4-bromobenzoic acid 3-hydroxy-2,2-dimethylchroman-7-yl ester | 1310328-55-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-bromobenzoic acid 3-hydroxy-2,2-dimethylchroman-7-yl ester
• 英文别名: (3-Hydroxy-2,2-dimethyl-3,4-dihydrochromen-7-yl) 4-bromobenzoate
• CAS: 1310328-55-2
• 化学式: C₁₈H₁₇BrO₄
• 分子量: 377.235
• InChiKey: CMEPYQARTSTIIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-bromobenzoic acid 3-hydroxy-2,2-dimethylchroman-7-yl ester 、 3-硝基苯硼酸 在 四(三苯基膦)钯 、 碳酸氢钠 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 5.0h， 以22.5%的产率得到3'-nitrobiphenyl-4-carboxylic acid 3-hydroxy-2,2-dimethylchroman-7-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 盐酸 、 对甲苯磺酸 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 生成 4-bromobenzoic acid 3-hydroxy-2,2-dimethylchroman-7-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.