Synthesis and biological evaluation of novel A-seco-taxoids derived from 1-deoxybaccatin VI. Issue 2 (17th January 2018)

• Record Type: Journal Article
• Authors: Qiu, Wei-Qing; Cui, Yong-Mei; Tang, Ping; Qiu, Yuan-You; Lin, Hai-Xia
• Is Part Of: Natural product research. Volume 32:Issue 2(2018)
• Page Start: 121
• Page End: 127
• Publication Date: 2018-01-17
• Subjects: Taxoids -- 1-deoxybaccatin VI -- cytotoxic activity -- paclitaxel; Natural products -- Periodicals; Natural products -- Research -- Periodicals; Biological Factors -- Periodicals; Biological Products -- Periodicals; 547
• DOI: 10.1080/14786419.2017.1340281
• Languages: English
• ISSNs: 1478-6419

Abstract

Abstract: Three novel nor-seco-taxoids13, 15, 23 in which the A rings are cleaved but the B, C, and D rings are retained were prepared from 1-deoxybaccatin VI via its nor-dioxo derivative and their structures were confirmed by 1 H NMR, 13 C NMR and high resolution MS. Oxidative introduction of C-1 hydroxyl to 1-deoxybaccatin VI with oxidising agent KBrO3 and catalyst RuCl3 led to the dioxo derivative6 and its structure is determined by X-ray crystallographic analysis. A-seco taxoids13, 15, 23 with a C-13 ester linkage were tested for cytotoxic activity and all compounds showed no measurable cytotoxic activity against HCT-116 cell line. However, 1-deoxy-9a-dihydrotaxane analogue4 semi-synthesised from 1-deoxybaccatin VI is 10-fold less cytotoxic than paclitaxel, indicating the indispensible nature of the A ring double bond for the bioactivity of paclitaxel. Abstract :