3-hydroxy-4-methoxy-N-propylbenzamide | 216374-54-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-hydroxy-4-methoxy-N-propylbenzamide
• CAS: 216374-54-8
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: PJVCJKVVRZIDKC-UHFFFAOYSA-N

物化性质

• 熔点：
  110-112 °C
• 沸点：
  357.2±32.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-4-methoxy-N-propylbenzamide 在 sodium hydroxide 、 四(三苯基膦)钯 、 正丁基锂 、 adogen 464 、 二甲基硫 、 碘 、 铜 、 臭氧 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.5h， 生成 3,8-dimethoxy-1-(2-oxoethyl)[1]benzopyrano[5,4,3-cde][1]benzopyran-5,10-dione
  参考文献：
  名称：

  Total Synthesis of Taspine

  摘要：

  DOI：

  10.1021/jo981099j
• 作为产物：
  描述：

  正丙胺 、 3-羟基-4-甲氧基苯甲酸 在 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 作用下， 生成 3-hydroxy-4-methoxy-N-propylbenzamide
  参考文献：
  名称：

  Total Synthesis of Taspine

  摘要：

  DOI：

  10.1021/jo981099j

文献信息

• Aryl amide small-molecule inhibitors of microRNA miR-21 function
  作者：Yuta Naro、Meryl Thomas、Matthew D. Stephens、Colleen M. Connelly、Alexander Deiters

  DOI：10.1016/j.bmcl.2015.07.016

  日期：2015.11

  MicroRNAs (miRNAs) are single stranded RNA molecules of similar to 22 nucleotides that negatively regulate gene expression. MiRNAs are involved in fundamental cellular processes, such as development, differentiation, proliferation, and survival. MiRNA misregulation has been linked to various human diseases, most notably cancer. MicroRNA-21 (miR-21), a well-established oncomiR, is significantly overexpressed in many types of human cancers, thus rendering miR-21 a potential therapeutic target. Using a luciferase-based reporter assay under the control of miR-21 expression, a high-throughput screen of >300,000 compounds led to the discovery of a new aryl amide class of small-molecule miR-21 inhibitors. Structure-activity relationship (SAR) studies resulted in the development of four aryl amide derivatives as potent and selective miR-21 inhibitors. The intracellular levels of various miRNAs in HeLa cells were analyzed by qRT-PCR revealing specificity for miR-21 inhibition over other miRNAs. Additionally, preliminary mechanism of action studies propose a different mode of action compared to previously reported miR-21 inhibitors, thus affording a new chemical probe for future studies. (C) 2015 Elsevier Ltd. All rights reserved.
• Total Synthesis of Taspine
  作者：T. Ross Kelly、Roger L. Xie

  DOI：10.1021/jo981099j

  日期：1998.10.1