(S)-3-{(S)-3-Methyl-2-[2-(naphthalen-1-yloxy)-acetylamino]-butyrylamino}-4-oxo-5-(4-oxo-4H-benzo[d][1,2,3]triazin-3-yloxy)-pentanoic acid tert-butyl ester | 265119-59-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (S)-3-{(S)-3-Methyl-2-[2-(naphthalen-1-yloxy)-acetylamino]-butyrylamino}-4-oxo-5-(4-oxo-4H-benzo[d][1,2,3]triazin-3-yloxy)-pentanoic acid tert-butyl ester
• CAS: 265119-59-3
• 化学式: C₃₃H₃₇N₅O₈
• 分子量: 631.685
• InChiKey: WZWHCDLXJQDWEW-QCDSWUKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  46.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  167.81
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (S)-3-{(S)-3-Methyl-2-[2-(naphthalen-1-yloxy)-acetylamino]-butyrylamino}-4-oxo-5-(4-oxo-4H-benzo[d][1,2,3]triazin-3-yloxy)-pentanoic acid tert-butyl ester 在 苯甲醚 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到(S)-3-{(S)-3-Methyl-2-[2-(naphthalen-1-yloxy)-acetylamino]-butyrylamino}-4-oxo-5-(4-oxo-4H-benzo[d][1,2,3]triazin-3-yloxy)-pentanoic acid
  参考文献：
  名称：

  Structure–activity relationships within a series of caspase inhibitors. Part 2: Heterocyclic warheads

  摘要：

  Various heterocyclic hetero-methyl ketones of the 1-naphthyloxyacetyl-Val-Asp backbone have been prepared. A study of their structure-activity relationship (SAR) related to caspase-1, -3, -6, and -8 is reported. Their efficacy in a cellular model of cell death is also discussed. Potent broad-spectrum caspase inhibitors have been identified. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.036
• 作为产物：
  描述：

  (S)-2-{(S)-3-Methyl-2-[2-(naphthalen-1-yloxy)-acetylamino]-butyrylamino}-succinic acid 4-tert-butyl ester 1-methyl ester 在 N-甲基吗啉 、 potassium fluoride 、 lithium hydroxide 、 氢溴酸 、 sodium iodide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.83h， 生成 (S)-3-{(S)-3-Methyl-2-[2-(naphthalen-1-yloxy)-acetylamino]-butyrylamino}-4-oxo-5-(4-oxo-4H-benzo[d][1,2,3]triazin-3-yloxy)-pentanoic acid tert-butyl ester
  参考文献：
  名称：

  Structure–activity relationships within a series of caspase inhibitors. Part 2: Heterocyclic warheads

  摘要：

  Various heterocyclic hetero-methyl ketones of the 1-naphthyloxyacetyl-Val-Asp backbone have been prepared. A study of their structure-activity relationship (SAR) related to caspase-1, -3, -6, and -8 is reported. Their efficacy in a cellular model of cell death is also discussed. Potent broad-spectrum caspase inhibitors have been identified. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.036