N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)(chloro)methanesulfonamide | 1569296-84-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)(chloro)methanesulfonamide
• 英文别名: N-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-1-chloromethanesulfonamide
• CAS: 1569296-84-9
• 化学式: C₉H₂₂ClNO₃SSi
• 分子量: 287.883
• InChiKey: TTYXERJSWNEQBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-硝基咪唑 、 N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)(chloro)methanesulfonamide 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以35%的产率得到N-[2-(tert-butyldimethylsilyloxy)ethyl] (2-nitro-1H-imidazol-1-yl)methanesulfonamide
  参考文献：
  名称：

  Novel nitroimidazole alkylsulfonamides as hypoxic cell radiosensitisers

  摘要：

  A novel class of nitroimidazole alkylsulfonamides have been prepared and evaluated as hypoxia-selective cytotoxins and radiosensitisers. The sulfonamide side chain markedly influences the physicochemical properties of the analogues: lowering aqueous solubility and raising the electron affinity of the nitroimidazole group. The addition of hydroxyl or basic amine groups increased aqueous solubility, with charged amine groups contributing to increased electron affinity. The analogues covered the range of electron affinity for effective radiosensitisation with one-electron reduction potentials ranging from -503 to -342 mV. Cytotoxicity under normoxia or anoxia against a panel of human tumour cell lines was determined using a proliferation assay. 2-Nitroimidazole sulfonamides displayed significant hypoxia-selective cytotoxicity ( 6 to 64-fold), while 4- and 5-nitroimidazole analogues did not display hypoxia-selective cytotoxicity. All analogues sensitised anoxic HCT-116 human colorectal cells to radiation at non-toxic concentrations. 2-Nitroimidazole analogues provided modest sensitisation due to the relatively low concentrations used while several 5-nitroimidazole analogues provided equivalent sensitisation to misonidazole and etanidazole at similar molar concentrations. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.039
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)(chloro)methanesulfonamide
  参考文献：
  名称：

  [EN] NITROIMIDAZOLE COMPOUNDS AND THEIR USE IN CANCER THERAPY
  [FR] COMPOSÉS DE NITROIMIDAZOLE ET LEUR UTILISATION EN THÉRAPIE ANTICANCÉREUSE

  摘要：

  公开号：

  WO2014030142A3

文献信息

• [EN] NITROIMIDAZOLE COMPOUNDS AND THEIR USE IN CANCER THERAPY<br/>[FR] COMPOSÉS DE NITROIMIDAZOLE ET LEUR UTILISATION EN THÉRAPIE ANTICANCÉREUSE
  申请人：AUCKLAND UNISERVICES LTD

  公开号：WO2014030142A3

  公开（公告）日：2014-04-17
• Novel nitroimidazole alkylsulfonamides as hypoxic cell radiosensitisers
  作者：Muriel Bonnet、Cho Rong Hong、Yongchuan Gu、Robert F. Anderson、William R. Wilson、Frederik B. Pruijn、Jingli Wang、Kevin O. Hicks、Michael P. Hay

  DOI：10.1016/j.bmc.2014.02.039

  日期：2014.4

  A novel class of nitroimidazole alkylsulfonamides have been prepared and evaluated as hypoxia-selective cytotoxins and radiosensitisers. The sulfonamide side chain markedly influences the physicochemical properties of the analogues: lowering aqueous solubility and raising the electron affinity of the nitroimidazole group. The addition of hydroxyl or basic amine groups increased aqueous solubility, with charged amine groups contributing to increased electron affinity. The analogues covered the range of electron affinity for effective radiosensitisation with one-electron reduction potentials ranging from -503 to -342 mV. Cytotoxicity under normoxia or anoxia against a panel of human tumour cell lines was determined using a proliferation assay. 2-Nitroimidazole sulfonamides displayed significant hypoxia-selective cytotoxicity ( 6 to 64-fold), while 4- and 5-nitroimidazole analogues did not display hypoxia-selective cytotoxicity. All analogues sensitised anoxic HCT-116 human colorectal cells to radiation at non-toxic concentrations. 2-Nitroimidazole analogues provided modest sensitisation due to the relatively low concentrations used while several 5-nitroimidazole analogues provided equivalent sensitisation to misonidazole and etanidazole at similar molar concentrations. (C) 2014 Elsevier Ltd. All rights reserved.