(2S)-2-amino-N-[3-[[(2S)-2-amino-3-hydroxypropanoyl]amino]-2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl]-3-hydroxypropanamide | 1017294-06-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2S)-2-amino-N-[3-[[(2S)-2-amino-3-hydroxypropanoyl]amino]-2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl]-3-hydroxypropanamide
• CAS: 1017294-06-2
• 化学式: C₂₄H₃₂N₄O₈
• 分子量: 504.54
• InChiKey: WZGSOUQWRGYODQ-XFCCUVRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  188
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  [(2S)-3-[3-[[(2S)-3-acetyloxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoyl]amino]-2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]anilino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-oxopropyl] acetate 在 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.5h， 以16%的产率得到(2S)-2-amino-N-[3-[[(2S)-2-amino-3-hydroxypropanoyl]amino]-2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl]-3-hydroxypropanamide
  参考文献：
  名称：

  Combretastatin Dinitrogen-Substituted Stilbene Analogues as Tubulin-Binding and Vascular-Disrupting Agents

  摘要：

  Several stilbenoid compounds having structural similarity to the combretastatin group of natural products and characterized by the incorporation of two nitrogen-bearing groups (amine, nitro, serinamide) have been prepared by chemical synthesis and evaluated in terms of biochemical and biological activity. The 2',3'-diamino B-ring analogue 17 demonstrated remarkable cytotoxicity against selected human cancer cell lines in vitro (average GI(50) = 13.9 nM) and also showed good activity in regard to inhibition of tubulin assembly (IC50 = 2.8 mu M). In addition, a single dose (10 mg/kg) of compound 17 caused a 40% tumor-selective blood flow shutdown in tumor-bearing SCID mice at 24 h, thus suggesting the potential value of this compound and its corresponding salt formulations as new vascular-disrupting agents.

  DOI：

  10.1021/np070377j

文献信息

• Combretastatin Dinitrogen-Substituted Stilbene Analogues as Tubulin-Binding and Vascular-Disrupting Agents
  作者：Rogelio Siles、J. Freeland Ackley、Mallinath B. Hadimani、John J. Hall、Benon E. Mugabe、Rajsekhar Guddneppanavar、Keith A. Monk、Jean-Charles Chapuis、George R. Pettit、David J. Chaplin、Klaus Edvardsen、Mary Lynn Trawick、Charles M. Garner、Kevin G. Pinney

  DOI：10.1021/np070377j

  日期：2008.3.1

  Several stilbenoid compounds having structural similarity to the combretastatin group of natural products and characterized by the incorporation of two nitrogen-bearing groups (amine, nitro, serinamide) have been prepared by chemical synthesis and evaluated in terms of biochemical and biological activity. The 2',3'-diamino B-ring analogue 17 demonstrated remarkable cytotoxicity against selected human cancer cell lines in vitro (average GI(50) = 13.9 nM) and also showed good activity in regard to inhibition of tubulin assembly (IC50 = 2.8 mu M). In addition, a single dose (10 mg/kg) of compound 17 caused a 40% tumor-selective blood flow shutdown in tumor-bearing SCID mice at 24 h, thus suggesting the potential value of this compound and its corresponding salt formulations as new vascular-disrupting agents.