2-(N-{2-[(tert-Butoxycarbonyl)amino]ethyl}-N-(tert-butoxycarbonyl)aminomethyl)-4-methoxypyridine-6-carboxylic acid | 216578-02-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(N-{2-[(tert-Butoxycarbonyl)amino]ethyl}-N-(tert-butoxycarbonyl)aminomethyl)-4-methoxypyridine-6-carboxylic acid
• 英文别名: 4-Methoxy-6-[[(2-methylpropan-2-yl)oxycarbonyl-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]amino]methyl]pyridine-2-carboxylic acid
• CAS: 216578-02-8
• 化学式: C₂₀H₃₁N₃O₇
• 分子量: 425.482
• InChiKey: RTVBFGGIVOLALC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(N-{2-[(tert-Butoxycarbonyl)amino]ethyl}-N-(tert-butoxycarbonyl)aminomethyl)-4-methoxypyridine-6-carboxylic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 6-[(2-Amino-ethylamino)-methyl]-4-methoxy-pyridine-2-carboxylic acid [2-(5-nitro-1H-imidazol-4-yl)-ethyl]-amide
  参考文献：
  名称：

  Highficld, Jackie A.; Mehta, Lina K.; Patrick, John, Journal of the Chemical Society. Perkin transactions I, 1999, # 16, p. 2343 - 2351

  摘要：

  DOI：
• 作为产物：
  描述：

  Methyl 6-formyl-4-methoxypyridine-2-carboxylate 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 生成 2-(N-{2-[(tert-Butoxycarbonyl)amino]ethyl}-N-(tert-butoxycarbonyl)aminomethyl)-4-methoxypyridine-6-carboxylic acid
  参考文献：
  名称：

  Synthesis and properties of prodrugs activated in hypoxia to give bleomycin analogues

  摘要：

  Prodrugs bioreductively activated to bleomycin analogues are reported. The production of hydroxyl radicals in the presence of Fe(II) and dioxygen by both the prodrugs and the activated products are determined and their in vitro cytotoxicity measured. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00467-3

文献信息

• Synthesis, hydroxyl radical production and cytotoxicity of analogues of bleomycin
  作者：Jackie A. Highfield、Lina K. Mehta、John Parrick、Peter Wardman

  DOI：10.1016/s0968-0896(00)00042-0

  日期：2000.5

  bleomycin-A2 and were more cytotoxic than the corresponding compounds lacking the DNA binding unit. On exposure of a mixture of cells and prodrugs to hypoxia and then air, the prodrug containing the nitrohistidine unit was not bioreductively activated but the prodrug having an N-oxide group was bioreductively activated. This result represents a novel approach to the improvement of the therapeutic ratio of

  抗癌药博来霉素的金属络合区域的两个吡啶类似物和两个相关但已失活的前药已与作为DNA结合单元的2,6-二苯基吡啶衍生物连接。2，6-二苯基吡啶系统在结构上与博来霉素的细胞毒性的已知放大器有关。发现缀合物比博来霉素-A2更牢固地结合DNA，并且比缺乏DNA结合单元的相应化合物更具细胞毒性。当细胞和前药的混合物暴露于低氧然后暴露于空气中时，含有硝基组氨酸单元的前药未被生物还原活化，但是具有N-氧化物基团的前药被生物还原活化。该结果代表了改善博来霉素类似物的治疗率的新方法。
• Highficld, Jackie A.; Mehta, Lina K.; Patrick, John, Journal of the Chemical Society. Perkin transactions I, 1999, # 16, p. 2343 - 2351
  作者：Highficld, Jackie A.、Mehta, Lina K.、Patrick, John、Candeias, Luis P.、Wardman, Peter

  DOI：——

  日期：——
• Synthesis and properties of prodrugs activated in hypoxia to give bleomycin analogues
  作者：Jackie A. Highfield、Lina K. Mehta、John Parrick、Luis P. Candeias、Peter Wardman

  DOI：10.1016/s0960-894x(98)00467-3

  日期：1998.9

  Prodrugs bioreductively activated to bleomycin analogues are reported. The production of hydroxyl radicals in the presence of Fe(II) and dioxygen by both the prodrugs and the activated products are determined and their in vitro cytotoxicity measured. (C) 1998 Elsevier Science Ltd. All rights reserved.