allyl 3-(3,4-dimethoxyphenyl)-2-hydroxypropanoate | 1322088-10-7

• 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: allyl 3-(3,4-dimethoxyphenyl)-2-hydroxypropanoate
• 英文别名: Prop-2-enyl 3-(3,4-dimethoxyphenyl)-2-hydroxypropanoate
• CAS: 1322088-10-7
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: GEZBVUAGXJFFFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  allyl 3-(3,4-dimethoxyphenyl)-2-hydroxypropanoate 在 吗啉 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 碘代三甲硅烷 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 喹啉 、 二氯甲烷 为溶剂， 反应 28.5h， 生成 rosmarinic acid
  参考文献：
  名称：

  Synthesis of derivatives of methyl rosmarinate and their inhibitory activities against matrix metalloproteinase-1 (MMP-1)

  摘要：

  A series of MMP-1 inhibitors have been identified based upon a methyl rosmarinate scaffold using structure-based drug design methods. The best compound in the series showed an IC50 value of 0.4 mu M. A docking study was conducted for compound (S)-10n in order to investigate its binding interactions with MMP-1. The structure activity relationships (SAR) were also briefly discussed. Useful SAR was established which provides important guidelines for the design of future generations of potent inhibitors against MMP-1. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.047
• 作为产物：
  描述：

  (Z)-3-(3,4-dimethoxyphenyl)-2-hydroxyacrylic acid 在 sodium tetrahydroborate 、 对甲苯磺酸 、 sodium hydroxide 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 10.0h， 生成 allyl 3-(3,4-dimethoxyphenyl)-2-hydroxypropanoate
  参考文献：
  名称：

  Synthesis of derivatives of methyl rosmarinate and their inhibitory activities against matrix metalloproteinase-1 (MMP-1)

  摘要：

  A series of MMP-1 inhibitors have been identified based upon a methyl rosmarinate scaffold using structure-based drug design methods. The best compound in the series showed an IC50 value of 0.4 mu M. A docking study was conducted for compound (S)-10n in order to investigate its binding interactions with MMP-1. The structure activity relationships (SAR) were also briefly discussed. Useful SAR was established which provides important guidelines for the design of future generations of potent inhibitors against MMP-1. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.047

文献信息

• ＴＲＰＶ４活性抑制剤
  申请人：花王株式会社

  公开号：JP2020059675A

  公开（公告）日：2020-04-16

  【課題】ＴＲＰＶ４の活性を抑制し、過活動膀胱や過敏性腸症候群等の予防又は改善に有用な化合物の提供。【解決手段】下式（Ｉａ）〜（Ｉｄ）から選ばれるロズマリン酸誘導体又はその塩を有効成分とするＴＲＰＶ４活性抑制剤。【選択図】なし

  提供抑制TRPV4活性的化合物，用于预防或改善过度活动膀胱或过敏性肠综合征等。选取自下式（Ia）至（Id）的迷迭香酸衍生物或其盐作为有效成分的TRPV4活性抑制剂。【选择图】无
• Sustainable Synthesis of α‐Hydroxycarboxylic Acids by Manganese Catalyzed Acceptorless Dehydrogenative Coupling of Ethylene Glycol and Primary Alcohols**
  作者：Satyadeep Waiba、Kakoli Maji、Mamata Maiti、Biplab Maji

  DOI：10.1002/anie.202218329

  日期：2023.3

  A versatile synthesis of highly demanded α-hydroxycarboxylic acids via dehydrogenative coupling of two feedstock chemicals, ethylene glycol, and primary alcohols, is reported. An Earth's abundant metal complex catalyzes the reaction with high yields and selectivities. Water and hydrogen gas are produced as the sole byproducts.

  报道了通过两种原料化学品、乙二醇和伯醇的脱氢偶联来合成高度需求的 α-羟基羧酸。地球上丰富的金属络合物以高产率和选择性催化反应。水和氢气是唯一的副产品。
• Synthesis of derivatives of methyl rosmarinate and their inhibitory activities against matrix metalloproteinase-1 (MMP-1)
  作者：Hu Yuan、Weiqiang Lu、Liyan Wang、Lei Shan、Honglin Li、Jin Huang、Qingyan Sun、Weidong Zhang

  DOI：10.1016/j.ejmech.2012.09.047

  日期：2013.4

  A series of MMP-1 inhibitors have been identified based upon a methyl rosmarinate scaffold using structure-based drug design methods. The best compound in the series showed an IC50 value of 0.4 mu M. A docking study was conducted for compound (S)-10n in order to investigate its binding interactions with MMP-1. The structure activity relationships (SAR) were also briefly discussed. Useful SAR was established which provides important guidelines for the design of future generations of potent inhibitors against MMP-1. (C) 2012 Elsevier Masson SAS. All rights reserved.