(2S,4R)-4-(2-((1S,3S)-1-acetoxy-4-methyl-3-((2S,3S)-3-methyl-2-((R)-1-methylpiperidine-2-carboxamido)pentanamido)pentyl)thiazole-4-carboxamido)-2-methyl-5-phenylpentanoic acid | 1467092-05-2

• 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: (2S,4R)-4-(2-((1S,3S)-1-acetoxy-4-methyl-3-((2S,3S)-3-methyl-2-((R)-1-methylpiperidine-2-carboxamido)pentanamido)pentyl)thiazole-4-carboxamido)-2-methyl-5-phenylpentanoic acid
• 英文别名: (2S,4R)-4-[[2-[(1S,3S)-1-acetyloxy-4-methyl-3-[[(2S,3S)-3-methyl-2-[[(2R)-1-methylpiperidine-2-carbonyl]amino]pentanoyl]amino]pentyl]-1,3-thiazole-4-carbonyl]amino]-2-methyl-5-phenylpentanoic acid
• CAS: 1467092-05-2
• 化学式: C₃₇H₅₅N₅O₇S
• 分子量: 713.939
• InChiKey: RXKZEOMBVZELEA-MIEMEYRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  50
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  195
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  (2S,4R)-methyl 4-(2-((1S,3S)-1-hydroxy-4-methyl-3-((2S,3S)-3-methyl-2-((R)-1-methylpiperidine-2-carboxamido)pentanamido)pentyl)thiazole-4-carboxamido)-2-methyl-5-phenylpentanoate 在 吡啶 、 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 生成 (2S,4R)-4-(2-((1S,3S)-1-acetoxy-4-methyl-3-((2S,3S)-3-methyl-2-((R)-1-methylpiperidine-2-carboxamido)pentanamido)pentyl)thiazole-4-carboxamido)-2-methyl-5-phenylpentanoic acid
  参考文献：
  名称：

  Synthesis and cytotoxicity evaluation of diastereoisomers and N-terminal analogues of tubulysin-U

  摘要：

  Tubulysins are potent anti-mitotic natural compounds and a scalable and efficient synthetic route for generation of its analogues has been developed and extended to the synthesis of diastereoisomers and N-terminal analogues of tubulysin-U. Structure-activity-relationship studies on these synthetic analogues reaffirmed the significance of native stereochemistry of tubulysins for optimal biological activity and cytotoxicity. However, while modification of Tup stereochemistry has only minor effect on the tubulysins cytotoxicity, Tuv stereochemistry is critically important and modification of either Tuv stereo-centre produced a dramatic drop in cytotoxicity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.010

文献信息

• Synthesis and cytotoxicity evaluation of diastereoisomers and N-terminal analogues of tubulysin-U
  作者：P. Sreejith Shankar、Serena Bigotti、Paolo Lazzari、Ilaria Manca、Marco Spiga、Monica Sani、Matteo Zanda

  DOI：10.1016/j.tetlet.2013.09.010

  日期：2013.11

  Tubulysins are potent anti-mitotic natural compounds and a scalable and efficient synthetic route for generation of its analogues has been developed and extended to the synthesis of diastereoisomers and N-terminal analogues of tubulysin-U. Structure-activity-relationship studies on these synthetic analogues reaffirmed the significance of native stereochemistry of tubulysins for optimal biological activity and cytotoxicity. However, while modification of Tup stereochemistry has only minor effect on the tubulysins cytotoxicity, Tuv stereochemistry is critically important and modification of either Tuv stereo-centre produced a dramatic drop in cytotoxicity. (C) 2013 Elsevier Ltd. All rights reserved.