methyl 3-fluoro-4-hydroxycinnamate | 1207954-10-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl 3-fluoro-4-hydroxycinnamate
• 英文别名: Methyl 3-(3-fluoro-4-hydroxyphenyl)prop-2-enoate；methyl 3-(3-fluoro-4-hydroxyphenyl)prop-2-enoate
• CAS: 1207954-10-6
• 化学式: C₁₀H₉FO₃
• 分子量: 196.178
• InChiKey: ANGCKEXOIZGQFH-UHFFFAOYSA-N

物化性质

• 沸点：
  289.0±25.0 °C(Predicted)
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-fluoro-4-hydroxycinnamate 在 水 、 potassium carbonate 、 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 2.5h， 生成 3'-fluoro-4'-isopentenyloxycinnamic acid
  参考文献：
  名称：

  Topical anti-inflammatory activity of boropinic acid and its natural and semi-synthetic derivatives

  摘要：

  Boropinic acid is a natural isopentenyloxycinnamic acid extracted from the aerial parts of Boronia pinnata Sm. (Rutaceae) with soybean 5-lipoxygenase inhibitory activity. In this paper the topical anti-inflammatory activity of boropinic acid and some of its natural and semi-synthetic derivatives was evaluated using the Croton oil ear test in mice as a model of acute inflammation. Some of the tested compounds (15, 17, 19, 20) revealed an effect comparable (ID50 = 0.18 divided by 0.72 mu mol/cm(2)) to that of the reference drug indomethacin (ID50 = 0.23 mu mol/cm(2)), a non-steroidal anti-inflammatory drug. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.107
• 作为产物：
  描述：

  2-氟苯酚 在 乌洛托品 、 sodium 作用下， 以 甲醇 为溶剂， 反应 36.0h， 生成 methyl 3-fluoro-4-hydroxycinnamate
  参考文献：
  名称：

  Topical anti-inflammatory activity of boropinic acid and its natural and semi-synthetic derivatives

  摘要：

  Boropinic acid is a natural isopentenyloxycinnamic acid extracted from the aerial parts of Boronia pinnata Sm. (Rutaceae) with soybean 5-lipoxygenase inhibitory activity. In this paper the topical anti-inflammatory activity of boropinic acid and some of its natural and semi-synthetic derivatives was evaluated using the Croton oil ear test in mice as a model of acute inflammation. Some of the tested compounds (15, 17, 19, 20) revealed an effect comparable (ID50 = 0.18 divided by 0.72 mu mol/cm(2)) to that of the reference drug indomethacin (ID50 = 0.23 mu mol/cm(2)), a non-steroidal anti-inflammatory drug. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.107

文献信息

• Synthesis and structure–activity relationship of novel lactam-fused chroman derivatives having dual affinity at the 5-HT1A receptor and the serotonin transporter
  作者：Zhongqi Shen、P. Siva Ramamoorthy、Nicole T. Hatzenbuhler、Deborah A. Evrard、Wayne Childers、Boyd L. Harrison、Michael Chlenov、Geoffrey Hornby、Deborah L. Smith、Kelly M. Sullivan、Lee E. Schechter、Terrance H. Andree

  DOI：10.1016/j.bmcl.2009.10.134

  日期：2010.1

  The structure–activity relationship (SAR) for three series of lactam-fused chroman derivatives possessing 3-amino substituents was evaluated. Many compounds exhibited affinities for both the 5-HT1A receptor and the 5-HT transporter. Compounds 45 and 53 demonstrated 5-HT1A antagonist activities in the in vitro cAMP turnover model.

  评估了具有3-氨基取代基的三个系列内酰胺融合的苯并二氢吡喃衍生物的结构-活性关系（SAR）。许多化合物对5-HT 1A受体和5-HT转运蛋白都表现出亲和力。化合物45和53在体外cAMP转换模型中显示了5-HT 1A拮抗剂活性。