1-{[2-(trimethylsilyl)ethoxy]methyl}-4-[2-(trimethylsilyl)ethynyl]-1H-imidazole | 1305244-30-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-{[2-(trimethylsilyl)ethoxy]methyl}-4-[2-(trimethylsilyl)ethynyl]-1H-imidazole
• CAS: 1305244-30-7
• 化学式: C₁₄H₂₆N₂OSi₂
• 分子量: 294.544
• InChiKey: PZJVABNNLLWVCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  27.05
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-{[2-(trimethylsilyl)ethoxy]methyl}-4-[2-(trimethylsilyl)ethynyl]-1H-imidazole 在 水 、 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 生成 1-(2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl)-4-ethynylimidazole
  参考文献：
  名称：

  Synthesis and biological evaluation of 1-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]-4-ethynylimidazole. A novel and highly potent anti-inflammatory and cytoprotective agent

  摘要：

  To explore more potent N-acylimidazole analogues of CDDO than CDDO-Im, which is one of the most potent compounds in several widely used bioassays related to protection against inflammation and carcinogenesis; we have synthesized and evaluated five new N-acyl(acetylenic) imidazole analogues. Among them, 4-ethynylimidazole 4 is nearly equivalent to CDDO-Im in potency in these bioassays. Remarkably, the solid form of 4 is more stable than that of CDDO-Im. These findings suggest that 4 is a very promising anti-inflammatory and cytoprotective agent and its further preclinical evaluation is warranted. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.018
• 作为产物：
  描述：

  三甲基乙炔基硅 、 4-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以51%的产率得到1-{[2-(trimethylsilyl)ethoxy]methyl}-4-[2-(trimethylsilyl)ethynyl]-1H-imidazole
  参考文献：
  名称：

  Synthesis and biological evaluation of 1-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]-4-ethynylimidazole. A novel and highly potent anti-inflammatory and cytoprotective agent

  摘要：

  To explore more potent N-acylimidazole analogues of CDDO than CDDO-Im, which is one of the most potent compounds in several widely used bioassays related to protection against inflammation and carcinogenesis; we have synthesized and evaluated five new N-acyl(acetylenic) imidazole analogues. Among them, 4-ethynylimidazole 4 is nearly equivalent to CDDO-Im in potency in these bioassays. Remarkably, the solid form of 4 is more stable than that of CDDO-Im. These findings suggest that 4 is a very promising anti-inflammatory and cytoprotective agent and its further preclinical evaluation is warranted. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.018

文献信息

• Aromatic heterocycle galectin-1 interactions for selective single-digit nM affinity ligands
  作者：Kristoffer Peterson、Patrick M. Collins、Xiaoli Huang、Barbro Kahl-Knutsson、Sofia Essén、Fredrik R. Zetterberg、Stina Oredsson、Hakon Leffler、Helen Blanchard、Ulf J. Nilsson

  DOI：10.1039/c8ra04389b

  日期：——

  A series of 3-triazole-thiogalactosides and 3,3′-triazole-thiodigalactosides substituted with different five-membered heterocycles at the C-4 triazole position were found to have high selectivity for galectin-1.

  一系列在C-4三唑位置上用不同的五元杂环取代的3-三唑硫半乳糖苷和3,3'-三唑硫二半乳糖苷被发现对galectin-1具有高选择性。