(S)-2-(2-Chloro-phenyl)-8-oxo-5,6,7,8-tetrahydro-1H-1,4,7a-triaza-s-indacene-7-carboxylic acid | 947733-10-0

• 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: (S)-2-(2-Chloro-phenyl)-8-oxo-5,6,7,8-tetrahydro-1H-1,4,7a-triaza-s-indacene-7-carboxylic acid
• CAS: 947733-10-0
• 化学式: C₁₆H₁₂ClN₃O₃
• 分子量: 329.743
• InChiKey: WEWVGLFEHHBDPB-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  87.98
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-2-(2-Chloro-phenyl)-8-oxo-5,6,7,8-tetrahydro-1H-1,4,7a-triaza-s-indacene-7-carboxylic acid 在 四(三苯基膦)钯 、 1,3-二甲基巴比妥酸 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.25h， 生成 (12S)-5-(2-chlorophenyl)-N-[(3S)-2-hydroxy-5-oxooxolan-3-yl]-2-oxo-1,4,8-triazatricyclo[7.3.0.03,7]dodeca-3(7),5,8-triene-12-carboxamide
  参考文献：
  名称：

  Synthesis and evaluation of tricyclic pyrrolopyrimidinones as dipeptide mimetics: Inhibition of interleukin-1β-converting enzyme

  摘要：

  The application of a tricyclic pyrrolopyrimidinone scaffold for the synthesis of peptidomimetic inhibitors of interleukin-1 beta-converting enzyme (ICE) is reported. The synthesis of the tricyclic scaffold and conversion of it to a variety of target ICE inhibitors were accomplished in 4-5 steps. In vitro biological evaluation of the tricyclic pyrrolopyrimidinones revealed fair to good ICE inhibitors, with the most active compound exhibiting an IC50 of 14 nM in a caspase-1 enzyme binding assay. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.046
• 作为产物：
  描述：

  2-(2-chlorophenyl)-8-oxo-5,6,7,8-tetrahydro-1H-1,4,7a-triaza-s-indacene-7-carboxylic acid ethyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 15.0h， 生成 (S)-2-(2-Chloro-phenyl)-8-oxo-5,6,7,8-tetrahydro-1H-1,4,7a-triaza-s-indacene-7-carboxylic acid
  参考文献：
  名称：

  Synthesis and evaluation of tricyclic pyrrolopyrimidinones as dipeptide mimetics: Inhibition of interleukin-1β-converting enzyme

  摘要：

  The application of a tricyclic pyrrolopyrimidinone scaffold for the synthesis of peptidomimetic inhibitors of interleukin-1 beta-converting enzyme (ICE) is reported. The synthesis of the tricyclic scaffold and conversion of it to a variety of target ICE inhibitors were accomplished in 4-5 steps. In vitro biological evaluation of the tricyclic pyrrolopyrimidinones revealed fair to good ICE inhibitors, with the most active compound exhibiting an IC50 of 14 nM in a caspase-1 enzyme binding assay. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.046