N-[(3S)-2-ethoxy-5-oxotetrahydrofuran-3-yl]-1-{[2-(1-naphthoyl)hydrazino]carbonyl}cyclopentanecarboxamide | 909029-67-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[(3S)-2-ethoxy-5-oxotetrahydrofuran-3-yl]-1-{[2-(1-naphthoyl)hydrazino]carbonyl}cyclopentanecarboxamide
• CAS: 909029-67-0
• 化学式: C₂₄H₂₇N₃O₆
• 分子量: 453.495
• InChiKey: ZMHSZTYQUYLHFO-YMXDCFFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  122.83
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-[(3S)-2-ethoxy-5-oxotetrahydrofuran-3-yl]-1-{[2-(1-naphthoyl)hydrazino]carbonyl}cyclopentanecarboxamide 在 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以0.054 g的产率得到N-[(3S)-2-hydroxy-5-oxooxolan-3-yl]-1-[(naphthalene-1-carbonylamino)carbamoyl]cyclopentane-1-carboxamide
  参考文献：
  名称：

  Synthesis and evaluation of novel 1-(2-acylhydrazinocarbonyl)-cycloalkyl carboxamides as interleukin-1β converting enzyme (ICE) inhibitors

  摘要：

  Novel 1-(2-acylhydrazinocarbonyl)cycloalkyl carboxamides were designed as peptidomimetic inhibitors of interleukin-1 beta converting enzyme (ICE). A short synthesis was developed and moderately potent ICE inhibitors were identified (IC50 values < 100 nM). Most of the synthesized examples were selective for ICE versus the related cysteine proteases caspase-3 and caspase-8, although several dual-acting inhibitors of ICE and caspase-8 were identified. Several of the more potent ICE inhibitors were also shown to inhibit IL-1 beta production in a whole cell assay (IC50 < 500 nM). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.076
• 作为产物：
  描述：

  1,1-环戊基二羧酸 在 四(三苯基膦)钯 1,3-二甲基巴比妥酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 168001.0h， 生成 N-[(3S)-2-ethoxy-5-oxotetrahydrofuran-3-yl]-1-{[2-(1-naphthoyl)hydrazino]carbonyl}cyclopentanecarboxamide
  参考文献：
  名称：

  Synthesis and evaluation of novel 1-(2-acylhydrazinocarbonyl)-cycloalkyl carboxamides as interleukin-1β converting enzyme (ICE) inhibitors

  摘要：

  Novel 1-(2-acylhydrazinocarbonyl)cycloalkyl carboxamides were designed as peptidomimetic inhibitors of interleukin-1 beta converting enzyme (ICE). A short synthesis was developed and moderately potent ICE inhibitors were identified (IC50 values < 100 nM). Most of the synthesized examples were selective for ICE versus the related cysteine proteases caspase-3 and caspase-8, although several dual-acting inhibitors of ICE and caspase-8 were identified. Several of the more potent ICE inhibitors were also shown to inhibit IL-1 beta production in a whole cell assay (IC50 < 500 nM). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.076