1-methylpiperidin-4-yl 2-cyanoacetate | 910472-15-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-methylpiperidin-4-yl 2-cyanoacetate
• 英文别名: cyanoacetic acid 1-methyl-piperidin-4-yl ester；(1-Methylpiperidin-4-yl) 2-cyanoacetate；(1-methylpiperidin-4-yl) 2-cyanoacetate
• CAS: 910472-15-0
• 化学式: C₉H₁₄N₂O₂
• 分子量: 182.222
• InChiKey: XPANRTAOMIOWQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-methylpiperidin-4-yl 2-cyanoacetate 在 吗啉 、 4-二甲氨基吡啶 、 sulfur 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成
  参考文献：
  名称：

  A new class of small molecule RNA polymerase inhibitors with activity against Rifampicin-resistant Staphylococcus aureus1

  摘要：

  The RNA polymerase holoenzyme is a proven target for antibacterial agents. A high-throughput screening program based on this enzyme from Staphylococcus aureus had previously identified a 2-ureidothiophene-3-carboxylate as a low micromolar inhibitor. An investigation of the relationships between the structures of this class of compounds and their inhibitory- and antibacterial activities is described here, leading to a set of potent RNA polymerase inhibitors with antibacterial activity. Characterization of this bioactivity, including studies of the mechanism of action, is provided, highlighting the power of the reverse chemical genetics approach in providing tools to inhibit the bacterial RNA polymerase. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.035
• 作为产物：
  描述：

  1-甲基-4-哌啶醇 、 氰乙酸 在 N,N'-二环己基碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 3.5h， 以52%的产率得到1-methylpiperidin-4-yl 2-cyanoacetate
  参考文献：
  名称：

  A new class of small molecule RNA polymerase inhibitors with activity against Rifampicin-resistant Staphylococcus aureus1

  摘要：

  The RNA polymerase holoenzyme is a proven target for antibacterial agents. A high-throughput screening program based on this enzyme from Staphylococcus aureus had previously identified a 2-ureidothiophene-3-carboxylate as a low micromolar inhibitor. An investigation of the relationships between the structures of this class of compounds and their inhibitory- and antibacterial activities is described here, leading to a set of potent RNA polymerase inhibitors with antibacterial activity. Characterization of this bioactivity, including studies of the mechanism of action, is provided, highlighting the power of the reverse chemical genetics approach in providing tools to inhibit the bacterial RNA polymerase. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.035

文献信息

• Isoxazole chemistry. 5. N-Alkylation and N-acylation of 5-amino-3-(5-nitro-2-furyl)isoxazoles
  作者：R. G. Micetich、R. Raap、C. G. Chin

  DOI：10.1021/jm00291a020

  日期：1971.9
• A new class of small molecule RNA polymerase inhibitors with activity against Rifampicin-resistant Staphylococcus aureus1
  作者：Francis Arhin、Odette Bélanger、Stéphane Ciblat、Mohammed Dehbi、Daniel Delorme、Evelyne Dietrich、Dilip Dixit、Yanick Lafontaine、Dario Lehoux、Jing Liu、Geoffrey A. McKay、Greg Moeck、Ranga Reddy、Yannick Rose、Ramakrishnan Srikumar、Kelly S.E. Tanaka、Daniel M. Williams、Philippe Gros、Jerry Pelletier、Thomas R. Parr、Adel Rafai Far

  DOI：10.1016/j.bmc.2006.05.035

  日期：2006.9

  The RNA polymerase holoenzyme is a proven target for antibacterial agents. A high-throughput screening program based on this enzyme from Staphylococcus aureus had previously identified a 2-ureidothiophene-3-carboxylate as a low micromolar inhibitor. An investigation of the relationships between the structures of this class of compounds and their inhibitory- and antibacterial activities is described here, leading to a set of potent RNA polymerase inhibitors with antibacterial activity. Characterization of this bioactivity, including studies of the mechanism of action, is provided, highlighting the power of the reverse chemical genetics approach in providing tools to inhibit the bacterial RNA polymerase. (c) 2006 Elsevier Ltd. All rights reserved.