(2E,2'E)-N,N'-(3,3'-(butane-1,4-diylbis(methylazanediyl))bis(propane-3,1-diyl))bis(2-(benzyloxyimino)-3-(3,5-dibromo-4-methoxyphenyl)propanamide) | 1262993-77-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2E,2'E)-N,N'-(3,3'-(butane-1,4-diylbis(methylazanediyl))bis(propane-3,1-diyl))bis(2-(benzyloxyimino)-3-(3,5-dibromo-4-methoxyphenyl)propanamide)
• 英文别名: dibenzylspermatinamine；(2E)-3-(3,5-dibromo-4-methoxyphenyl)-N-[3-[4-[3-[[(2E)-3-(3,5-dibromo-4-methoxyphenyl)-2-phenylmethoxyiminopropanoyl]amino]propyl-methylamino]butyl-methylamino]propyl]-2-phenylmethoxyiminopropanamide
• CAS: 1262993-77-0
• 化学式: C₄₆H₅₆Br₄N₆O₆
• 分子量: 1108.6
• InChiKey: BSTHEDXAFSVYIU-NSXGZDRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  62
• 可旋转键数：
  27
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2E,2'E)-N,N'-(3,3'-(butane-1,4-diylbis(methylazanediyl))bis(propane-3,1-diyl))bis(2-(benzyloxyimino)-3-(3,5-dibromo-4-methoxyphenyl)propanamide) 在 氢气 、 钯 作用下， 以 1,4-二氧六环 、 溶剂黄146 为溶剂， 反应 20.0h， 以72%的产率得到spermatinamine
  参考文献：
  名称：

  An improved total synthesis of spermatinamine, an inhibitor of isoprenylcysteine carboxy methyltransferase

  摘要：

  An improved total synthesis of spermatinamine, an inhibitor of the anticancer target, isoprenylcysteine carboxy methyltransferase (Icmt) was accomplished from the commercially available 3,4-dibromo-4-hydroxybenzaldehyde via a high yielding reaction sequence in an overall yield of 31%. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.164
• 作为产物：
  描述：

  3,5-二溴-4-甲氧基苯甲醛 在 sodium ethanolate 、 sodium acetate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 生成 (2E,2'E)-N,N'-(3,3'-(butane-1,4-diylbis(methylazanediyl))bis(propane-3,1-diyl))bis(2-(benzyloxyimino)-3-(3,5-dibromo-4-methoxyphenyl)propanamide)
  参考文献：
  名称：

  Versatile Routes to Marine Sponge Metabolites through Benzylidene Rhodanines

  摘要：

  The first total synthesis of the marine natural products Psammaplin C and Tokaradine A is described. Benzylidene rhodanines were utilized as versatile intermediates toward the synthesis of seven brominated marine sponge metabolites through the optimization of protection group strategies. Spermatinamine demonstrated good inhibition of all cancer cell lines tested, in particular the leukemia K562 and colon cancer HT29 cell lines.

  DOI：

  10.1021/ol303057a

文献信息

• An improved total synthesis of spermatinamine, an inhibitor of isoprenylcysteine carboxy methyltransferase
  作者：Nisar Ullah、Shamsuddeen A. Haladu、Basem A. Mosa

  DOI：10.1016/j.tetlet.2010.10.164

  日期：2011.1

  An improved total synthesis of spermatinamine, an inhibitor of the anticancer target, isoprenylcysteine carboxy methyltransferase (Icmt) was accomplished from the commercially available 3,4-dibromo-4-hydroxybenzaldehyde via a high yielding reaction sequence in an overall yield of 31%. (C) 2010 Elsevier Ltd. All rights reserved.
• Versatile Routes to Marine Sponge Metabolites through Benzylidene Rhodanines
  作者：Suresh K. Kottakota、Mathew Benton、Dimitrios Evangelopoulos、Juan D. Guzman、Sanjib Bhakta、Timothy D. McHugh、Mark Gray、Paul W. Groundwater、Emma C. L. Marrs、John D. Perry、J. Jonathan Harburn

  DOI：10.1021/ol303057a

  日期：2012.12.21

  The first total synthesis of the marine natural products Psammaplin C and Tokaradine A is described. Benzylidene rhodanines were utilized as versatile intermediates toward the synthesis of seven brominated marine sponge metabolites through the optimization of protection group strategies. Spermatinamine demonstrated good inhibition of all cancer cell lines tested, in particular the leukemia K562 and colon cancer HT29 cell lines.