3,4-dihydro-5,7-dimethoxy-2H-1-benzopyran-3-ol | 445388-24-9

• 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: 3,4-dihydro-5,7-dimethoxy-2H-1-benzopyran-3-ol
• 英文别名: 5,7-dimethoxy-3,4-dihydro-2H-chromen-3-ol
• CAS: 445388-24-9
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: RCNNFNOFZFSEBK-UHFFFAOYSA-N

物化性质

• 沸点：
  373.1±42.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-5,7-dimethoxy-2H-1-benzopyran-3-ol 在 吡啶 、 偶氮二甲酸二异丙酯 、 二苯基膦叠氮化物 、 水 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 61.0h， 生成 N-(5,7-dimethoxychroman-3-yl)-3-methoxybenzamide
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationships of EGCG Analogues, a Recently Identified Hsp90 Inhibitor

  摘要：

  Epigallocatechin-3-gallate (EGCG), the principal polyphenol isolated from green tea, was recently shown to inhibit Hsp90; however, structure activity relationships for this natural product have not yet been produced. Herein, we report the synthesis and biological evaluation of EGCG analogues to establish structure activity relationships between EGCG and Hsp90. All four rings as well as the linker connecting the C- and the D-rings were systematically investigated, which led to the discovery of compounds that inhibit Hs90 and display improvement in efficacy over EGCG. Antiproliferative activity of all the analogues was determined against MCF-7 and SKBr3 cell lines and Hsp90 inhibitory activity of the four most potent analogues was further evaluated by Western blot analyses and degradation of Hsp90-dependent client proteins. The prenyl-substituted aryl ester of 3,5-dihydroxychroman-3-ol ring system was identified as a novel scaffold that exhibits Hsp90 inhibitory activity.

  DOI：

  10.1021/jo401027r
• 作为产物：
  描述：

  5,7-dimethoxychromone 在 sodium hydroxide 、 硼烷 作用下， 生成 3,4-dihydro-5,7-dimethoxy-2H-1-benzopyran-3-ol
  参考文献：
  名称：

  Differential Inhibition of polymerase and Strand-Transfer Activities of HIV-1 Reverse Transcriptase

  摘要：

  A new class of inhibitors of HIV-1 reverse transcriptase obtained by the systematic structural simplification of epicatechin and epigallocatechin gallates are also shown here to inhibit DNA-strand-transfer, a process critical to the completion of the HIV-1-RT reproduction and to recombination-associated mutation of the virus. Up to 80-fold selectivity for DNA-strand-transfer inhibition over polymerase inhibition was observed for a defined subset of these agents. Such specific DNA-strand-transfer inhibitors may have important therapeutic potential. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00827-7

文献信息

• An Au-Catalyzed Cyclialkylation of Electron-Rich Arenes with Epoxides To Prepare 3-Chromanols
  作者：Zhangjie Shi、Chuan He

  DOI：10.1021/ja031953a

  日期：2004.5.1

  A gold-catalyzed cyclialkylation of electron-rich arenes with tethered epoxides afforded 3-chromanols stereospecifically.

  金催化的富电子芳烃与环氧化物的环烷基化反应得到立体特异性的 3-苯并二氢呋喃。
• Synthesis and Structure–Activity Relationships of EGCG Analogues, a Recently Identified Hsp90 Inhibitor
  作者：Anuj Khandelwal、Jessica A. Hall、Brian S. J. Blagg

  DOI：10.1021/jo401027r

  日期：2013.8.16

  Epigallocatechin-3-gallate (EGCG), the principal polyphenol isolated from green tea, was recently shown to inhibit Hsp90; however, structure activity relationships for this natural product have not yet been produced. Herein, we report the synthesis and biological evaluation of EGCG analogues to establish structure activity relationships between EGCG and Hsp90. All four rings as well as the linker connecting the C- and the D-rings were systematically investigated, which led to the discovery of compounds that inhibit Hs90 and display improvement in efficacy over EGCG. Antiproliferative activity of all the analogues was determined against MCF-7 and SKBr3 cell lines and Hsp90 inhibitory activity of the four most potent analogues was further evaluated by Western blot analyses and degradation of Hsp90-dependent client proteins. The prenyl-substituted aryl ester of 3,5-dihydroxychroman-3-ol ring system was identified as a novel scaffold that exhibits Hsp90 inhibitory activity.
• Differential Inhibition of polymerase and Strand-Transfer Activities of HIV-1 Reverse Transcriptase
  作者：L.M.Viranga Tillekeratne、Angela Sherette、Jennifer A Fulmer、Lynn Hupe、Donald Hupe、Sam Gabbara、James A Peliska、Richard A Hudson

  DOI：10.1016/s0960-894x(01)00827-7

  日期：2002.2

  A new class of inhibitors of HIV-1 reverse transcriptase obtained by the systematic structural simplification of epicatechin and epigallocatechin gallates are also shown here to inhibit DNA-strand-transfer, a process critical to the completion of the HIV-1-RT reproduction and to recombination-associated mutation of the virus. Up to 80-fold selectivity for DNA-strand-transfer inhibition over polymerase inhibition was observed for a defined subset of these agents. Such specific DNA-strand-transfer inhibitors may have important therapeutic potential. (C) 2002 Elsevier Science Ltd. All rights reserved.