(E)-4-({(S)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-methyl-3-(1-methyl-1H-indol-3-yl)-butyrylamino]-3,3-dimethyl-butyryl}-methyl-amino)-2-methyl-but-2-enoic acid ethyl ester | 1027820-42-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (E)-4-({(S)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-methyl-3-(1-methyl-1H-indol-3-yl)-butyrylamino]-3,3-dimethyl-butyryl}-methyl-amino)-2-methyl-but-2-enoic acid ethyl ester
• 英文别名: ethyl (E)-4-[[(2S)-3,3-dimethyl-2-[[(2S)-3-methyl-3-(1-methylindol-3-yl)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]butanoyl]amino]butanoyl]-methylamino]-2-methylbut-2-enoate
• CAS: 1027820-42-3
• 化学式: C₃₄H₅₂N₄O₆
• 分子量: 612.81
• InChiKey: KORCWKKRZWJJFV-QGPNFHHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-4-({(S)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-methyl-3-(1-methyl-1H-indol-3-yl)-butyrylamino]-3,3-dimethyl-butyryl}-methyl-amino)-2-methyl-but-2-enoic acid ethyl ester 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 生成 (E)-4-({(S)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-methyl-3-(1-methyl-1H-indol-3-yl)-butyrylamino]-3,3-dimethyl-butyryl}-methyl-amino)-2-methyl-but-2-enoic acid
  参考文献：
  名称：

  Synthesis and Antimitotic/Cytotoxic Activity of Hemiasterlin Analogues

  摘要：

  The antimitotic sponge tripeptide hemiasterlin (1) and a number of structural analogues have been synthesized and evaluated in cell-based assays for both cytotoxic and antimitotic activity in order to explore the SAR for this promising anticancer drug lead. One synthetic analogue, SPA110 (8), showed more potent in vitro cytotoxicty and antimitotic activity than the natural product hemiasterlin (1), and consequently it has been subjected to thorough preclinical evaluation and targeted for clinical evaluation. The details of the synthesis of hemiasterlin (1) and the analogues and a discussion of how their biological activities vary with their structures are presented in this paper.

  DOI：

  10.1021/np020375t
• 作为产物：
  描述：

  methyl N-(tert-butoxycarbonyl)-N,β,β,1-tetramethyl-L-tryptophanate 在 lithium hydroxide 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 (E)-4-({(S)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-methyl-3-(1-methyl-1H-indol-3-yl)-butyrylamino]-3,3-dimethyl-butyryl}-methyl-amino)-2-methyl-but-2-enoic acid ethyl ester
  参考文献：
  名称：

  Synthesis and Antimitotic/Cytotoxic Activity of Hemiasterlin Analogues

  摘要：

  The antimitotic sponge tripeptide hemiasterlin (1) and a number of structural analogues have been synthesized and evaluated in cell-based assays for both cytotoxic and antimitotic activity in order to explore the SAR for this promising anticancer drug lead. One synthetic analogue, SPA110 (8), showed more potent in vitro cytotoxicty and antimitotic activity than the natural product hemiasterlin (1), and consequently it has been subjected to thorough preclinical evaluation and targeted for clinical evaluation. The details of the synthesis of hemiasterlin (1) and the analogues and a discussion of how their biological activities vary with their structures are presented in this paper.

  DOI：

  10.1021/np020375t