methyl E-3-(4-hydroxy-3-formylphenyl)acrylate | 417712-26-6

• 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 E-3-(4-hydroxy-3-formylphenyl)acrylate
• 英文别名: methyl psilalate；methyl (E)-3-(3-formyl-4-hydroxyphenyl)acrylate；methyl (3-formyl-4-hydroxy)cinnamate；methyl (2E)-3-(3-formyl-4-hydroxyphenyl)acrylate；methyl (E)-3-(3-formyl-4-hydroxyphenyl)prop-2-enoate
• CAS: 417712-26-6
• 化学式: C₁₁H₁₀O₄
• 分子量: 206.198
• InChiKey: YZCNMNIEOSATKG-HWKANZROSA-N

物化性质

• 熔点：
  100-101 °C
• 沸点：
  331.8±32.0 °C(Predicted)
• 密度：
  1.284±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 储存条件：
  存储条件：2-8°C，氮气保护保存。

反应信息

• 作为反应物：
  描述：

  methyl E-3-(4-hydroxy-3-formylphenyl)acrylate 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 lithium hydroxide 、 potassium acetate 、 三乙胺 、 联硼酸频那醇酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 (E)-3-[4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-formylphenyl]prop-2-enoic acid
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of a New Series of Retinoid-Related Biphenyl-4-ylacrylic Acids Endowed with Antiproliferative and Proapoptotic Activity

  摘要：

  Atypical retinoids (AR) represent a class of proapoptotic agents with promising potential in the treatment of neoplastic diseases. In the present work 4'-hydroxybiphenyl-4-ylacrylic acids were studied as a novel series of AR. The synthesized compounds were evaluated for their antiproliferative activity in a human promyelocytic leukemia cell line (NB4) and in an ovarian carcinoma cell system including IGROV-1, carrying a functional wild-type p53, and a cisplatin-resistant subline, IGROV-1/Pt-1. The presence of a bulky lipophilic group at position 3' (adamantan-1-yl being the best) and the E configuration of the acrylic moiety appear essential for activity below 1 mu M. No substitution on the rings or on the double bond improved the activity. A qualitative correlation between the log P and molecular volume of the 3'-substituent and the antiproliferative activity was found. From the study of a few selected compounds, it appears that the presence of the carboxylic group is an essential requirement for apoptogenic properties but not for antiproliferative activity, this being maintained in amide derivatives. On the other hand, compounds able to induce apoptosis produced a detectable level of genotoxic damage. This observation supports the hypothesis that the genotoxic stress is a critical event mediating apoptosis induction by compounds of this class. Among the compounds investigated, E-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)acrylic acid (2) was chosen for further investigation.

  DOI：

  10.1021/jm049440h
• 作为产物：
  描述：

  水杨醛 在 palladium diacetate 、 一氯化碘 、 溶剂黄146 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 乙腈 为溶剂， 生成 methyl E-3-(4-hydroxy-3-formylphenyl)acrylate
  参考文献：
  名称：

  羟基肉桂酸甲酯的二氟甲基生物等排体在非极性环境中的抗氧化特性。

  摘要：

  目的 许多天然抗氧化剂的药代动力学特性较差，这会影响其治疗用途。对于羟基肉桂酸 (HCA) 和其他酚类抗氧化剂，它们的主要缺点是它们的低亲脂性和快速代谢。由于其氢键供体和受体特性，二氟甲基可被视为“亲油性羟基”；这促使我们将其评估为酚羟基的生物等排替代物，以增加 HCA 的亲脂性。方法 合成了 6 种与咖啡酸相关的二氟甲基取代的肉桂酸甲酯（4a-c、5a-c），并通过化学（FRAP、DPPH 清除、β-胡萝卜素漂白抑制，1-200 μm）、电化学评价其抗氧化活性。 （差分脉冲伏安法，循环伏安法）和基于细胞的（抑制红细胞中的脂质过氧化，在 1 和 50 μm）测定。关键发现 类似物 4a-c 和 5a-c 在 FRAP 和 DPPH 测定中没有活性，并且只有那些含有游离酚羟基（4a 和 5a）的化合物表现出电化学活性，尽管具有高氧化还原电位。化合物 4a、b 和 5a、b 在抑制 β-胡萝卜

  DOI：

  10.1111/jphp.12507

文献信息

• Inhibitors of protein kinase for the treatment of disease
  申请人：——

  公开号：US20030187007A1

  公开（公告）日：2003-10-02

  The present invention is directed in part towards methods of modulating the function of protein kinases with phenol- and hydroxynaphthalene-based compounds. The methods incorporate cells that express a protein kinase. In addition, the invention describes methods of preventing and treating protein kinase-related abnormal conditions in organisms with a compound identified by the invention. Furthermore, the invention pertains to phenol- and hydroxynaphthalene-based compounds and pharmaceutical compositions comprising these compounds.

