3-(3,4-dimethoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide

• 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: 3-(3,4-dimethoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide
• 化学式: C₁₉H₂₁NO₄
• 分子量: 327.38
• InChiKey: OKMGPBABYTWQIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3,4-dimethoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide 在 碘苯二乙酸 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Isolation and Synthesis of Melodamide A, a New Anti-inflammatory Phenolic Amide from the Leaves of Melodorum fruticosum

  摘要：

  Together with twelve known compounds (2-13), melodamide A (1), a new phenolic amide possessing p-quinol moiety, was purified and characterized from the methanolic extracts of the leaves of Melodorum fruticosum. The structure of melodamide A (1) was established with a combination of 2D NMR experiments, HR-ESI-MS and X-ray analyses. The other known compounds were identified by comparison of their spectroscopic and physical data with those reported in the literature. Moreover, some isolated compounds were examined for their inhibitory activity towards superoxide anion generation and elastase release in human neutrophils. Among the tested compounds, 1, 3, and 5 exhibited strong inhibition of superoxide anion generation with IC50 values ranging from 5.25 to 8.65 mu M. Furthermore, synthesis and biological evaluation of melodamide A (1) and its analogs (14a-p) were described.

  DOI：

  10.1055/s-0032-1328131
• 作为产物：
  描述：

  对羟基苯乙胺 、 3,4-dimethoxy-cinnamoyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 3-(3,4-dimethoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide
  参考文献：
  名称：

  Isolation and Synthesis of Melodamide A, a New Anti-inflammatory Phenolic Amide from the Leaves of Melodorum fruticosum

  摘要：

  Together with twelve known compounds (2-13), melodamide A (1), a new phenolic amide possessing p-quinol moiety, was purified and characterized from the methanolic extracts of the leaves of Melodorum fruticosum. The structure of melodamide A (1) was established with a combination of 2D NMR experiments, HR-ESI-MS and X-ray analyses. The other known compounds were identified by comparison of their spectroscopic and physical data with those reported in the literature. Moreover, some isolated compounds were examined for their inhibitory activity towards superoxide anion generation and elastase release in human neutrophils. Among the tested compounds, 1, 3, and 5 exhibited strong inhibition of superoxide anion generation with IC50 values ranging from 5.25 to 8.65 mu M. Furthermore, synthesis and biological evaluation of melodamide A (1) and its analogs (14a-p) were described.

  DOI：

  10.1055/s-0032-1328131

文献信息

• Verfahren zur enzymatischen Herstellung von 3,4-O-dimethylierten Zimtsäuren, 3,4-Dimethoxyphenethylaminen und 4-O-methylierten Zimtsäureamiden
  申请人：Symrise AG

  公开号：EP3050971A1

  公开（公告）日：2016-08-03

  Die Erfindung betrifft die Bereitstellung von sowohl fermentativen als auch biotechnologischen Verfahren zur Herstellung von 3,4-methylierten Zimtsäuren, 3,4-methylierten Zimtsäureestern, 3,4-Dimethoxyphenethylamin und 4-methylierten Zimtsäureamiden unter Verwendung einer 4'-O-Methyltransferase ggf. in Kombination mit weiteren Enzymen, wobei die Enzyme mittels metabolic engineering ausgewählt und ggf. durch gezielte Optimierung angepasst wurden sowie Zusammensetzungen, welche durch die Verfahren erhalten werden. Weiter betrifft die Erfindung Vektorsysteme, rekombinante Mikroorganismen oder Pilze, sowie spezifische Nukleinsäure-Abschnitte und Polypeptide.

