Citation: Shang-Qing XIAO, Yong-Mei CUI, Wei-Qing QIU, Ye-Sha CUI, Hai-Xia LIN. Syntheses and Crystal Studies of Novel C-3'-N-sulfonyl and 7-O-acyl Modified Paclitaxel Analogues[J]. Chinese Journal of Structural Chemistry, ;2021, 40(8): 1088-1097. doi: 10.14102/j.cnki.0254–5861.2011–3116 shu

Syntheses and Crystal Studies of Novel C-3'-N-sulfonyl and 7-O-acyl Modified Paclitaxel Analogues

Department of Chemistry, College of Sciences, Shanghai University, Shanghai 200444, China

Corresponding author: Hai-Xia LIN, haixialin@staff.shu.edu.cn
Received Date: 25 January 2021
Accepted Date: 20 April 2021

Fund Project: the National Natural Science Foundation of China 21272154the National Natural Science Foundation of China 81202402

Figures(5)

Three C-3'-N-sulfonyl and C-7-O-acyl paclitaxel analogues were synthesized from 10-deacetyl baccatin Ⅲ (10-DAB) and their structures were confirmed by ¹H NMR, ¹³C NMR and HR-MS. Among them, the crystal structure of compound 9b was determined by single-crystal X-ray diffraction. Compound 9b crystallizes in monoclinic system, space group P2₁ with a = 12.395(4), b = 15.215(5), c = 14.905(5) Å, β = 105.559(4)° and Z = 2. In the structure, the introduction of the hydrophobic 3-fluorobenzoyl group at C(7) has little effect on the conformation of tetracyclic system. However, the conformation of the side-chain at C(13) in 9b is quite different from that of paclitaxel and docetaxel.
- paclitaxel,
- 3'-N-sulfonyl,
- crystal structure,
- bioactivity,
- conformation
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