N-(3,5-dibromo-4-hydroxyphenethyl)-N-methylacetamide | 1207456-10-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(3,5-dibromo-4-hydroxyphenethyl)-N-methylacetamide
• 英文别名: N-[2-(3,5-dibromo-4-hydroxyphenyl)ethyl]-N-methylacetamide
• CAS: 1207456-10-7
• 化学式: C₁₁H₁₃Br₂NO₂
• 分子量: 351.038
• InChiKey: HRSQZZKPILWVHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3,5-dibromo-4-hydroxyphenethyl)-N-methylacetamide 、 N-Boc-3-氨基丙基溴 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 tert-butyl 3-(2,6-dibromo-4-(2-(N-methylacetamido)ethyl)phenoxy)propylcarbamate
  参考文献：
  名称：

  Isolation, Synthesis, and Biological Activity of Aphrocallistin, an Adenine-Substituted Bromotyramine Metabolite from the Hexactinellida Sponge Aphrocallistes beatrix

  摘要：

  A new adenine-substituted bromotyrosine-derived metabolite designated as aphrocallistin (1) has been isolated from the deep-water Hexactinellida sponge Aphrocallistes beatrix. Its structure was elucidated on the basis of spectral data and confirmed through a convergent, modular total synthetic route that is amenable toward future analogue preparation. Aphrocallistin inhibits the growth of a panel of human tumor cell lines with IC50 values ranging from 7.5 to > 100 mu M and has been shown to induce G1 cell cycle arrest in the PANC-1 pancreatic carcinoma cell line. Aphrocallistin has been fully characterized in the NCI cancer cell line panel and has undergone in vitro ADME pharmacological profiling.

  DOI：

  10.1021/np900183v
• 作为产物：
  描述：

  N-methyl-N-(4-hydroxyphenethyl)acetamide 在 溴 、 溶剂黄146 作用下， 反应 3.0h， 生成 N-(3,5-dibromo-4-hydroxyphenethyl)-N-methylacetamide
  参考文献：
  名称：

  Isolation, Synthesis, and Biological Activity of Aphrocallistin, an Adenine-Substituted Bromotyramine Metabolite from the Hexactinellida Sponge Aphrocallistes beatrix

  摘要：

  A new adenine-substituted bromotyrosine-derived metabolite designated as aphrocallistin (1) has been isolated from the deep-water Hexactinellida sponge Aphrocallistes beatrix. Its structure was elucidated on the basis of spectral data and confirmed through a convergent, modular total synthetic route that is amenable toward future analogue preparation. Aphrocallistin inhibits the growth of a panel of human tumor cell lines with IC50 values ranging from 7.5 to > 100 mu M and has been shown to induce G1 cell cycle arrest in the PANC-1 pancreatic carcinoma cell line. Aphrocallistin has been fully characterized in the NCI cancer cell line panel and has undergone in vitro ADME pharmacological profiling.

  DOI：

  10.1021/np900183v

文献信息

• Isolation, Synthesis, and Biological Activity of Aphrocallistin, an Adenine-Substituted Bromotyramine Metabolite from the Hexactinellida Sponge <i>Aphrocallistes beatrix</i>
  作者：Amy E. Wright、Gregory P. Roth、Jennifer K. Hoffman、Daniela B. Divlianska、Diana Pechter、Susan H. Sennett、Esther A. Guzmán、Patricia Linley、Peter J. McCarthy、Tara P. Pitts、Shirley A. Pomponi、John K. Reed

  DOI：10.1021/np900183v

  日期：2009.6.26

  A new adenine-substituted bromotyrosine-derived metabolite designated as aphrocallistin (1) has been isolated from the deep-water Hexactinellida sponge Aphrocallistes beatrix. Its structure was elucidated on the basis of spectral data and confirmed through a convergent, modular total synthetic route that is amenable toward future analogue preparation. Aphrocallistin inhibits the growth of a panel of human tumor cell lines with IC50 values ranging from 7.5 to > 100 mu M and has been shown to induce G1 cell cycle arrest in the PANC-1 pancreatic carcinoma cell line. Aphrocallistin has been fully characterized in the NCI cancer cell line panel and has undergone in vitro ADME pharmacological profiling.