[(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 | 1017294-04-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: [(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
• CAS: 1017294-04-0
• 化学式: C₅₈H₅₆N₄O₁₄
• 分子量: 1033.1
• InChiKey: RNTCUNIEXLYSJR-GBPHBDQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  76
• 可旋转键数：
  24
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  224
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (Z)-2-(3',5`-diamino-4`-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)ethene 、 O-乙酰基-N-[(9H-芴-9-甲氧基)羰基]-L-丝氨酸 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 反应 4.0h， 以19%的产率得到[(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
  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