(S)-2-{(S)-3-Methyl-2-[2-(naphthalen-1-yloxy)-acetylamino]-butyrylamino}-succinic acid 4-tert-butyl ester 1-methyl ester | 265119-56-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-{(S)-3-Methyl-2-[2-(naphthalen-1-yloxy)-acetylamino]-butyrylamino}-succinic acid 4-tert-butyl ester 1-methyl ester
• CAS: 265119-56-0
• 化学式: C₂₆H₃₄N₂O₇
• 分子量: 486.565
• InChiKey: BOWHDXLGVUXFAL-CVDCTZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  120.03
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  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 、 苯甲醚 、 三氟乙酸 、 sodium iodide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.83h， 生成 5-((S)-4-Carboxy-3-{(S)-3-methyl-2-[2-(naphthalen-1-yloxy)-acetylamino]-butyrylamino}-2-oxo-butoxy)-3-methyl-isoxazole-4-carboxylic acid ethyl 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
• 作为产物：
  描述：

  1-萘氧基乙酸 、 L-valinyl-L-aspartyl-β-(tert-butyl ester) methyl ester 在 N-甲基吗啉 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到(S)-2-{(S)-3-Methyl-2-[2-(naphthalen-1-yloxy)-acetylamino]-butyrylamino}-succinic acid 4-tert-butyl ester 1-methyl 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

文献信息

• Structure–Activity relationships within a series of caspase inhibitors: effect of leaving group modifications
  作者：Brett R. Ullman、Teresa Aja、Thomas L. Deckwerth、Jose-Luis Diaz、Julia Herrmann、Vincent J. Kalish、Donald S. Karanewsky、Steven P. Meduna、Kip Nalley、Edward D. Robinson、Silvio P. Roggo、Robert O. Sayers、Albert Schmitz、Robert J. Ternansky、Kevin J. Tomaselli、Joe C. Wu

  DOI：10.1016/s0960-894x(03)00755-8

  日期：2003.10

  Various aryloxy methyl ketones of the 1-naphthyloxyacetyl-Val-Asp backbone have been prepared. A systematic study of their structure-activity relationship (SAR) related to caspases 1, 3, 6, and 8 is reported. Highly potent irreversible broad-spectrum caspase inhibitors have been identified. Their efficacy in cellular models of cell death and inflammation are also discussed. (C) 2003 Elsevier Ltd. All rights reserved.