  本发明涉及使用 4'-O-甲基转移酶（可选择与其他酶结合使用，这些酶通过代谢工程选择，可选择通过特定优化进行调整）生产 3,4-甲 基肉桂酸、3,4-甲基肉桂酸酯、3,4-二甲氧基苯乙胺和 4-甲基肉桂酸酰胺的发酵和生物技术工艺，以及通过该工艺获得的组合物。 本发明还涉及载体系统、重组微生物或真菌，以及特定的核酸部分和多肽。
• Method for biotechnological production of methylized cinnamic acids and cinnamic acid esters, methylized phenethylamines and the coupling products thereof, particularly of cinnamic acid amides
  申请人：SYMRISE AG

  公开号：US10227620B2

  公开（公告）日：2019-03-12

  The invention relates to providing both fermentative and biotechnological methods for producing 3,4-methylized cinnamic acids, 3,4-methylized cinnamic acid esters, 3,4-dimethoxyphenethylamine, and 4-methylized cinnamic acid amides using a 4′-O-methyltransferase, optionally in combination with further enzymes, wherein the enzymes are selected by means of metabolic engineering and operation have been adapted by targeted optimization, and compositions obtained by means of the method. The invention further relates to vector systems, recombinant microorganisms or fungi, and specific nucleic acid segments and polypeptides.

  本发明涉及提供利用 4′-O-甲基转移酶（可选择与其他酶结合）生产 3,4-甲基化肉桂酸、3,4-甲基化肉桂酸酯、3,4-二甲氧基苯乙胺和 4-甲基化肉桂酸酰胺的发酵和生物技术方法，其中酶是通过代谢工程方法选择的，操作是通过定向优化调整的，以及通过该方法获得的组合物。 本发明还涉及载体系统、重组微生物或真菌以及特定的核酸片段和多肽。
• Verfahren zur enzymatischen Herstellung eines 4-O-methylierten Zimtsäureamids
  申请人：Symrise AG

  公开号：EP3050971B1

  公开（公告）日：2020-06-24
• METHOD FOR BIOTECHNOLOGICAL PRODUCTION OF METHYLIZED CINNAMIC ACIDS AND CINNAMIC ACID ESTERS, METHYLIZED PHENETHYLAMINES AND THE COUPLING PRODUCTS THEREOF, PARTICULARLY OF CINNAMIC ACID AMIDES
  申请人：SYMRISE AG

  公开号：US20160281118A1

  公开（公告）日：2016-09-29

  The invention relates to providing both fermentative and biotechnological methods for producing 3,4-methylized cinnamic acids, 3,4-methylized cinnamic acid esters, 3,4-dimethoxyphenethylamine, and 4-methylized cinnamic acid amides using a 4′-O-methyltransferase, optionally in combination with further enzymes, wherein the enzymes are selected by means of metabolic engineering and operation have been adapted by targeted optimization, and compositions obtained by means of the method. The invention further relates to vector systems, recombinant microorganisms or fungi, and specific nucleic acid segments and polypeptides.
• Isolation and Synthesis of Melodamide A, a New Anti-inflammatory Phenolic Amide from the Leaves of Melodorum fruticosum
  作者：Hsiu-Hui Chan、Tsong-Long Hwang、Tran Thang、Yann-Lii Leu、Ping-Chung Kuo、Bui Nguyet、Do Dai、Tian-Shung Wu

  DOI：10.1055/s-0032-1328131

  日期：——

  Together with twelve known compounds (2-13), melodamide A (1), a new phenolic amide possessing p-quinol moiety, was purified and characterized from the methanolic extracts of the leaves of Melodorum fruticosum. The structure of melodamide A (1) was established with a combination of 2D NMR experiments, HR-ESI-MS and X-ray analyses. The other known compounds were identified by comparison of their spectroscopic and physical data with those reported in the literature. Moreover, some isolated compounds were examined for their inhibitory activity towards superoxide anion generation and elastase release in human neutrophils. Among the tested compounds, 1, 3, and 5 exhibited strong inhibition of superoxide anion generation with IC50 values ranging from 5.25 to 8.65 mu M. Furthermore, synthesis and biological evaluation of melodamide A (1) and its analogs (14a-p) were described.