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

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摘要: 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. )

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	肖上青
	崔永梅
	邱卫清
	崔叶莎
	林海霞

关键词: paclitaxel, 3?-N-sulfonyl, crystal structure, bioactivity, conformation

Abstract: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. )

Key words: paclitaxel 3?-N-sulfonyl crystal structure bioactivity conformation

收稿日期: 2021-01-25 出版日期: 2021-07-28

基金资助:The project was supported by the National Natural Science Foundation of China (Nos. 21272154 and 81202402)

通讯作者: haixialin@staff.shu.edu.cn E-mail: haixialin@staff.shu.edu.cn

引用本文:

肖上青;崔永梅;邱卫清;崔叶莎;林海霞. Syntheses and Crystal Studies of Novel C-3΄-N-sulfonyl and 7-O-acyl Modified Paclitaxel Analogues[J]. 结构化学, 2021, 40(8): 1088-1097.
XIAO Shang-Qing;CUI Yong-Mei;QIU Wei-Qing;CUI Ye-Sha;LIN Hai-Xia. Syntheses and Crystal Studies of Novel C-3΄-N-sulfonyl and 7-O-acyl Modified Paclitaxel Analogues. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2021, 40(8): 1088-1097.

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http://manu30.magtech.com.cn/jghx/CN/ 或 http://manu30.magtech.com.cn/jghx/CN/Y2021/V40/I8/1088

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