444307-65-7Relevant academic research and scientific papers
Synthesis of 7,9-dideoxybaccatin IV analogs from sinenxan A
Zhang, Meng,Yin, Dali,Guo, Ji-Yu,Liang, Xiao-Tian
, p. 5519 - 5527 (2007/10/03)
Sinenxan A, a taxoid isolated from callus tissue cultures of Taxus yunnanensis was converted into 13-oxo-7,9-dideoxy-2-debenzoyl-2-acetyl-baccatin IV and 7,9-dideoxy-2-debenzoyl-4-deacetyl-baccatin IV, a key framework of 1,7,9-trideoxypaclitaxel. Several special steps in this transformation are worthy of note: (1) deoxygenation by treatment with hypophosphorous acid at C-14 position; (2) a highly regioselective O-deacetylation of taxanes at C-5 position; and (3) stereoselective reduction of the 13-carbonyl group by transannular assistance from the C-4-hydroxyl.
Synthesis and biological evaluation of taxinine analogues as orally active multidrug resistance reversal agents in cancer
Zhao, Xin,Gu, Jun,Yin, Dali,Chen, Xiaoguang
, p. 4767 - 4770 (2007/10/03)
Three novel taxinine analogues were prepared and tested for their activity as multidrug resistance (MDR) reversal agents in comparison with verapamil. In vitro testing demonstrated that compounds 8-10 possess MDR-reversal activity in the KB/V cell line. In accumulation assay, the intracellular rhodamine123 concentration increased significantly after treatment with compound 9, higher than that of verapamil in KB/V cell line. In vivo studies with VCR-resistant KB/V tumor xenografts showed that 9 in combination with VCR significantly inhibited tumor growth. Treatment with VCR or 9 alone did not result in growth inhibition. Three novel taxinine analogues were prepared and tested for their activity as multidrug resistance (MDR) reversal agents in comparison with verapamil. In vitro testing demonstrated that compounds 8-10 possess MDR-reversal activity in the KB/V cell line. Half-hour after treatment with 5, 10, and 20 μmol/L compound 9, the intracellular rhodamine123 concentration increased 2.3, 2.9, and 3.2-fold, respectively, higher than 1.88-fold of 10 μmol/L verapamil in KB/V cell line. In vivo studies with VCR-resistant KB/V tumor xenografts showed that compound 9 in combination with VCR significantly inhibited tumor growth. Treatment with VCR or 9 alone did not result in growth inhibition. These results reveal that three taxinine analogues are good modifiers of MDR in tumor cells.
