N-[2-(S)-hydroxy-2-(4-hydroxy-phenyl)ethyl]-3-(4-hydroxy-3-methoxy-phenyl)acrylamide

• 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: N-[2-(S)-hydroxy-2-(4-hydroxy-phenyl)ethyl]-3-(4-hydroxy-3-methoxy-phenyl)acrylamide
• 英文别名: (2S,E)-N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl] ferulamide；(2S,E)-N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]ferulamide；(S)–N-trans-feruloyloctopamine；(7'S)-N-trans-feruloyloctopamine；S-(-)-N-trans-feruloyloctopamine；(S)-N-trans-feruloyl-octopamine；(E)-N-[(2S)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
• 化学式: C₁₈H₁₉NO₅
• 分子量: 329.353
• InChiKey: VJSCHQMOTSXAKB-UOWSJYKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  99
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[2-(S)-hydroxy-2-(4-hydroxy-phenyl)ethyl]-3-(4-hydroxy-3-methoxy-phenyl)acrylamide 以 甲醇 为溶剂， 反应 96.0h， 生成 (7'S)-N-cis-feruloyloctopamine
  参考文献：
  名称：

  马齿苋阿魏酰酰胺的紫外光转化及其对 IL-6 诱导的 STAT3 激活的抑制作用研究

  摘要：

  从马齿苋中分离出两种新的阿魏酰胺，N-顺式木槿酰胺 (5) 和 (7'S)-N-顺式阿魏酰去甲变肾上腺素 (9)，以及八种已知的阿魏酰酰胺，以及十种分离出的阿魏酰的几何转化通过紫外光验证酰胺。阿魏酰酰胺的结构是基于光谱数据和与文献数据的比较确定的。核磁共振数据表明，在正常实验室光照条件下，分离出的化合物的结构显示出顺式/反式异构化。因此，通过波长为 254 nm 的紫外光评估阿魏酰酰胺的顺式和反式异构体的转化率和稳定性。在紫外线照射 96 小时后，23.2%–35.0% 的顺式和反式异构体转化为反式异构体。长期稳定性测试没有显示任何显着变化。在收集的所有化合物和转化混合物中，化合物 6 对 Hep3B 细胞中 IL-6 诱导的 STAT3 激活的抑制作用最强，IC50 值为 0.2 μM。本研究首次验证了阿魏酰酰胺的转化率和平衡比。这些结果表明，这种天然材料可能为治疗涉及 IL-6 和 STAT3

  DOI：

  10.3390/molecules21070865
• 作为产物：
  描述：

  (S)-(+)-acetic acid 4-(2-benzyloxycarbonylamino-1-hydroxy-ethyl)phenyl ester 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~25.0 ℃ 、101.33 kPa 条件下， 反应 19.0h， 生成 N-[2-(S)-hydroxy-2-(4-hydroxy-phenyl)ethyl]-3-(4-hydroxy-3-methoxy-phenyl)acrylamide
  参考文献：
  名称：

  Identification from a Combinatorial Library of a Small Molecule that Selectively Induces Apoptosis in Cancer Cells

  摘要：

  The selective induction of death in cancer cells is a major challenge in modern medicine. In this communication we describe the synthesis of an 88-membered combinatorial library, and the subsequent evaluation of these compounds for their ability to selectively induce apoptosis in cancerous cells. A compound was identified from the library that induces apoptosis in U-937 and HL-60 cell lines. This compound is a remarkably selective pro-apoptotic agent for these cancer cell lines, as it does not induce significant death in noncancerous white blood cells, even at concentrations as high as 1000 muM.

  DOI：

  10.1021/ja038043d

文献信息

• Highly Enantioselective Henry Reactions in Water Catalyzed by a Copper Tertiary Amine Complex and Applied in the Synthesis of (S)-N-trans-Feruloyl Octopamine
  作者：Guoyin Lai、Fengfeng Guo、Yueqin Zheng、Yang Fang、Haigang Song、Kun Xu、Sujing Wang、Zhenggen Zha、Zhiyong Wang

  DOI：10.1002/chem.201002915

  日期：2011.1.24

  It's in the water! A new copper tertiary amine complex was prepared and applied in asymmetric Henry reactions in water and in the short synthesis of (S)‐N‐trans‐feruloyl octopamine. This catalytic system provided an approach to the enantioselective Henry reaction of aldehydes with hydroxyl substituents (see graphic).

  在水里！制备了一种新的铜叔胺络合物，并将其用于水中的不对称亨利反应中，以及在短时间内合成（S）-N-反式-阿魏酸八胺的过程中。该催化体系为醛与羟基取代基的对映选择性亨利反应提供了一种方法（见图）。
• Compounds and methods for treatment of cancer and modulation of programmed cell death for melanoma and other cancer cells
  申请人：Hergenrother J. Paul

  公开号：US20050197511A1

  公开（公告）日：2005-09-08

  Compounds and related methods for synthesis, and the use of compounds and combination therapies for the treatment of cancer and modulation of apoptosis in cells are disclosed. The generation of synthetic combinatorial libraries and the evaluation of library member compounds regarding induction of apoptosis selectively in cancer cells are disclosed. Compounds, methods of making the compounds, and therapeutic methods with application against breast cancer cells, melanoma cancer cells, colon cancer cells, and other cancer cells are described.

  本文披露了合成化合物及相关方法，并使用化合物和联合疗法治疗癌症和调节细胞凋亡。本文还披露了合成组合库的生成以及评估库成员化合物在选择性诱导癌细胞凋亡方面的应用。描述了化合物、制备化合物的方法以及应用于乳腺癌细胞、黑色素瘤癌细胞、结肠癌细胞和其他癌症细胞的治疗方法。
• [EN] COMPOUNDS AND METHODS FOR TREATMENT OF CANCER AND MODULATION OF PROGRAMMED CELL DEATH FOR MELANOMA AND OTHER CANCER CELLS<br/>[FR] COMPOSES ET PROCEDES DE TRAITEMENT DU CANCER ET MODULATION DE LA MORT CELLULAIRE PROGRAMMEE DE MELANOMES ET D'AUTRES CELLULES CANCEREUSES
  申请人：UNIV ALABAMA

  公开号：WO2005044191A3

  公开（公告）日：2005-10-20
• US7632972B2
  申请人：——

  公开号：US7632972B2

  公开（公告）日：2009-12-15
• Identification from a Combinatorial Library of a Small Molecule that Selectively Induces Apoptosis in Cancer Cells
  作者：Vitaliy Nesterenko、Karson S. Putt、Paul J. Hergenrother

  DOI：10.1021/ja038043d

  日期：2003.12.1

  The selective induction of death in cancer cells is a major challenge in modern medicine. In this communication we describe the synthesis of an 88-membered combinatorial library, and the subsequent evaluation of these compounds for their ability to selectively induce apoptosis in cancerous cells. A compound was identified from the library that induces apoptosis in U-937 and HL-60 cell lines. This compound is a remarkably selective pro-apoptotic agent for these cancer cell lines, as it does not induce significant death in noncancerous white blood cells, even at concentrations as high as 1000 muM.