1-(2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl)-2-ethynylimidazole | 1305244-11-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl)-2-ethynylimidazole
• 英文别名: (4aR,6aR,6aS,6bR,8aS,12aS,14bS)-8a-(2-ethynylimidazole-1-carbonyl)-4,4,6a,6b,11,11,14b-heptamethyl-3,13-dioxo-4a,5,6,6a,7,8,9,10,12,12a-decahydropicene-2-carbonitrile
• CAS: 1305244-11-4
• 化学式: C₃₆H₄₃N₃O₃
• 分子量: 565.756
• InChiKey: NRBMMFSDPLCPFY-RDTOLKQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  42
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  92.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-乙炔-1-[[2-(三甲基甲硅烷基)乙氧基]甲基]-1H-咪唑 在 三氟乙酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 1-(2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl)-2-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

文献信息

• 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
  作者：Tadashi Honda、Albena T. Dinkova-Kostova、Emilie David、Eric M. Padegimas、Chitra Sundararajan、Melean Visnick、Ron Bumeister、W. Christian Wigley

  DOI：10.1016/j.bmcl.2011.03.018

  日期：2011.4

  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.