(2S)-2-amino-3-(3-bromo-4-methoxyphenyl)-N-[2-[3,5-dibromo-4-(3-bromopropoxy)phenyl]-2-oxoethyl]propanamide | 1422285-84-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-2-amino-3-(3-bromo-4-methoxyphenyl)-N-[2-[3,5-dibromo-4-(3-bromopropoxy)phenyl]-2-oxoethyl]propanamide
• CAS: 1422285-84-4
• 化学式: C₂₁H₂₂Br₄N₂O₄
• 分子量: 686.033
• InChiKey: ZXNZEEBMYWNMOC-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-2-amino-3-(3-bromo-4-methoxyphenyl)-N-[2-[3,5-dibromo-4-(3-bromopropoxy)phenyl]-2-oxoethyl]propanamide 、 3-(3-bromo-4-methoxybenzyl)-5-(3,5-dibromo-4-(3-bromopropoxy)phenyl)-5,6-dihydropyrazin-2(1H)-one 、 甲胺 以 四氢呋喃 为溶剂， 生成 ma'edamine
  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：

  1-[4-(3-bromopropoxy)-3,5-dibromophenyl]ethanone 在 盐酸 、 氢溴酸 、 溴 、 三乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 1,4-二氧六环 、 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 76.0h， 生成 (2S)-2-amino-3-(3-bromo-4-methoxyphenyl)-N-[2-[3,5-dibromo-4-(3-bromopropoxy)phenyl]-2-oxoethyl]propanamide 、 3-(3-bromo-4-methoxybenzyl)-5-(3,5-dibromo-4-(3-bromopropoxy)phenyl)-5,6-dihydropyrazin-2(1H)-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.