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学科主题: 药学
题名:
Design, Synthesis, and Antibacterial Activities of Conformationally Constrained Kanamycin A Derivatives
作者: Zhang, Wenxuan1; Chen, Ying1; Liang, Qingzhao1; Li, Hui1; Jin, Hongwei2; Zhang, Liangren2; Meng, Xiangbao1; Li, Zhongjun1
刊名: JOURNAL OF ORGANIC CHEMISTRY
发表日期: 2013-01-18
DOI: 10.1021/jo302247x
卷: 78, 期:2, 页:400-409
收录类别: SCI ; IC
文章类型: Article
WOS标题词: Science & Technology
类目[WOS]: Chemistry, Organic
研究领域[WOS]: Chemistry
关键词[WOS]: RESISTANT BACTERIAL STRAINS ; AMINOGLYCOSIDE ANTIBIOTICS ; CRYSTAL-STRUCTURE ; RIBOSOMAL-RNA ; MOLECULAR RECOGNITION ; X-RAY ; ELECTROSTATIC INTERACTIONS ; STRUCTURAL-ANALYSIS ; BINDING MODES ; SITE
英文摘要:

A series of conformationally constrained kanamycin A derivatives with a 2′-hydroxyl group in ring I and a 5-hydroxyl group in ring II tethered by carbon chains were designed and synthesized. Pivotal 5,2′-hydroxyl groups were exposed, and the kanamycin A intermediate was synthesized from 5, 2′, 4 ′′, 6 ′′-di-O-benzylidene-protected tetraazidokanamycin A. Cyclic kanamycin A derivatives with intramolecular 8-, 9-, 10-, and 11-membered ethers were then prepared by cesium carbonate mediated Williamson ether synthesis or a ring-closing metathesis reaction. The kanamycin A derivatives were assayed against both susceptible and resistant bacterial strains. Although no derivative showed better antibacterial activities than kanamycin A, the antibacterial activities of these cyclic kanamycin A derivatives indeed varied with the length of the bridge. Moreover, different variations of activities were observed between the susceptible and resistant bacterial strains. More tightly constrained derivative 2 with a one-carbon bridge showed better activity than the others against susceptible strains, but it was much less effective for resistant bacterial strains than derivative 3 with a two-carbon bridge and derivative 6 with an unsaturated four-carbon bridge.

语种: 英语
所属项目编号: 2012CB822100 ; 2012ZX09502001-001
项目资助者: National Basic Research Program of China ; Ministry of Science and Technology of China
WOS记录号: WOS:000314008700020
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.bjmu.edu.cn/handle/400002259/59718
Appears in Collections:北京大学药学院_化学生物学系_期刊论文

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作者单位: 1.Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Dept Biol Chem, Beijing 100191, Peoples R China
2.Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Dept Med Chem, Beijing 100191, Peoples R China

Recommended Citation:
Zhang, Wenxuan,Chen, Ying,Liang, Qingzhao,et al. Design, Synthesis, and Antibacterial Activities of Conformationally Constrained Kanamycin A Derivatives[J]. JOURNAL OF ORGANIC CHEMISTRY,2013,78(2):400-409.
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