methyl 3-chloro-4-hydroxycinnamate | 185527-66-6

• 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-chloro-4-hydroxycinnamate
• 英文别名: Methyl 3-(3-chloro-4-hydroxyphenyl)prop-2-enoate；methyl 3-(3-chloro-4-hydroxyphenyl)prop-2-enoate
• CAS: 185527-66-6
• 化学式: C₁₀H₉ClO₃
• 分子量: 212.633
• InChiKey: BZHVHNVZOHIELV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-chloro-4-hydroxycinnamate 在 水 、 potassium carbonate 、 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 2.5h， 生成 3'-chloro-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：

  对羟基苯甲醛 在 N-氯代丁二酰亚胺 、 sodium 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 26.0h， 生成 methyl 3-chloro-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

• Inhibition of COX-1 activity and COX-2 expression by 3-(4′-geranyloxy-3′-methoxyphenyl)-2-trans propenoic acid and its semi-synthetic derivatives
  作者：Salvatore Genovese、Massimo Curini、Paolo Gresele、Teresa Corazzi、Francesco Epifano

  DOI：10.1016/j.bmcl.2011.07.040

  日期：2011.10

  Oxyprenylated naturally occurring cinnamic acids displayed efficient and promising biological activities. Aim of this study was to characterize the effects of 3-(4'-geranyl-3'-methoxy) phenyl-2-trans propenoic acid and its selected semi-synthetic analogues, on COX-2 expression and activity, and on COX-1 activity, in purified systems or in whole cell systems. The anti-inflammatory activity of title compounds (1) was tested as inhibition of COX-2 on isolated monocytes stimulated with LPS (10 mu g/ml). COX-2 expression was completely suppressed when monocytes were incubated with 100 mu M of 3-(4'-geranyl-3'-methoxy)phenyl-2-trans propenoic acid (1) or 3-(4'-isopentenyloxy) phenyl-2-trans propenoic acid (4). Moreover compounds (1) and (4) inhibit dose-dependently LPS-induced COX-2 expression. (c) 2011 Elsevier Ltd. All rights reserved.
• Topical anti-inflammatory activity of boropinic acid and its natural and semi-synthetic derivatives
  作者：Francesco Epifano、Silvio Sosa、Aurelia Tubaro、M. Carla Marcotullio、Massimo Curini、Salvatore Genovese

  DOI：10.1016/j.bmcl.2010.11.107

  日期：2011.1

  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.