3-[(3-bromo-4-methoxyphenyl)methyl]-5-(3,5-dibromo-4-hydroxyphenyl)-1H-pyrazin-2-one | 1422285-77-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-[(3-bromo-4-methoxyphenyl)methyl]-5-(3,5-dibromo-4-hydroxyphenyl)-1H-pyrazin-2-one
• CAS: 1422285-77-5
• 化学式: C₁₈H₁₃Br₃N₂O₃
• 分子量: 545.025
• InChiKey: WFNFQDPFYHHLBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  70.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[(3-bromo-4-methoxyphenyl)methyl]-5-(3,5-dibromo-4-hydroxyphenyl)-1H-pyrazin-2-one 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以42%的产率得到2,6-Dibromo-4-[6-[(3-bromo-4-methoxyphenyl)methyl]-5-chloropyrazin-2-yl]phenol
  参考文献：
  名称：

  The first total synthesis and biological evaluation of marine natural products ma’edamines A and B

  摘要：

  We have developed the first total syntheses of marine natural products ma'edamines A (18) and B (20). Structurally, they contain a pyrazine-2-(1H)-one core and were screened for antiproliferative activity on several cancer cell lines. Out of the six cell lines tested, ma'edamines A and B showed significant cytotoxicity against human colon cancer line COLO 205.(IC50 7.9 and 10.3 mu M, respectively), breast cancer cell line MCF-7 (IC50: 6.9 and 10.5 mu M, respectively) and human lung adenocarcinoma cell line A549 (IC50: 12.2 and 15.4 mu M, respectively). The apoptotic effect of ma'edamines was confirmed by comet assay. Hence ma'edamines are likely to be useful as leads for development of a new class of anti-cancer agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.033
• 作为产物：
  描述：

  2-bromo-1-(3,5-dibromo-4-hydroxyphenyl)ethanone 在 N-甲基吗啉 、 ammonium acetate 、 氢溴酸 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 作用下， 以 甲醇 、 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 68.0h， 生成 3-[(3-bromo-4-methoxyphenyl)methyl]-5-(3,5-dibromo-4-hydroxyphenyl)-1H-pyrazin-2-one
  参考文献：
  名称：

  The first total synthesis and biological evaluation of marine natural products ma’edamines A and B

  摘要：

  We have developed the first total syntheses of marine natural products ma'edamines A (18) and B (20). Structurally, they contain a pyrazine-2-(1H)-one core and were screened for antiproliferative activity on several cancer cell lines. Out of the six cell lines tested, ma'edamines A and B showed significant cytotoxicity against human colon cancer line COLO 205.(IC50 7.9 and 10.3 mu M, respectively), breast cancer cell line MCF-7 (IC50: 6.9 and 10.5 mu M, respectively) and human lung adenocarcinoma cell line A549 (IC50: 12.2 and 15.4 mu M, respectively). The apoptotic effect of ma'edamines was confirmed by comet assay. Hence ma'edamines are likely to be useful as leads for development of a new class of anti-cancer agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.033

文献信息

• The first total synthesis and biological evaluation of marine natural products ma’edamines A and B
  作者：Sanjay Saha、Ch. Venkata Ramana Reddy、T. Chiranjeevi、Uma Addepally、T.S. Chinta Rao、Balaram Patro

  DOI：10.1016/j.bmcl.2012.12.033

  日期：2013.2

  We have developed the first total syntheses of marine natural products ma'edamines A (18) and B (20). Structurally, they contain a pyrazine-2-(1H)-one core and were screened for antiproliferative activity on several cancer cell lines. Out of the six cell lines tested, ma'edamines A and B showed significant cytotoxicity against human colon cancer line COLO 205.(IC50 7.9 and 10.3 mu M, respectively), breast cancer cell line MCF-7 (IC50: 6.9 and 10.5 mu M, respectively) and human lung adenocarcinoma cell line A549 (IC50: 12.2 and 15.4 mu M, respectively). The apoptotic effect of ma'edamines was confirmed by comet assay. Hence ma'edamines are likely to be useful as leads for development of a new class of anti-cancer agents. (C) 2012 Elsevier Ltd. All rights reserved.