4-methyl-2-(1-propynyl)-1H-imidazole | 1305244-20-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-methyl-2-(1-propynyl)-1H-imidazole
• 英文别名: 5-methyl-2-prop-1-ynyl-1H-imidazole
• CAS: 1305244-20-5
• 化学式: C₇H₈N₂
• 分子量: 120.154
• InChiKey: CARCVKNTZBWXKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-methyl-2-(1-propynyl)-1H-imidazole 、 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl chloride 以 苯 为溶剂， 以24%的产率得到1-(2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl)-4-methyl-2-(1-propynyl)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
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到4-methyl-2-(1-propynyl)-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

• US9187496B2
  申请人：——

  公开号：US9187496B2

  公开（公告）日：2015-11-17