ethyl 2-cyclohexyloxyimine-3-phenylpropionate | 851769-59-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 2-cyclohexyloxyimine-3-phenylpropionate
• 英文别名: ethyl 2-cyclohexyloxyimino-3-phenylpropionate
• CAS: 851769-59-0
• 化学式: C₁₇H₂₃NO₃
• 分子量: 289.375
• InChiKey: FEKDPLDTJCQHBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  47.89
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-cyclohexyloxyimine-3-phenylpropionate 在 sodium hydroxide 、 磺酰氯 作用下， 以 乙醇 、 苯 为溶剂， 反应 5.0h， 生成 2-[(Z)-Cyclohexyloxyimino]-3-phenyl-propionyl chloride
  参考文献：
  名称：

  Design, synthesis, and anti-tumor activity of (2-O-alkyloxime-3-phenyl)-propionyl-1-O-acetylbritannilactone esters

  摘要：

  The extracts of Inula britannica have anti-inflammatory, anti-bacterial, anti-hepatitic, and anti-tumor activities. Various sesquiterpene lactones with cytotoxic properties including 1-O-acetylbritannilactone (1) have been isolated from this Chinese medicinal plant. Eight derivatives of 1-O-acetylbritannilactone, (2-O-alkyloxime-3-phenyl)-propionyt-1-O-acetylbritannilactone esters were designed and synthesized. Four of these compounds were tested to show inhibitory activity on the growth of human leukemia HL-60 and cancer Bel-7402 cell lines. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.024
• 作为产物：
  描述：

  2-苄基乙酰乙酸乙酯 在 亚硝酸乙酯 、 sodium ethanolate 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 4.0h， 生成 ethyl 2-cyclohexyloxyimine-3-phenylpropionate
  参考文献：
  名称：

  Design, synthesis, and anti-tumor activity of (2-O-alkyloxime-3-phenyl)-propionyl-1-O-acetylbritannilactone esters

  摘要：

  The extracts of Inula britannica have anti-inflammatory, anti-bacterial, anti-hepatitic, and anti-tumor activities. Various sesquiterpene lactones with cytotoxic properties including 1-O-acetylbritannilactone (1) have been isolated from this Chinese medicinal plant. Eight derivatives of 1-O-acetylbritannilactone, (2-O-alkyloxime-3-phenyl)-propionyt-1-O-acetylbritannilactone esters were designed and synthesized. Four of these compounds were tested to show inhibitory activity on the growth of human leukemia HL-60 and cancer Bel-7402 cell lines. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.024

文献信息

• Synthesis and activity evaluation of the cyclic dipeptides arylidene N -alkoxydiketopiperazines
  作者：Xia Tian、Juan Feng、Shi-ming Fan、Xiao-li zhen、Jian-rong Han、Shou-xin Liu

  DOI：10.1016/j.bmc.2016.08.038

  日期：2016.11

  intramolecular acylation. Possible cyclization and acid-catalyzed rearrangement-fragmentation mechanisms were discussed. The crystal structure of the novel diketopiperazine further confirmed the rearrangement mechanism. Most compounds exhibited antitumor activity. Several compounds were more potent against caspase-3. Specifically, compounds 6e, 6g, and 6f inhibited caspase-3 at IC50 values lying within the

  设计了一系列芳基N-烷氧基二酮哌嗪并通过肟醚形成和分子内酰化立体合成。讨论了可能的环化和酸催化的重排-断裂机理。新型二酮哌嗪的晶体结构进一步证实了重排机理。大多数化合物表现出抗肿瘤活性。几种化合物对caspase-3更有效。具体而言，化合物6e，6g和6f在IC 50上抑制caspase-3值在低微摩尔范围内，并显示出良好的选择性。基于分子对接的结果，还讨论了烷氧基二酮哌嗪在caspase-3活性中心的结合方式。
• Stereoselective synthesis and rearrangement-fragmentation of arylidene N-alkoxydiketopiperazines
  作者：Shouxin Liu、Yun Mu、Jianrong Han、Xiaoli Zhen、Yihua Yang、Xia Tian、Andrew Whiting

  DOI：10.1039/c1ob05722g

  日期：——

  A stereoselective synthesis of arylidene N-alkoxydiketopiperazines viaoxime-ether formation and intramolecular acylation is described, followed by an acid-catalysed rearrangement-fragmentation to give novel diketopiperazine hemiaminal derivatives with useful bioactivity against certain tumour cell lines.

  描述了通过肟-醚形成和分子内酰化立体选择性合成芳基N-烷氧基二酮哌嗪类化合物，然后进行酸催化的重排-片段化反应，从而得到新颖的二酮哌嗪类半胱氨酸衍生物，其对某些肿瘤细胞系具有有用的生物活性。