Propanoic acid, 3-mercapto-2-[(tetrahydro-4-methoxy-2H-pyran-4-yl)oxy]-, methyl ester, (S)- | 133904-68-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Propanoic acid, 3-mercapto-2-[(tetrahydro-4-methoxy-2H-pyran-4-yl)oxy]-, methyl ester, (S)-
• 英文别名: methyl (2S)-2-(4-methoxyoxan-4-yl)oxy-3-sulfanylpropanoate
• CAS: 133904-68-4
• 化学式: C₁₀H₁₈O₅S
• 分子量: 250.316
• InChiKey: MNUJSTWXWWZTOM-MRVPVSSYSA-N

物化性质

• 沸点：
  360.0±42.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.63
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  53.99
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Propanoic acid, 3-mercapto-2-[(tetrahydro-4-methoxy-2H-pyran-4-yl)oxy]-, methyl ester, (S)- 在 氢氧化钾 、 苄基三乙基氯化铵 、 sodium hydride 、 sodium iodide 作用下， 反应 1.5h， 生成 (S)-methyl 2-<<4-(4-methoxytetrahydropyranoyl)>oxy>3-<<<<<<<2-(trimethylsilyl)ethyl>oxy>carbonyl><2-(3-indolyl)ethyl>amino>oxy>methyl>thio>propanoate
  参考文献：
  名称：

  Antiviral and antitumor structure-activity relationship studies on tetracyclic eudistomines

  摘要：

  The in vitro antiviral and antitumor activities of (-)-debromoeudistomin K (1a) and 10 structural analogues (1b-1j and 11) were evaluated. The synthesis was accomplished with an intramolecular Pictet-Spengler condensation reaction as the key step. This examination revealed some structural and stereochemical features that are important for both the antiviral and antitumor activities. The most striking points for activity are the necessity to have the correct natural stereochemistry at both C(1) and C(13b) and the presence of the C(1)-NH2 substituent. As was revealed before with naturally isolated eudistomins a substituent in the indole ring greatly influences the biological activity. The 5-OMe derivative Ih shows high potency in both antiviral and antitumor models.

  DOI：

  10.1021/jm00095a019
• 作为产物：
  描述：

  (R)-2-(4-Methoxy-tetrahydro-pyran-4-yloxy)-3-(toluene-4-sulfonyloxy)-propionic acid methyl ester 在 sodium methylate 、 caesium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 生成 Propanoic acid, 3-mercapto-2-[(tetrahydro-4-methoxy-2H-pyran-4-yl)oxy]-, methyl ester, (S)-
  参考文献：
  名称：

  Antiviral and antitumor structure-activity relationship studies on tetracyclic eudistomines

  摘要：

  The in vitro antiviral and antitumor activities of (-)-debromoeudistomin K (1a) and 10 structural analogues (1b-1j and 11) were evaluated. The synthesis was accomplished with an intramolecular Pictet-Spengler condensation reaction as the key step. This examination revealed some structural and stereochemical features that are important for both the antiviral and antitumor activities. The most striking points for activity are the necessity to have the correct natural stereochemistry at both C(1) and C(13b) and the presence of the C(1)-NH2 substituent. As was revealed before with naturally isolated eudistomins a substituent in the indole ring greatly influences the biological activity. The 5-OMe derivative Ih shows high potency in both antiviral and antitumor models.

  DOI：

  10.1021/jm00095a019

文献信息

• Synthesis and Evaluation of Acyl Protein Thioesterase 1 (APT1) Inhibitors
  作者：Markus Biel、Patrick Deck、Athanassios Giannis、Herbert Waldmann

  DOI：10.1002/chem.200501128

  日期：2006.5.15

  Recently, an enzyme, acyl protein thioesterase 1 (APT1), that may play a regulatory role in the palmitoylation cycle of H-Ras and G-protein alpha subunits, was purified. Motivated by this work, several inhibitors of APT1 were designed, synthesized and biologically evaluated leading to highly active compounds.

  脂质修饰的蛋白质在重要的生物学过程中起着决定性作用，例如信号转导，细胞骨架的组织和囊泡转运。这些蛋白质的脂化对于正确的生物学功能是必不可少的。在脂质修饰中，烯丙基化和肉豆蔻酰基化是众所周知的。但是，棕榈酰化的机制仍在研究中。最近，纯化了一种可能在H-Ras和G蛋白α亚基的棕榈酰化循环中起调节作用的酰基蛋白硫酯酶1（APT1）酶。受这项工作的启发，设计，合成了多种APT1抑制剂，并对其进行了生物学评估，从而产生了高活性的化合物。