ethyl (S)-N-tert-butoxycarbonylvalyl-(2E,4S)-N-methyl-4-amino-2,5-dimethylhex-2-enoate | 500229-49-2

• 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: ethyl (S)-N-tert-butoxycarbonylvalyl-(2E,4S)-N-methyl-4-amino-2,5-dimethylhex-2-enoate
• 英文别名: ethyl (E,4S)-2,5-dimethyl-4-[methyl-[(2S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]hex-2-enoate
• CAS: 500229-49-2
• 化学式: C₂₁H₃₈N₂O₅
• 分子量: 398.543
• InChiKey: IYODEPFQVJWRBR-ODQHEUEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 ethyl (S)-N-tert-butoxycarbonylvalyl-(2E,4S)-N-methyl-4-amino-2,5-dimethylhex-2-enoate 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 ethyl (S)-valyl-(2E,4S)-N-methyl-4-amino-2,5-dimethylhex-2-enoate trifluoroacetate
  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：

  、 (3S,4E)-6-ethoxy-N,2,5-trimethyl-6-oxohex-4-en-3-aminium 2,2,2-trifluoroacetate 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以121 mg的产率得到ethyl (S)-N-tert-butoxycarbonylvalyl-(2E,4S)-N-methyl-4-amino-2,5-dimethylhex-2-enoate
  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

文献信息

• Hemiasterlin derivatives and uses thereof in the treatment of cancer
  申请人：Kowalczyk J. James

  公开号：US20080051434A1

  公开（公告）日：2008-02-28

  The present invention provides compounds having formula (I): and additionally provides methods for the synthesis thereof and methods for the use thereof in the treatment of cancer, wherein R 1 -R 7 , X 1 , X 2 , R, Q, and n are as defined herein.
• Hemiasterlin Derivatives and Uses Thereof
  申请人：Campagna Silvio A.

  公开号：US20080108820A1

  公开（公告）日：2008-05-08

  The present invention provides compounds having formula (I): and additionally provides methods for the synthesis thereof and methods for the use thereof in the treatment of cancer, wherein R 1 -R 7 , X 1 , X 2 , R, Q, and n are as defined herein.
• HEMIASTERLIN DERIVATIVES AND USES THEREOF IN THE TREATMENT OF CANCER
  申请人：KOWALCZYK James J.

  公开号：US20100063095A1

  公开（公告）日：2010-03-11

  The present invention provides compounds having formula (I): and additionally provides methods for the synthesis thereof and methods for the use thereof in the treatment of cancer, wherein R 1 -R 7 , X 1 , X 2 , R, Q, and n are as defined herein.
• US7528152B2
  申请人：——

  公开号：US7528152B2

  公开（公告）日：2009-05-05
• US7585976B2
  申请人：——

  公开号：US7585976B2

  公开（公告）日：2009-09-08