(S)-14-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-10-oxo-2,5,8-trioxa-11-azapentadecan-15-oic acid | 1444302-35-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-14-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-10-oxo-2,5,8-trioxa-11-azapentadecan-15-oic acid
• CAS: 1444302-35-5
• 化学式: C₂₆H₃₂N₂O₈
• 分子量: 500.549
• InChiKey: FATHJBAXSAMZJD-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  36.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  132.42
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  、 (S)-14-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-10-oxo-2,5,8-trioxa-11-azapentadecan-15-oic acid 在 N-羟基-7-氮杂苯并三氮唑 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.25h， 生成
  参考文献：
  名称：

  Orthogonal Chemistry for the Synthesis of Thiocoraline–Triostin Hybrids. Exploring their Structure–Activity Relationship

  摘要：

  The natural compounds triostin and thiocoraline are potent antitumor agents that act as DNA bisintercalators. From a pharmaceutical point of view, these compounds are highly attractive although they present a low pharmacokinetic profile, in part due to their low solubility. Synthetically, they represent a tour de force because no robust strategies have been developed to access a broad range of these bicyclic (depsi)peptides in a straightforward manner. Here we describe solid-phase strategies to synthesize new bisintercalators, such as thiocoraline triostin hybrids, as well is analogues bearing soluble tags. Orthogonal protection schemes (up to, five from: Fmoc, Boc Alloc, pNZ, o-NBS, and Troc), together with the right concourse of the coupling reagents (HOSu, HOBt, HOAt, Oxyma, EDC, DIPCDI, PyAOP, PyBOP, HATU, COMU), were crucial to establish the synthetic plan. In vitro studies and structure activity relationships have been shown trends in the structure activity relationship that Will facilitate the design of new bisintercalators.

  DOI：

  10.1021/jm4006093
• 作为产物：
  描述：

  2-(2-(2-甲氧基乙氧基)乙氧基)乙酸 、 Nα-Fmoc-L-2,3-二氨基丙酸 在 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以0.9 g的产率得到(S)-14-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-10-oxo-2,5,8-trioxa-11-azapentadecan-15-oic acid
  参考文献：
  名称：

  Orthogonal Chemistry for the Synthesis of Thiocoraline–Triostin Hybrids. Exploring their Structure–Activity Relationship

  摘要：

  The natural compounds triostin and thiocoraline are potent antitumor agents that act as DNA bisintercalators. From a pharmaceutical point of view, these compounds are highly attractive although they present a low pharmacokinetic profile, in part due to their low solubility. Synthetically, they represent a tour de force because no robust strategies have been developed to access a broad range of these bicyclic (depsi)peptides in a straightforward manner. Here we describe solid-phase strategies to synthesize new bisintercalators, such as thiocoraline triostin hybrids, as well is analogues bearing soluble tags. Orthogonal protection schemes (up to, five from: Fmoc, Boc Alloc, pNZ, o-NBS, and Troc), together with the right concourse of the coupling reagents (HOSu, HOBt, HOAt, Oxyma, EDC, DIPCDI, PyAOP, PyBOP, HATU, COMU), were crucial to establish the synthetic plan. In vitro studies and structure activity relationships have been shown trends in the structure activity relationship that Will facilitate the design of new bisintercalators.

  DOI：

  10.1021/jm4006093

文献信息

• Synthesis of PNA Oligoether Conjugates
  作者：Alice Ghidini、Peter Steunenberg、Merita Murtola、Roger Strömberg

  DOI：10.3390/molecules19033135

  日期：——

  diaminopropionic acid residues. Single and double conjugation of 2-(2-(2-aminoethoxy)ethoxy)ethanol was obtained using carbonyldimidazole. Using a post PNA-assembly coupling procedure the building block 2-(2-(2-(benzoyloxy)ethoxy)ethoxy)acetic acid multiple attachment of 2-(2-(2-hydroxyethoxy)ethoxy)acetyl groups to both N-terminal and β-amino groups of inserted diaminopropionic acids residues was achieved

  已经探索了几种不同的方法用于将低聚醚与具有内部或 N 末端放置的二氨基丙酸残基的 PNA 缀合。使用羰基二咪唑获得2-(2-(2-氨基乙氧基)乙氧基)乙醇的单缀合和双缀合。使用 PNA 组装后偶联程序，将 2-(2-(2-(2-羟基乙氧基)乙氧基)乙酰基基团 2-(2-(2-(苯甲酰氧基)乙氧基)乙氧基)乙酸多重连接到两个 N 末端并获得了插入的二氨基丙酸残基的β-氨基。使用新的低聚醚官能化氨基酸允许在在线机器辅助合成过程中包含低聚醚缀合物，这还允许组合用于连接不同低聚醚和新铜灵共缀合以及氨基糖缀合的方法。