(E)-(S)-4-({2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-methyl-3-phenyl-butyrylamino]-3-fluoro-3-methyl-butyryl}-methyl-amino)-2,5-dimethyl-hex-2-enoic acid | 757242-20-9

• 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)-(S)-4-({2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-methyl-3-phenyl-butyrylamino]-3-fluoro-3-methyl-butyryl}-methyl-amino)-2,5-dimethyl-hex-2-enoic acid
• CAS: 757242-20-9
• 化学式: C₃₁H₄₈FN₃O₆
• 分子量: 577.737
• InChiKey: SONONZCOTZJDCL-LMGUHIFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  41.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  116.25
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E)-(S)-4-({2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-methyl-3-phenyl-butyrylamino]-3-fluoro-3-methyl-butyryl}-methyl-amino)-2,5-dimethyl-hex-2-enoic acid 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (E,4S)-4-[[(2R)-3-fluoro-3-methyl-2-[[(2S)-3-methyl-2-(methylamino)-3-phenylbutanoyl]amino]butanoyl]-methylamino]-2,5-dimethylhex-2-enoic acid 、 (E,4S)-4-[[(2S)-3-fluoro-3-methyl-2-[[(2S)-3-methyl-2-(methylamino)-3-phenylbutanoyl]amino]butanoyl]-methylamino]-2,5-dimethylhex-2-enoic acid
  参考文献：
  名称：

  Tubulin inhibitors. Synthesis and biological activity of HTI-286 analogs with B-segment heterosubstituents

  摘要：

  Modifications of the B-segment of HTI-286 (2) produced a class of analogs incorporating heteroatom-substituents. The structure-activity relationship was studied. Analogs bearing methylsulfide and fluoride groups exhibited potency comparable to that of the parent compound HTI-286 and to paclitaxel in cytotoxicity assays against KB-3-1 cell lines. These analogs were more potent than paclitaxel against P-glycoprotein expressing KB-8-5 and KB-V1 cell lines. Several analogs showed strong inhibition of tubulin polymerization. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.077
• 作为产物：
  描述：

  2-((tert-butoxycarbonyl)amino)-3-fluoro-3-methylbutanoic acid 在 盐酸 、 lithium hydroxide 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 生成 (E)-(S)-4-({2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-methyl-3-phenyl-butyrylamino]-3-fluoro-3-methyl-butyryl}-methyl-amino)-2,5-dimethyl-hex-2-enoic acid
  参考文献：
  名称：

  Tubulin inhibitors. Synthesis and biological activity of HTI-286 analogs with B-segment heterosubstituents

  摘要：

  Modifications of the B-segment of HTI-286 (2) produced a class of analogs incorporating heteroatom-substituents. The structure-activity relationship was studied. Analogs bearing methylsulfide and fluoride groups exhibited potency comparable to that of the parent compound HTI-286 and to paclitaxel in cytotoxicity assays against KB-3-1 cell lines. These analogs were more potent than paclitaxel against P-glycoprotein expressing KB-8-5 and KB-V1 cell lines. Several analogs showed strong inhibition of tubulin polymerization. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.077