BOC-7-氯-DL-色氨酸 | 870481-87-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: BOC-7-氯-DL-色氨酸
• 英文名称: Boc-7-chloro-DL-tryptophan
• 英文别名: 3-(7-chloro-1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 870481-87-1
• 化学式: C₁₆H₁₉ClN₂O₄
• 分子量: 338.791
• InChiKey: BNBNYLGDKIBCCF-UHFFFAOYSA-N

物化性质

• 沸点：
  560.8±50.0 °C(Predicted)
• 密度：
  1.338±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  91.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  BOC-7-氯-DL-色氨酸 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 magnesium sulfate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 [2-(7-Chloro-1H-indol-3-yl)-1-methylaminomethyl-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Structure–activity relationship study of novel necroptosis inhibitors

  摘要：

  Necroptosis is a regulated caspase-independent cell death mechanism that results in morphological features resembling necrosis. It can be induced in a FADD-deficient variant of human Jurkat T cells treated with TNF-alpha. 5-(1H-Indol-3-ylmethyl)-2-thiohydantoins and 5-(1H-indol-3-ylmethyl)hydantoins were found to be potent necroptosis inhibitors (called necrostatins). A SAR study revealed that several positions of the indole were intolerant of substitution, while small substituents at the 7-position resulted in increased inhibitory activity. The hydantoin ring was also quite sensitive to structural modifications. A representative member of this compound class demonstrated moderate pharmacokinetic characteristics and readily entered the central nervous system upon intravenous administration. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.077
• 作为产物：
  描述：

  7-氯吲哚 在 盐酸 、 sodium hydroxide 、 碳酸氢钠 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙酸乙酯 、 甲苯 为溶剂， 反应 172.0h， 生成 BOC-7-氯-DL-色氨酸
  参考文献：
  名称：

  Structure–activity relationship study of novel necroptosis inhibitors

  摘要：

  Necroptosis is a regulated caspase-independent cell death mechanism that results in morphological features resembling necrosis. It can be induced in a FADD-deficient variant of human Jurkat T cells treated with TNF-alpha. 5-(1H-Indol-3-ylmethyl)-2-thiohydantoins and 5-(1H-indol-3-ylmethyl)hydantoins were found to be potent necroptosis inhibitors (called necrostatins). A SAR study revealed that several positions of the indole were intolerant of substitution, while small substituents at the 7-position resulted in increased inhibitory activity. The hydantoin ring was also quite sensitive to structural modifications. A representative member of this compound class demonstrated moderate pharmacokinetic characteristics and readily entered the central nervous system upon intravenous administration. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.077

文献信息

• Structure–activity relationship study of novel necroptosis inhibitors
  作者：Xin Teng、Alexei Degterev、Prakash Jagtap、Xuechao Xing、Sungwoon Choi、Régine Denu、Junying Yuan、Gregory D. Cuny

  DOI：10.1016/j.bmcl.2005.07.077

  日期：2005.11

  Necroptosis is a regulated caspase-independent cell death mechanism that results in morphological features resembling necrosis. It can be induced in a FADD-deficient variant of human Jurkat T cells treated with TNF-alpha. 5-(1H-Indol-3-ylmethyl)-2-thiohydantoins and 5-(1H-indol-3-ylmethyl)hydantoins were found to be potent necroptosis inhibitors (called necrostatins). A SAR study revealed that several positions of the indole were intolerant of substitution, while small substituents at the 7-position resulted in increased inhibitory activity. The hydantoin ring was also quite sensitive to structural modifications. A representative member of this compound class demonstrated moderate pharmacokinetic characteristics and readily entered the central nervous system upon intravenous administration. (c) 2005 Elsevier Ltd. All rights reserved.