ethyl (1S)-9-oxo-2,3-dihydro-1H-pyrrolo[2,1-b]quinazoline-1-carboxylate | 866925-48-6

• 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: ethyl (1S)-9-oxo-2,3-dihydro-1H-pyrrolo[2,1-b]quinazoline-1-carboxylate
• CAS: 866925-48-6
• 化学式: C₁₄H₁₄N₂O₃
• 分子量: 258.277
• InChiKey: JFMRKAAYWJBOST-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (1S)-9-oxo-2,3-dihydro-1H-pyrrolo[2,1-b]quinazoline-1-carboxylate 在 sodium hydroxide 、 四(三苯基膦)钯 、 1,3-二甲基巴比妥酸 作用下， 以 甲醇 为溶剂， 生成
  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：

  邻氨基苯甲酸甲酯 、 L-焦谷氨酸乙酯 在 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以91%的产率得到ethyl (1S)-9-oxo-2,3-dihydro-1H-pyrrolo[2,1-b]quinazoline-1-carboxylate
  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

文献信息

• Synthesis and evaluation of tricyclic pyrrolopyrimidinones as dipeptide mimetics: Inhibition of interleukin-1β-converting enzyme
  作者：Michael C. Laufersweiler、Yili Wang、David L. Soper、Maureen K. Suchanek、Amy N. Fancher、Wei Lu、Richard L. Wang、Kofi A. Oppong、Christopher D. Ellis、Mark W. Baize、Steven V. O’Neil、John A. Wos、Thomas P. Demuth

  DOI：10.1016/j.bmcl.2005.06.046

  日期：2005.10

  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.