methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(1R,3S,14R)-18-ethyl-3-methoxycarbonyl-14-[[(2S)-2-methoxycarbonylpyrrolidin-1-yl]methyl]-5,16-diazatetracyclo[14.3.1.04,12.06,11]icosa-4(12),6,8,10,18-pentaen-3-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate | 1613232-10-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 鸡蛋花型生物碱
• 英文名称: methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(1R,3S,14R)-18-ethyl-3-methoxycarbonyl-14-[[(2S)-2-methoxycarbonylpyrrolidin-1-yl]methyl]-5,16-diazatetracyclo[14.3.1.04,12.06,11]icosa-4(12),6,8,10,18-pentaen-3-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate
• CAS: 1613232-10-2；1654010-03-3
• 化学式: C₅₄H₆₉N₅O₁₀
• 分子量: 948.169
• InChiKey: UJSDIMPPELQZCW-TZZICCFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  69
• 可旋转键数：
  14
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  163
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  、 L-脯氨酸甲酯 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以16%的产率得到methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(1R,3S,14R)-18-ethyl-3-methoxycarbonyl-14-[[(2S)-2-methoxycarbonylpyrrolidin-1-yl]methyl]-5,16-diazatetracyclo[14.3.1.04,12.06,11]icosa-4(12),6,8,10,18-pentaen-3-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate
  参考文献：
  名称：

  One-Pot Synthesis of Vinca Alkaloids–Phomopsin Hybrids

  摘要：

  Hybrids of vinca alkaloids and phomopsin A have been elaborated with the aim of interfering with the "vinca site" and the "peptide site" of the vinca domain in tubulin. They were synthesized by an efficient one-pot procedure that directly links the octahydrophomopsin lateral chain to the velbenamine moiety of 7'-homo-anhydrovinblastine. In their modeled complexes with tubulin, these hybrids were found to superimpose nicely on the tubulin-bound structures of vinblastine and phomopsin A. This good matching can account for the fact that two of them are very potent inhibitors of microtubules assembly and are cytotoxic against four cancer cell lines.

  DOI：

  10.1021/jm500530v