Synthesis and cytotoxic activity of novel 10-alkylated docetaxel analogs. 1998

K Nakayama, and H Terasawa, and I Mitsui, and S Ohsuki, and K Uoto, and S Iimura, and T Soga
New Product Research Laboratories IV, Daiichi Pharmaceutical Co., Ltd., Tokyo, Japan.

An alkylation method of docetaxel at the C-10 position has been established by a radical coupling reaction using a 10-xanthate derivative of 7-O-TES-10-deacetylbaccatin III and appropriate alkenes. In addition the cytotoxic activity of 10-alkylated docetaxel analogs was evaluated. Among these analogs, a derivative having a methoxycarbonyl group at the end of the alkyl moiety exhibited more potent cytotoxic activity than docetaxel.

UI MeSH Term Description Entries
D008958 Models, Molecular Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures. Molecular Models,Model, Molecular,Molecular Model
D000077143 Docetaxel A semisynthetic analog of PACLITAXEL used in the treatment of locally advanced or metastatic BREAST NEOPLASMS and NON-SMALL CELL LUNG CANCER. Docetaxel Anhydrous,Docetaxel Hydrate,Docetaxel Trihydrate,Docetaxol,N-Debenzoyl-N-tert-butoxycarbonyl-10-deacetyltaxol,NSC 628503,RP 56976,RP-56976,Taxoltere Metro,Taxotere,N Debenzoyl N tert butoxycarbonyl 10 deacetyltaxol,RP56976
D000478 Alkylation The covalent bonding of an alkyl group to an organic compound. It can occur by a simple addition reaction or by substitution of another functional group. Alkylations
D000972 Antineoplastic Agents, Phytogenic Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. Antineoplastics, Botanical,Antineoplastics, Phytogenic,Agents, Phytogenic Antineoplastic,Botanical Antineoplastics,Phytogenic Antineoplastic Agents,Phytogenic Antineoplastics
D014407 Tumor Cells, Cultured Cells grown in vitro from neoplastic tissue. If they can be established as a TUMOR CELL LINE, they can be propagated in cell culture indefinitely. Cultured Tumor Cells,Neoplastic Cells, Cultured,Cultured Neoplastic Cells,Cell, Cultured Neoplastic,Cell, Cultured Tumor,Cells, Cultured Neoplastic,Cells, Cultured Tumor,Cultured Neoplastic Cell,Cultured Tumor Cell,Neoplastic Cell, Cultured,Tumor Cell, Cultured
D017239 Paclitaxel A cyclodecane isolated from the bark of the Pacific yew tree, TAXUS BREVIFOLIA. It stabilizes MICROTUBULES in their polymerized form leading to cell death. 7-epi-Taxol,Anzatax,Bris Taxol,NSC-125973,Onxol,Paclitaxel, (4 alpha)-Isomer,Paxene,Praxel,Taxol,Taxol A,7 epi Taxol,NSC 125973,NSC125973,Taxol, Bris
D043823 Taxoids A group of diterpenoid CYCLODECANES named for the taxanes that were discovered in the TAXUS tree. The action on MICROTUBULES has made some of them useful as ANTINEOPLASTIC AGENTS. Taxanes,Taxoid

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