2-<2-(6-Cyanindol-2-yl)-(E)-vinyl>-1-benzofuran-5-carbonitril | 105190-93-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-<2-(6-Cyanindol-2-yl)-(E)-vinyl>-1-benzofuran-5-carbonitril
• 英文别名: NU-126；2-[(E)-2-(5-cyano-1-benzofuran-2-yl)ethenyl]-1H-indole-6-carbonitrile
• CAS: 105190-93-0
• 化学式: C₂₀H₁₁N₃O
• 分子量: 309.327
• InChiKey: HHROCCWCQGKIDY-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-<2-(6-Cyanindol-2-yl)-(E)-vinyl>-1-benzofuran-5-carbonitril 以71%的产率得到
  参考文献：
  名称：

  DANN, O.;CHAR, H.;FLEISCHMANN, P.;FRICKE, H., LIEBIGS ANN. CHEM., 1986, N 3, 438-455

  摘要：

  DOI：
• 作为产物：
  描述：

  6-溴吲哚-2-甲醛 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 2-<2-(6-Cyanindol-2-yl)-(E)-vinyl>-1-benzofuran-5-carbonitril
  参考文献：
  名称：

  Dann, Otto; Char, Helmut; Fleischmann, Paul, Liebigs Annalen der Chemie, 1986, # 3, p. 438 - 455

  摘要：

  DOI：

文献信息

• Novel benzofuran inhibitors of human mitogen-activated protein kinase phosphatase-1
  作者：John S. Lazo、Ruth Nunes、John J. Skoko、Pierre E. Queiroz de Oliveira、Andreas Vogt、Peter Wipf

  DOI：10.1016/j.bmc.2006.04.036

  日期：2006.8

  Protein tyrosine phosphatases have a central role in the maintenance of normal cellular functionality. For example, PTP1B has been implicated in insulin-resistance, obesity, and neoplasia. Mitogen-activated protein kinase phosphatase-1 (MKP-1 or DUSP1) dephosphorylates and inactivates mitogen-activated protein kinase (MAPK) substrates, such as p38, JNK, and Erk, and has been implicated in neoplasia. The lack of readily available selective small molecule inhibitors of MKP family members has severely limited interrogation of their biological role. Inspired by a previously identified inhibitor (NSC 357756) of MKP-3, we synthesized seven NSC 357756 congeners, which were evaluated for in vitro inhibition against several protein phosphatases. Remarkably, none displayed potent inhibition against MKP-3, including the desamino NSC 357756 analog NU-154. Interestingly, NU-154 inhibited human PTP1B in vitro with an IC50 value of 24 +/- 1 mu M and showed little inhibition against Cdc25B, MKP-1, and VHR phosphatases. NU- 126 [2-((E)-2-(5-cyanobenzofuran-2-yl)vinyl)-1H-indole-6-carbonitrile] inhibited MKP-1 and VHR in vitro but was less active against human MKP-3, Cdc25B, and PTP1B. The inhibition of MKP-1 by NU-126 was independent of redox processes. The benzofuran substructure represents a new potential scaffold for further analog development and provides encouragement that more selective and potent inhibitors of MKP family members may be achievable. (c) 2006 Elsevier Ltd. All rights reserved.
• Dann, Otto; Char, Helmut; Fleischmann, Paul, Liebigs Annalen der Chemie, 1986, # 3, p. 438 - 455
  作者：Dann, Otto、Char, Helmut、Fleischmann, Paul、Fricke, Helmut

  DOI：——

  日期：——
• DANN, O.;CHAR, H.;FLEISCHMANN, P.;FRICKE, H., LIEBIGS ANN. CHEM., 1986, N 3, 438-455
  作者：DANN, O.、CHAR, H.、FLEISCHMANN, P.、FRICKE, H.

  DOI：——

  日期：——