2,5-dibromo-3,4-dihydroxybenzyl alcohol | 750637-62-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,5-dibromo-3,4-dihydroxybenzyl alcohol
• 英文别名: 3,6-Dibromo-4-(hydroxymethyl)benzene-1,2-diol
• CAS: 750637-62-8
• 化学式: C₇H₆Br₂O₃
• 分子量: 297.931
• InChiKey: NLXXHGMMQNEDKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-dibromo-3,4-dihydroxybenzyl alcohol 、 丙醇 以 水 为溶剂， 反应 6.0h， 以86%的产率得到2,5-dibromo-3,4-dihydroxybenzyl n-propyl ether
  参考文献：
  名称：

  In-vitro Cytotoxic Activities of the Major Bromophenols of the Red Alga Polysiphonia lanosa and Some Novel Synthetic Isomers

  摘要：

  Bioassay-guided fractionation was applied to the cytotoxic chloroform fraction of the red alga Polysiphonia lanosa, The major compounds of the most active fraction were identified using GLC-MS analysis as lanosol (1), methyl, ethyl, and n-propyl ethers of lanosol (1a, 1b, and 1c, respectively), and aldehyde of lanosol (2), although 1b appears to be an artifact arising during the fractionation procedure. These compounds and other known bromophenols were synthesized in addition to four novel isomers (3, 3a-c). The cytotoxic activities of all the synthetic compounds were determined against DLD-1 cells using the MTT assay. Compounds with IC50 < 20 mumol were also tested against HCT-116 cells. Compound 3c (2,5-dibromo-3,4-dihydroxybenzyl n-propyl ether) was the most active compound against both cell lines (IC50 = 1.72 and 0.80 mumol, respectively), and its effect on the cell cycle was studied using flow cytometry.

  DOI：

  10.1021/np0305268
• 作为产物：
  描述：

  2,5-dibromoprotocatechualdehyde 在 钾硼氢 作用下， 以 phosphate buffer 为溶剂， 反应 0.17h， 以64%的产率得到2,5-dibromo-3,4-dihydroxybenzyl alcohol
  参考文献：
  名称：

  In-vitro Cytotoxic Activities of the Major Bromophenols of the Red Alga Polysiphonia lanosa and Some Novel Synthetic Isomers

  摘要：

  Bioassay-guided fractionation was applied to the cytotoxic chloroform fraction of the red alga Polysiphonia lanosa, The major compounds of the most active fraction were identified using GLC-MS analysis as lanosol (1), methyl, ethyl, and n-propyl ethers of lanosol (1a, 1b, and 1c, respectively), and aldehyde of lanosol (2), although 1b appears to be an artifact arising during the fractionation procedure. These compounds and other known bromophenols were synthesized in addition to four novel isomers (3, 3a-c). The cytotoxic activities of all the synthetic compounds were determined against DLD-1 cells using the MTT assay. Compounds with IC50 < 20 mumol were also tested against HCT-116 cells. Compound 3c (2,5-dibromo-3,4-dihydroxybenzyl n-propyl ether) was the most active compound against both cell lines (IC50 = 1.72 and 0.80 mumol, respectively), and its effect on the cell cycle was studied using flow cytometry.

  DOI：

  10.1021/np0305268

文献信息

• In<i>-</i>vitro Cytotoxic Activities of the Major Bromophenols of the Red Alga<i> Polysiphonia </i><i>l</i><i>anosa</i> and Some Novel Synthetic Isomers
  作者：Nagwa A. Shoeib、Michael C. Bibby、Gerald Blunden、Peter A. Linley、David J. Swaine、Richard T. Wheelhouse、Colin W. Wright

  DOI：10.1021/np0305268

  日期：2004.9.1

  Bioassay-guided fractionation was applied to the cytotoxic chloroform fraction of the red alga Polysiphonia lanosa, The major compounds of the most active fraction were identified using GLC-MS analysis as lanosol (1), methyl, ethyl, and n-propyl ethers of lanosol (1a, 1b, and 1c, respectively), and aldehyde of lanosol (2), although 1b appears to be an artifact arising during the fractionation procedure. These compounds and other known bromophenols were synthesized in addition to four novel isomers (3, 3a-c). The cytotoxic activities of all the synthetic compounds were determined against DLD-1 cells using the MTT assay. Compounds with IC50 < 20 mumol were also tested against HCT-116 cells. Compound 3c (2,5-dibromo-3,4-dihydroxybenzyl n-propyl ether) was the most active compound against both cell lines (IC50 = 1.72 and 0.80 mumol, respectively), and its effect on the cell cycle was studied using flow cytometry.

表征谱图