ethyl 3',4',5'-trimethoxythionocinnamate | 117666-86-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 3',4',5'-trimethoxythionocinnamate
• 英文别名: O-ethyl 3-(3,4,5-trimethoxyphenyl)prop-2-enethioate
• CAS: 117666-86-1
• 化学式: C₁₄H₁₈O₄S
• 分子量: 282.361
• InChiKey: JUABUGKQZWXRLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  69
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基肉桂酸乙酯 在 tetraphosphorus decasulfide 作用下， 以 1,4-二氧六环 为溶剂， 以63%的产率得到ethyl 3',4',5'-trimethoxythionocinnamate
  参考文献：
  名称：

  Novel natural product-based cinnamates and their thio and thiono analogs as potent inhibitors of cell adhesion molecules on human endothelial cells

  摘要：

  In the present study, we report the design and synthesis of novel analogs of cinnamates, thiocinnamates and thionocinnamates and evaluated the potencies of these analogs to inhibit TNF-alpha induced ICAM-1 expression on human endothelial cells. By using whole cell-ELISA, our screening data demonstrated that ethyl 3',4',5'-trimethoxythionocinnamate (ETMTC) is the most potent inhibitor of TNF-alpha induced ICAM-1, VCAM-1 and E-selectin. As functional consequences, ETMTC abrogated TNF-alpha induced adhesion of neutrophils to the endothelial monolayer. Structure activity relationship studies revealed the critical role of the chain-length of the alkyl group in the alcohol moiety, number of methoxy groups in the aromatic ring of the cinnamoyl moiety and the presence of the alpha, beta- C-C double bond in the thiocinnamates and thionocinnamates. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.008

文献信息

• Guerrera; Sarva; Siracusa, Farmaco, Edizione Scientifica, 1988, vol. 43, # 6, p. 551 - 558
  作者：Guerrera、Sarva、Siracusa、Ronsisvalle、Conforto、Dibennardo、Failla、Matera

  DOI：——

  日期：——
• Novel natural product-based cinnamates and their thio and thiono analogs as potent inhibitors of cell adhesion molecules on human endothelial cells
  作者：Sarvesh Kumar、Brajendra K. Singh、Pragya Arya、Shashwat Malhotra、Rajesh Thimmulappa、Ashok K. Prasad、Erik Van der Eycken、Carl E. Olsen、Anthony L. DePass、Shyam Biswal、Virinder S. Parmar、Balaram Ghosh

  DOI：10.1016/j.ejmech.2011.09.008

  日期：2011.11

  In the present study, we report the design and synthesis of novel analogs of cinnamates, thiocinnamates and thionocinnamates and evaluated the potencies of these analogs to inhibit TNF-alpha induced ICAM-1 expression on human endothelial cells. By using whole cell-ELISA, our screening data demonstrated that ethyl 3',4',5'-trimethoxythionocinnamate (ETMTC) is the most potent inhibitor of TNF-alpha induced ICAM-1, VCAM-1 and E-selectin. As functional consequences, ETMTC abrogated TNF-alpha induced adhesion of neutrophils to the endothelial monolayer. Structure activity relationship studies revealed the critical role of the chain-length of the alkyl group in the alcohol moiety, number of methoxy groups in the aromatic ring of the cinnamoyl moiety and the presence of the alpha, beta- C-C double bond in the thiocinnamates and thionocinnamates. (C) 2011 Elsevier Masson SAS. All rights reserved.