 (2007/10/03)
Radiofrequency encoded combinatorial (REC) chemistry is a recently developed nonchemical encoding strategy in library synthesis. Encoded chemical libraries of complex molecular structures like Taxol can be constructed employing the noninvasive REC strategy and novel solid phase synthesis techniques, as demonstrated by the synthesis of the first 400- membered taxoid library in a discrete format and in quantities of multimilligrams/member.