  本发明部分涉及使用基于酚和羟基萘的化合物调节蛋白激酶功能的方法。这些方法涉及表达蛋白激酶的细胞。此外，该发明描述了使用本发明鉴定的化合物预防和治疗生物体中与蛋白激酶相关的异常情况的方法。此外，该发明涉及基于酚和羟基萘的化合物以及包含这些化合物的药物组合物。
• Synthesis and structural characterization of a palladium complex as an anticancer agent, and a highly efficient and reusable catalyst for the Heck coupling reaction under ultrasound irradiation: A convenient sustainable green protocol
  作者：Mohamed M. El-bendary、Tamer S. Saleh、Abdullah S. Al-Bogami

  DOI：10.1016/j.poly.2020.114924

  日期：2021.1

  activities of the palladium complex 1 were studied with respect to human breast cancer (MCF-7) and hepatocellular carcinoma (HePG-2) cell lines. The data obtained show that complex 1 displays strong activity towards the viability and the growth of the cancer cell lines MCF-7 and HepG2. Additionally, complex 1 exhibits excellent catalytic activity for the Heck cross-coupling reaction with water as the

  摘要在环境条件下，通过氯化钯和吡啶-2-甲醛-肟（paOH）的自组装法合成了[Pd（paOH）2] .2Cl（1）配合物。配合物1通过FT-IR，UV-vis和NMR光谱技术以及元素分析得到了充分表征。配合物1的单晶X射线结构表明，Pd（II）离子与两个吡啶-2-甲醛-肟的两个配体键合到四个氮原子上。配合物1中的Pd（II）离子的分子几何结构呈正方形，具有反型几何结构和两个游离氯离子。使用MTT测定法，研究了钯复合物1对人乳腺癌（MCF-7）和肝细胞癌（HePG-2）细胞系的抗癌活性。获得的数据表明，复合物1显示出对癌细胞系MCF-7和HepG2的活力和生长的强活性。另外，在超声辐射下，配合物1对于以水为溶剂的Heck交叉偶联反应表现出优异的催化活性。超声辐射不仅提高了反应的速率和收率，而且促进了原位生成由络合物1形成的良好分散的零价Pd胶体作为活性催化剂。最后，对络合物1的发光光谱进行了讨论。
• Synthesis and Structure−Activity Relationships of a New Series of Retinoid-Related Biphenyl-4-ylacrylic Acids Endowed with Antiproliferative and Proapoptotic Activity
  作者：Raffaella Cincinelli、Sabrina Dallavalle、Raffaella Nannei、Serena Carella、Daniele De Zani、Lucio Merlini、Sergio Penco、Enrico Garattini、Giuseppe Giannini、Claudio Pisano、Loredana Vesci、Paolo Carminati、Valentina Zuco、Chiara Zanchi、Franco Zunino

  DOI：10.1021/jm049440h

  日期：2005.7.1

  Atypical retinoids (AR) represent a class of proapoptotic agents with promising potential in the treatment of neoplastic diseases. In the present work 4'-hydroxybiphenyl-4-ylacrylic acids were studied as a novel series of AR. The synthesized compounds were evaluated for their antiproliferative activity in a human promyelocytic leukemia cell line (NB4) and in an ovarian carcinoma cell system including IGROV-1, carrying a functional wild-type p53, and a cisplatin-resistant subline, IGROV-1/Pt-1. The presence of a bulky lipophilic group at position 3' (adamantan-1-yl being the best) and the E configuration of the acrylic moiety appear essential for activity below 1 mu M. No substitution on the rings or on the double bond improved the activity. A qualitative correlation between the log P and molecular volume of the 3'-substituent and the antiproliferative activity was found. From the study of a few selected compounds, it appears that the presence of the carboxylic group is an essential requirement for apoptogenic properties but not for antiproliferative activity, this being maintained in amide derivatives. On the other hand, compounds able to induce apoptosis produced a detectable level of genotoxic damage. This observation supports the hypothesis that the genotoxic stress is a critical event mediating apoptosis induction by compounds of this class. Among the compounds investigated, E-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)acrylic acid (2) was chosen for further investigation.
• Antioxidant properties in a non-polar environment of difluoromethyl bioisosteres of methyl hydroxycinnamates
  作者：Mario D Martínez、Lorena Luna、Alvaro Y Tesio、Gabriela E Feresin、Fernando J Durán、Gerardo Burton

  DOI：10.1111/jphp.12507

  日期：2016.2.16

  properties that impair their therapeutic use. For hydroxycinnamic acids (HCAs) and other phenolic antioxidants, their major drawback is their low lipophilicity and a rapid metabolism. The difluoromethyl group may be considered as a 'lipophilic hydroxyl' due to its hydrogen bond donor and acceptor properties; this prompted us to assess it as a bioisosteric replacement of a phenolic hydroxyl for increasing

  目的 许多天然抗氧化剂的药代动力学特性较差，这会影响其治疗用途。对于羟基肉桂酸 (HCA) 和其他酚类抗氧化剂，它们的主要缺点是它们的低亲脂性和快速代谢。由于其氢键供体和受体特性，二氟甲基可被视为“亲油性羟基”；这促使我们将其评估为酚羟基的生物等排替代物，以增加 HCA 的亲脂性。方法 合成了 6 种与咖啡酸相关的二氟甲基取代的肉桂酸甲酯（4a-c、5a-c），并通过化学（FRAP、DPPH 清除、β-胡萝卜素漂白抑制，1-200 μm）、电化学评价其抗氧化活性。 （差分脉冲伏安法，循环伏安法）和基于细胞的（抑制红细胞中的脂质过氧化，在 1 和 50 μm）测定。关键发现 类似物 4a-c 和 5a-c 在 FRAP 和 DPPH 测定中没有活性，并且只有那些含有游离酚羟基（4a 和 5a）的化合物表现出电化学活性，尽管具有高氧化还原电位。化合物 4a、b 和 5a、b 在抑制 β-胡萝卜