5-bromoverongamine | 218931-98-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-bromoverongamine
• 英文别名: (E)-N-(2-(1H-imidazol-5-yl)ethyl)-3-(3,5-dibromo-4-methoxyphenyl)-2-(hydroxyimino)propanamide；bromoverongamine；(2E)-3-(3,5-dibromo-4-methoxyphenyl)-2-hydroxyimino-N-[2-(1H-imidazol-5-yl)ethyl]propanamide
• CAS: 218931-98-7
• 化学式: C₁₅H₁₆Br₂N₄O₃
• 分子量: 460.125
• InChiKey: HCLLNEPYJROFBM-FYJGNVAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  99.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (E)-N-(2-(1H-imidazol-4-yl)ethyl)-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 6.0h， 以89%的产率得到5-bromoverongamine
  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

• Total syntheses of the bromotyrosine-derived natural products ianthelline, 5-bromoverongamine and JBIR-44
  作者：James W. Shearman、Rebecca M. Myers、Thomas M. Beale、James D. Brenton、Steven V. Ley

  DOI：10.1016/j.tetlet.2010.07.016

  日期：2010.9

  The total syntheses of the bromotyrosine-derived natural products ianthelline, 5-bromoverongamine and JBIR-44 are described and their cytotoxic activity in a cervical cancer (HeLa) cell line and human umbilical vein endothelial cells (HUVECs) are reported. (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.