carbonic acid tert-butyl ester 3-hydroxy-2,2-dimethylchroman-7-yl ester | 1310328-60-9

• 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: carbonic acid tert-butyl ester 3-hydroxy-2,2-dimethylchroman-7-yl ester
• 英文别名: Tert-butyl (3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-7-yl) carbonate
• CAS: 1310328-60-9
• 化学式: C₁₆H₂₂O₅
• 分子量: 294.348
• InChiKey: XHEQBLLHMUFZSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  carbonic acid tert-butyl ester 3-hydroxy-2,2-dimethylchroman-7-yl ester 在 盐酸 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-benzyloxy-benzoic acid 3-hydroxy-2,2-dimethyl-chroman-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 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以49%的产率得到carbonic acid tert-butyl ester 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.