(E)-2-methyl-3-(4-(cyclohex-1-en-1-yl)furan-2-yl)acrylamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (E)-2-methyl-3-(4-(cyclohex-1-en-1-yl)furan-2-yl)acrylamide
• 英文别名: (E)-3-[4-(cyclohexen-1-yl)furan-2-yl]-2-methylprop-2-enamide
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: PKSXKSHZCUMXBC-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  56.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-溴-2-呋喃甲醛 在 哌啶 、 吡啶 、 ammonium hydroxide 、 氯化亚砜 、 caesium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.08h， 生成 (E)-2-methyl-3-(4-(cyclohex-1-en-1-yl)furan-2-yl)acrylamide
  参考文献：
  名称：

  Design and synthesis of natural product derivatives with selective and improved cytotoxicity based on a sesquiterpene scaffold

  摘要：

  Brasilamide E (1) is a bisabolane sesquiterpenoid isolated from the solid-substrate fermentation cultures of a plant endophytic fungus Paraconiothyrium brasiliense. The compound specifically inhibited proliferation of the MCF-7 cells, but did not show cytotoxicity towards the negative controls HaCaT and NIH3T3 cells (IC50 > 50 mu M). To improve its potency while maintain selectivity, a total of 27 derivatives of 1 were designed, synthesized, and evaluated for in vitro cytotoxicity against six tumor cell lines and the negative control NIH3T3 cells. Among these compounds, compound 12b showed significantly improved potency against the MCF-7, HeLa, and HO8910 cells with IC50 values of 0.13-0.25 mu M compared to 1 (IC50 8.47-18.00 mu M), and remained nontoxic to the NIH3T3 cells. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.03.022

文献信息

• Design and synthesis of natural product derivatives with selective and improved cytotoxicity based on a sesquiterpene scaffold
  作者：Yang Zhang、Zhuowei Zhang、Bo Wang、Ling Liu、Yongsheng Che

  DOI：10.1016/j.bmcl.2016.03.022

  日期：2016.4

  Brasilamide E (1) is a bisabolane sesquiterpenoid isolated from the solid-substrate fermentation cultures of a plant endophytic fungus Paraconiothyrium brasiliense. The compound specifically inhibited proliferation of the MCF-7 cells, but did not show cytotoxicity towards the negative controls HaCaT and NIH3T3 cells (IC50 > 50 mu M). To improve its potency while maintain selectivity, a total of 27 derivatives of 1 were designed, synthesized, and evaluated for in vitro cytotoxicity against six tumor cell lines and the negative control NIH3T3 cells. Among these compounds, compound 12b showed significantly improved potency against the MCF-7, HeLa, and HO8910 cells with IC50 values of 0.13-0.25 mu M compared to 1 (IC50 8.47-18.00 mu M), and remained nontoxic to the NIH3T3 cells. (C) 2016 Elsevier Ltd. All rights reserved.