2-propoxyimino-3-phenylpropionic acid | 851769-60-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2-propoxyimino-3-phenylpropionic acid
• 英文别名: 3-Phenyl-2-propoxyiminopropanoic acid；3-phenyl-2-propoxyiminopropanoic acid
• CAS: 851769-60-3
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: UMIBCXINWMMONC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-propoxyimino-3-phenylpropionic acid 在 4-二甲氨基吡啶 、 磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 14.0h， 生成 2-(2-O-propyloxymino-3-phenyl)propionyl 1-O-acetylbritannilactone ester
  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 sodium hydroxide 、 亚硝酸乙酯 、 sodium ethanolate 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 7.0h， 生成 2-propoxyimino-3-phenylpropionic acid
  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

• Design, Synthesis, and Antitumor Activity of Novel Acylate of 6-OH at 1- O-acetylbritannilactone
  作者：Shouxin Liu、Jun Feng、He Liu、Junzhang Li、Xia Tian

  DOI：10.2174/1573406410666140815123216

  日期：2015.1.30

  N-(α-Alkyloxime-3-phenylpropionyl) proline was designed and synthesized as an acylating agent to modify the 6-OH of 1-O-acetylbritannilactone. Eight intermediates and eight target compounds were obtained. The structures of sixteen novel compounds were characterized by 1HNMR, IR and HRMS. The activities against HL-60 and Bel-7402 cell lines were tested, the IC50 values of compound IVg were 2.7 μM and 4.3 μM, respectively.

  设计并合成了 N-(α-烷氧基肟-3-苯基丙酰基)脯氨酸作为酰化剂，用于修饰 1-O-acetylbritannilactone 的 6-OH。共得到 8 个中间体和 8 个目标化合物。通过 1HNMR、IR 和 HRMS 对 16 种新型化合物的结构进行了表征。测试了化合物 IVg 对 HL-60 和 Bel-7402 细胞株的活性，其 IC50 值分别为 2.7 μM 和 4.3 μM。
• Design, synthesis, and anti-tumor activity of (2-O-alkyloxime-3-phenyl)-propionyl-1-O-acetylbritannilactone esters
  作者：Shouxin Liu、He Liu、Weiying Yan、Li Zhang、Naisheng Bai、Chi-Tang Ho

  DOI：10.1016/j.bmc.2005.02.024

  日期：2005.4

  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.