(Z)-5-hydroxy-2-(4-bromobenzylidene)benzofuran-3(2H)-one | 1261274-05-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: (Z)-5-hydroxy-2-(4-bromobenzylidene)benzofuran-3(2H)-one
• 英文别名: (Z)-2-(4-bromobenzylidene)-5-hydroxybenzo[b]furan-3-one；(2Z)-2-[(4-bromophenyl)methylidene]-5-hydroxy-1-benzofuran-3-one
• CAS: 1261274-05-8
• 化学式: C₁₅H₉BrO₃
• 分子量: 317.139
• InChiKey: AGNXABPJBSLWNH-AUWJEWJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-5-hydroxy-2-(4-bromobenzylidene)benzofuran-3(2H)-one 、 棕榈酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以83.3%的产率得到(Z)-2-(4-bromobenzylidene)-3-oxo-2,3-dihydrobenzofuran-5-yl palmitate
  参考文献：
  名称：

  Synthesis and biological evaluation of new flavonoid fatty acid esters with anti-adipogenic and enhancing glucose consumption activities

  摘要：

  Oleoyl Formononetin (OF) has good weight loss activity and hypolipidemic activity, could improve insulin sensitivity and suppress adipogenesis. To acquire better biological activities, three series of flavonoid fatty acid esters were designed and synthesized by optimizing the structure of OF. Their bioactivities were assayed in vitro. Some of these novel compounds could effectively inhibit preadipocyte proliferation and adipogenesis. Moreover, they could enhance glucose consumption in adipocytes notably. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.063
• 作为产物：
  描述：

  2'-hydroxy-5'-methoxymethoxyacetophenone 在 吡啶 、 盐酸 、 mercury(II) diacetate 、 水 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 1.5h， 生成 (Z)-5-hydroxy-2-(4-bromobenzylidene)benzofuran-3(2H)-one
  参考文献：
  名称：

  Synthesis and biological evaluation of new flavonoid fatty acid esters with anti-adipogenic and enhancing glucose consumption activities

  摘要：

  Oleoyl Formononetin (OF) has good weight loss activity and hypolipidemic activity, could improve insulin sensitivity and suppress adipogenesis. To acquire better biological activities, three series of flavonoid fatty acid esters were designed and synthesized by optimizing the structure of OF. Their bioactivities were assayed in vitro. Some of these novel compounds could effectively inhibit preadipocyte proliferation and adipogenesis. Moreover, they could enhance glucose consumption in adipocytes notably. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.063

文献信息

• Design, synthesis and discovery of 5-hydroxyaurone derivatives as growth inhibitors against HUVEC and some cancer cell lines
  作者：Huimin Cheng、Lianwen Zhang、Yingxue Liu、Shaopeng Chen、Hao Cheng、Xin Lu、Zhuxia Zheng、Guo-Chun Zhou

  DOI：10.1016/j.ejmech.2010.09.061

  日期：2010.12

  A series of 4'-substituted 5-hydroxyaurone derivatives were synthesized and their inhibitory activities against the proliferation of endothelial cells and two cancer cell lines were studied. Some of these compounds functioned as potent inhibitors against the proliferation of endothelial cells and cancer cells but possessed much weaker cytotoxic activities against non-cancer cell line of CCC-HPF-1. It was demonstrated that two most active compounds 16 and 27 effectively inhibited in vitro endothelial cell motility and tube formation, which are basic properties of endothelial cells for angiogenesis. Moreover, 16 and 27 also showed significant activities against in vitro cancer cell invasion, indicating that they have potential to inhibit cancer metastasis. These composite results suggest that 4'-substituted 5-hydroxyaurone is indeed a candidate structural scaffold for anticancer agent targeting activated endothelial cells and fast-proliferating cancer cells. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Synthesis and biological evaluation of new flavonoid fatty acid esters with anti-adipogenic and enhancing glucose consumption activities
  作者：Wei Zhao、Jie Sun、Hua Xiang、Yan-yan Zeng、Xiao-bo Li、Hong Xiao、De-ying Chen、Ren-ling Ma

  DOI：10.1016/j.bmc.2011.03.063

  日期：2011.5

  Oleoyl Formononetin (OF) has good weight loss activity and hypolipidemic activity, could improve insulin sensitivity and suppress adipogenesis. To acquire better biological activities, three series of flavonoid fatty acid esters were designed and synthesized by optimizing the structure of OF. Their bioactivities were assayed in vitro. Some of these novel compounds could effectively inhibit preadipocyte proliferation and adipogenesis. Moreover, they could enhance glucose consumption in adipocytes notably. (C) 2011 Elsevier Ltd. All rights reserved.