{4-[6-(1-hydroxy-1-methylethyl)-5,6-dihydrobenzo[1,2-b;5,4-b']difuran-2-yl]phenoxy}acetic acid ethyl ester | 1310328-32-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: {4-[6-(1-hydroxy-1-methylethyl)-5,6-dihydrobenzo[1,2-b;5,4-b']difuran-2-yl]phenoxy}acetic acid ethyl ester
• 英文别名: Ethyl 2-[4-[6-(2-hydroxypropan-2-yl)-5,6-dihydrofuro[3,2-f][1]benzofuran-2-yl]phenoxy]acetate
• CAS: 1310328-32-5
• 化学式: C₂₃H₂₄O₆
• 分子量: 396.44
• InChiKey: UOZFNORMCSDERU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  78.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  bis-(2,4-tert-butoxycarbonyloxy)-benzaldehyde 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium tetrahydroborate 、 copper(l) iodide 、 pyridine hydrofluoride 、 一氯化碘 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 间氯过氧苯甲酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 {4-[6-(1-hydroxy-1-methylethyl)-5,6-dihydrobenzo[1,2-b;5,4-b']difuran-2-yl]phenoxy}acetic acid ethyl ester
  参考文献：
  名称：

  HIF-1α inhibitors: Synthesis and biological evaluation of novel moracin O and P analogues

  摘要：

  The natural products moracins O and P exhibited potent in vitro inhibitory activity against hypoxia-inducible factor (HIF-1), which is a key mediator during adaptation of cancer cells to tumour hypoxia. Systematic variations of the structures of benzofuran type moracins were made and structure-activity relationship analysis showed the importance of the 2-arylbenzofuran ring and the (R)-configuration of the core scaffold. Further evaluation of the representative compound 5 showed its inhibitory effect on HIF-1 alpha protein accumulation and target gene expression under hypoxia. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.022

文献信息

• HIF-1α inhibitors: Synthesis and biological evaluation of novel moracin O and P analogues
  作者：Yan Xia、Yinglan Jin、Navneet Kaur、Yongseok Choi、Kyeong Lee

  DOI：10.1016/j.ejmech.2011.03.022

  日期：2011.6

  The natural products moracins O and P exhibited potent in vitro inhibitory activity against hypoxia-inducible factor (HIF-1), which is a key mediator during adaptation of cancer cells to tumour hypoxia. Systematic variations of the structures of benzofuran type moracins were made and structure-activity relationship analysis showed the importance of the 2-arylbenzofuran ring and the (R)-configuration of the core scaffold. Further evaluation of the representative compound 5 showed its inhibitory effect on HIF-1 alpha protein accumulation and target gene expression under hypoxia. (C) 2011 Elsevier Masson SAS. All rights reserved.