3,5-bis(benzyloxy)benzoic acid 2-(1-hydroxy-1-methylethyl)-2,3-dihydrobenzofuran-6-yl ester | 1310328-43-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-bis(benzyloxy)benzoic acid 2-(1-hydroxy-1-methylethyl)-2,3-dihydrobenzofuran-6-yl ester
• 英文别名: [2-(2-Hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-6-yl] 3,5-bis(phenylmethoxy)benzoate
• CAS: 1310328-43-8
• 化学式: C₃₂H₃₀O₆
• 分子量: 510.587
• InChiKey: XOLMGQFYSARTSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,5-bis(benzyloxy)benzoic acid 2-(1-hydroxy-1-methylethyl)-2,3-dihydrobenzofuran-6-yl ester 在 5% Pd(II)/C(eggshell) 、 氢气 作用下， 以 甲醇 为溶剂， 以51.3%的产率得到3,5-dihydroxybenzoic acid 2-(1-hydroxy-1-methylethyl)-2,3-dihydrobenzofuran-6-yl 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
• 作为产物：
  描述：

  Tert-butyl [3-hydroxy-4-(3-methylbut-2-enyl)phenyl] carbonate 在 4-二甲氨基吡啶 、 间氯过氧苯甲酸 、 N,N'-二环己基碳二亚胺 、 lithium hydroxide 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 3,5-bis(benzyloxy)benzoic acid 2-(1-hydroxy-1-methylethyl)-2,3-dihydrobenzofuran-6-yl 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.