Ethyl 2-[(2-cyanoacetyl)amino]-4-(4-fluorophenyl)-3-thiophenecarboxylate | 546116-60-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: Ethyl 2-[(2-cyanoacetyl)amino]-4-(4-fluorophenyl)-3-thiophenecarboxylate
• 英文别名: ethyl 2-[(2-cyanoacetyl)amino]-4-(4-fluorophenyl)thiophene-3-carboxylate
• CAS: 546116-60-3
• 化学式: C₁₆H₁₃FN₂O₃S
• 分子量: 332.355
• InChiKey: HRXGFLXLLAVHJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 2-[(2-cyanoacetyl)amino]-4-(4-fluorophenyl)-3-thiophenecarboxylate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到3-(4-fluorophenyl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile
  参考文献：
  名称：

  Discovery and SAR development of thienopyridones: A class of small molecule AMPK activators

  摘要：

  AMP-activated protein kinase (AMPK) is well established as a sensor and regulator of intracellular and whole-body energy metabolism. A high-throughput screen was performed in order to identify chemotypes that are bound by AMPK. A novel thienopyridone compound (1) was identified and subsequently optimized. The structure-activity relationships that emerged from this effort are described. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.011
• 作为产物：
  描述：

  4-氟苯乙酮 在 吗啉 、 五氯化磷 、 sulfur 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 Ethyl 2-[(2-cyanoacetyl)amino]-4-(4-fluorophenyl)-3-thiophenecarboxylate
  参考文献：
  名称：

  Discovery and SAR development of thienopyridones: A class of small molecule AMPK activators

  摘要：

  AMP-activated protein kinase (AMPK) is well established as a sensor and regulator of intracellular and whole-body energy metabolism. A high-throughput screen was performed in order to identify chemotypes that are bound by AMPK. A novel thienopyridone compound (1) was identified and subsequently optimized. The structure-activity relationships that emerged from this effort are described. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.011

文献信息

• Discovery and SAR development of thienopyridones: A class of small molecule AMPK activators
  作者：Gang Zhao、Rajesh R. Iyengar、Andrew S. Judd、Barbara Cool、William Chiou、Lemma Kifle、Ernst Frevert、Hing Sham、Philip R. Kym

  DOI：10.1016/j.bmcl.2007.04.011

  日期：2007.6

  AMP-activated protein kinase (AMPK) is well established as a sensor and regulator of intracellular and whole-body energy metabolism. A high-throughput screen was performed in order to identify chemotypes that are bound by AMPK. A novel thienopyridone compound (1) was identified and subsequently optimized. The structure-activity relationships that emerged from this effort are described. (c) 2007 Elsevier Ltd. All rights reserved.