3-(3,4-二羟基苯基)-2-甲氧基丙-2-烯酸 | 61854-88-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(3,4-二羟基苯基)-2-甲氧基丙-2-烯酸
• 英文名称: 3,4-Dihydroxy-α-methoxyzimtsaeure
• 英文别名: 3-(3,4-Dihydroxyphenyl)-2-methoxyprop-2-enoic acid
• CAS: 61854-88-4
• 化学式: C₁₀H₁₀O₅
• 分子量: 210.186
• InChiKey: HKSNOPIYKSDTOO-UHFFFAOYSA-N

物化性质

• 沸点：
  424.9±45.0 °C(Predicted)
• 密度：
  1.453±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 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：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(3,4-二羟基苯基)-2-甲氧基丙-2-烯酸 、 章胺盐酸盐 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 生成
  参考文献：
  名称：

  Synthesis and structure–activity relationship of botryllamides that block the ABCG2 multidrug transporter

  摘要：

  In previous work, botryllamides discovered from the marine ascidian Botryllus tyreus were characterized as selective inhibitors of the ABCG2 multidrug transporter. However, the structural basis for this activity could not be established. In this study, botryllamide F, the core botryllamide structure, and botryllamide G, the most potent botryllamide ABCG2 inhibitor, were synthesized along with a series of structural variants for evaluation of structure - activity relationships. The biological activity of synthetic botryllamide analogs implied that the 2-methoxy-p-coumaric acid portion, and the degree of double bond conjugation within this group, were critical for inhibition of ABCG2. However, variations in the substituents on the two aryl groups did not appear to significantly impact the potency or degree of inhibition. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.016
• 作为产物：
  描述：

  甲氧基乙酸甲酯 、 3,4-二羟基苯甲醛 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 3-(3,4-二羟基苯基)-2-甲氧基丙-2-烯酸
  参考文献：
  名称：

  Synthesis and structure–activity relationship of botryllamides that block the ABCG2 multidrug transporter

  摘要：

  In previous work, botryllamides discovered from the marine ascidian Botryllus tyreus were characterized as selective inhibitors of the ABCG2 multidrug transporter. However, the structural basis for this activity could not be established. In this study, botryllamide F, the core botryllamide structure, and botryllamide G, the most potent botryllamide ABCG2 inhibitor, were synthesized along with a series of structural variants for evaluation of structure - activity relationships. The biological activity of synthetic botryllamide analogs implied that the 2-methoxy-p-coumaric acid portion, and the degree of double bond conjugation within this group, were critical for inhibition of ABCG2. However, variations in the substituents on the two aryl groups did not appear to significantly impact the potency or degree of inhibition. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.016

文献信息

• Synthesis and structure–activity relationship of botryllamides that block the ABCG2 multidrug transporter
  作者：Kentaro Takada、Nobutaka Imamura、Kirk R. Gustafson、Curtis J. Henrich

  DOI：10.1016/j.bmcl.2010.01.016

  日期：2010.2

  In previous work, botryllamides discovered from the marine ascidian Botryllus tyreus were characterized as selective inhibitors of the ABCG2 multidrug transporter. However, the structural basis for this activity could not be established. In this study, botryllamide F, the core botryllamide structure, and botryllamide G, the most potent botryllamide ABCG2 inhibitor, were synthesized along with a series of structural variants for evaluation of structure - activity relationships. The biological activity of synthetic botryllamide analogs implied that the 2-methoxy-p-coumaric acid portion, and the degree of double bond conjugation within this group, were critical for inhibition of ABCG2. However, variations in the substituents on the two aryl groups did not appear to significantly impact the potency or degree of inhibition. (C) 2010 Elsevier Ltd. All rights reserved.