methyl 5-hydroxy-4-methoxy-2-prenylbenzoate | 1060689-23-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 5-hydroxy-4-methoxy-2-prenylbenzoate
• 英文别名: methyl 5-hydroxy-4-methoxy-2-(3-methylbut-2-enyl)benzoate
• CAS: 1060689-23-7
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: OBRDAQJUCPIGEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5-hydroxy-4-methoxy-2-prenylbenzoate 在 四氧化锇 、 sodium periodate 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 反应 12.5h， 以41.9%的产率得到methyl 2-(2-oxoethyl)-5-hydroxy-4-methoxybenzoate
  参考文献：
  名称：

  噻吩啉及其类似物的高效合成

  摘要：

  摘要 以3-羟基-4-甲氧基苯甲酸甲酯为原料，通过异戊二烯醚化、克莱森重排、氧化、亚胺形成、还原胺化和分子内酰胺化合成了Thalifoline (1)及其类似物。最后三个步骤，亚胺形成、还原胺化和分子内酰胺化，在室温下在一锅中完成。

  DOI：

  10.1080/00397910802590894
• 作为产物：
  描述：

  Methyl 4-methoxy-3-(3-methylbut-2-enoxy)benzoate 在 N,N-二甲基苯胺 作用下， 反应 8.0h， 以75%的产率得到methyl 5-hydroxy-4-methoxy-2-prenylbenzoate
  参考文献：
  名称：

  噻吩啉及其类似物的高效合成

  摘要：

  摘要 以3-羟基-4-甲氧基苯甲酸甲酯为原料，通过异戊二烯醚化、克莱森重排、氧化、亚胺形成、还原胺化和分子内酰胺化合成了Thalifoline (1)及其类似物。最后三个步骤，亚胺形成、还原胺化和分子内酰胺化，在室温下在一锅中完成。

  DOI：

  10.1080/00397910802590894

文献信息

• Synthesis and preliminary biological evaluation of novel taspine derivatives as anticancer agents
  作者：Jie Zhang、Yanmin Zhang、Yuanyuan Shan、Na Li、Wei Ma、Langchong He

  DOI：10.1016/j.ejmech.2010.03.001

  日期：2010.7

  Antiangiogenic therapy might represent a new promising anticancer therapeutic strategy. Taspine can significantly inhibit cell proliferation of human umbilical vein endothelial cells (HUVECs) induced by vascular endothelial growth factor-165, which is crucial for angiogenesis. In this study, a series of novel taspine derivatives were synthesized and screened for in vitro anticancer and antiangiogenesis activities. The majority of the derivatives demonstrated a moderate degree of cytotoxicity against human cancer cell lines. One of them (14) exhibited much better antiproliferative activity against CACO-2 (IC(50) = 52.5 mu M) and ECV304 (IC(50) = 2.67 mu M) cells than taspine did. Some of them were also effective in antiproliferative assays against HUVECs. The in silico estimate of solubility of title compounds were higher than that of taspine. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Discovery of novel taspine derivatives as antiangiogenic agents
  作者：Jie Zhang、Yanmin Zhang、Sanqi Zhang、Sicen Wang、Langchong He

  DOI：10.1016/j.bmcl.2009.11.073

  日期：2010.1

  VEGFR-2 plays a critical role in vasculogenesis and inhibitors of VEGFR-2 could be used in the treatment of cancer. Taspine was one of the active ingredients screened by using an endothelial cell membrane chromatography and showed inhibition against VEGFR-2. In our research, we explored how the lactone ring and biphenyl scaffold in taspine influence its potent in vitro anticancer and antiangiogenesis activities. Accordingly, we report the design, synthesis, and preliminary evaluation of four novel taspine derivatives as VEGFR-2 inhibitors. The preliminary biological test showed that one of the compounds showed much better inhibitory activities against CACO-2 (IC50 = 52.5 nM) and ECV304 (IC50 = 2.67 nM) than taspine. This result enlarges the interest in ring-opened taspine derivative skeleton in the search of new antiangiogenesis agents. (C) 2009 Elsevier Ltd. All rights reserved.