(E)-4-(3,5-dihydroxystyryl)phenyl isobutyrate | 1217011-26-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-4-(3,5-dihydroxystyryl)phenyl isobutyrate
• 英文别名: 4'-isobutyrate trans-resveratrol；4'-isobutyrate resveratrol；(E)-4-(3,5-dihydroxystyryl)phenol isobutyrate；[4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]phenyl] 2-methylpropanoate
• CAS: 1217011-26-1
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: IDMBWYRYQMEURZ-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-4-(3,5-bis(methoxymethoxy)styryl)phenol isobutyrate 在 盐酸 作用下， 以 乙醚 为溶剂， 以82%的产率得到(E)-4-(3,5-dihydroxystyryl)phenyl isobutyrate
  参考文献：
  名称：

  白藜芦醇4'-酯类似物的合成及其在恶性黑色素瘤和胰腺细胞株中的评价

  摘要：

  合成了疾病预防剂白藜芦醇的4'-酯类似物，并评估了其作为抗黑素瘤和胰腺癌药物的潜力。使用脱羰Heck偶联剂组装受保护的二苯乙烯核结构。与正常的NHDF细胞相比，DM443和DM738细胞具有4'-乙酸和棕榈酸酯类似物的选择性活性。

  DOI：

  10.1016/j.bmcl.2009.12.006

文献信息

• Selective esterification of the polyphenol resveratrol at the 4′-position
  作者：Mark J. Acerson、Merritt B. Andrus

  DOI：10.1016/j.tetlet.2013.12.019

  日期：2014.1

  Selective esterification of the polyphenol resveratrol was performed under thermodynamic conditions using NaH and acid anhydrides to directly access 4 '-esters. Standard conditions with acetyl chloride and pyridine showed poor selectivity, favoring esterification at the 3-position. The extended 4 '-phenolate anion is generated in preference to the 3-phenolate under the new anhydride-sodium hydride-DMSO conditions. Acylation occurs to access the 4 '-ester products with modest selectivity and yield with minimal formation of the 3-monoester, 3,5-diester, and triester products. (C) 2013 Elsevier Ltd. All rights reserved.
• Anti-Inflammatory Compounds and Uses Thereof
  申请人：MEDICON PHARMACEUTICALS, INC.

  公开号：US20190307780A1

  公开（公告）日：2019-10-10

  Compounds of the general formula are disclosed with activity towards treating diseases related to inflammation, such as cancer, neurodegenerative and cardiovascular diseases. Pharmaceutical compositions and methods of use are also described.
• ANTI-INFLAMMATORY COMPOUNDS AND USES THEREOF
  申请人：Medicon Pharmaceuticals, Inc.

  公开号：US20220409638A1

  公开（公告）日：2022-12-29

  Compounds of the general formula are disclosed with activity towards treating diseases related to inflammation, such as cancer, neurodegenerative and cardiovascular diseases. Pharmaceutical compositions and methods of use are also described.
• US7585997B2
  申请人：——

  公开号：US7585997B2

  公开（公告）日：2009-09-08
• Synthesis of 4′-ester analogs of resveratrol and their evaluation in malignant melanoma and pancreatic cell lines
  作者：Yong Wong、Gregory Osmond、Kenneth I. Brewer、Douglas S. Tyler、Merritt B. Andrus

  DOI：10.1016/j.bmcl.2009.12.006

  日期：2010.2

  4′-Ester analogs of the disease preventative agent resveratrol were synthesized and evaluated for their potential as anti-melanoma and pancreatic cancer agents. A decarbonylative Heck coupling was used to assemble the protected stilbene core structure. The 4′-acetate and the palmitoate analogs demonstrated selective activity with DM443 and DM738 cells over normal NHDF cells.

  合成了疾病预防剂白藜芦醇的4'-酯类似物，并评估了其作为抗黑素瘤和胰腺癌药物的潜力。使用脱羰Heck偶联剂组装受保护的二苯乙烯核结构。与正常的NHDF细胞相比，DM443和DM738细胞具有4'-乙酸和棕榈酸酯类似物的选择性活性。