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Design, Synthesis, and Antibacterial Activities of Conformationally Constrained Kanamycin A Derivatives
Zhang, Wenxuan1; Chen, Ying1; Liang, Qingzhao1; Li, Hui1; Jin, Hongwei2; Zhang, Liangren2; Meng, Xiangbao1; Li, Zhongjun1
刊名JOURNAL OF ORGANIC CHEMISTRY
2013-01-18
DOI10.1021/jo302247x
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
WOS记录号WOS:000314008700020
项目编号2012CB822100 ; 2012ZX09502001-001
资助机构National Basic Research Program of China ; Ministry of Science and Technology of China
引用统计
被引频次:15[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/59718
专题北京大学药学院_化学生物学系
北京大学药学院_天然药物与仿生药物国家重点实验室
北京大学药学院_药物化学系
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
推荐引用方式
GB/T 7714
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.
APA Zhang, Wenxuan.,Chen, Ying.,Liang, Qingzhao.,Li, Hui.,Jin, Hongwei.,...&Li, Zhongjun.(2013).Design, Synthesis, and Antibacterial Activities of Conformationally Constrained Kanamycin A Derivatives.JOURNAL OF ORGANIC CHEMISTRY,78(2),400-409.
MLA Zhang, Wenxuan,et al."Design, Synthesis, and Antibacterial Activities of Conformationally Constrained Kanamycin A Derivatives".JOURNAL OF ORGANIC CHEMISTRY 78.2(2013):400-409.
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