| 166759-17-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• CAS: 166759-17-7
• 化学式: C₆₆H₁₁₂O₁₄S₂Si
• 分子量: 1221.82
• InChiKey: IJQIEXOYHFLNQQ-WDNIRUJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.03
• 重原子数：
  83.0
• 可旋转键数：
  29.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  152.74
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  N-甲基甲酰胺 、 在 3 A molecular sieve 、 4-甲基苯磺酸吡啶 、 对苯二酚 作用下， 以 苯 为溶剂， 反应 6.5h， 以42%的产率得到
  参考文献：
  名称：

  Aplyronine A, a Potent Antitumor Substance of Marine Origin, Aplyronines B and C, and Artificial Analogues:  Total Synthesis and Structure−Cytotoxicity Relationships

  摘要：

  The enantioselective total synthesis of aplyronine A (1), a potent antitumor substance of marine origin, was achieved by a convergent-approach Three segments 4, 5, and 6, corresponding to the C5-C11, C21-C27, and C28-C34 portions of aplyronine A (1), were prepared using:the Evans aldol reaction and the Sharpless epoxidation as key steps. The coupling reaction of 4 with iodide 7 followed by julia olefination with sulfone 8 gave the C5-C20 segment 9, while the julia coupling reaction between segments 5 and 6 provided the C21-C34 segment 10. Julia olefination between segments 9 and 10 and the subsequent four-carbon homologation reaction led to seco acid 83, which was converted into aplyronine A (1) by Yamaguchi lactonization followed by the introduction of two amino acids. The use of the [(3,4-dimethoxybenzyl)oxy]methyl group as a protecting group for the hydroxyl at C29 was crucial for this synthesis. The enantioselective synthesis of two natural congeners, aplyronines B (2) acid C (3), was also carried out using the intermediates for the synthesis of 1, which determined the absolute stereostructures of 2 and 3 unambiguously. To study the structure-cytotoxicity relationships of aplyronines, artificial analogues of 1 were synthesized and their cytotoxicities were evaluated: the trimethylserine moiety, two hydroxyl groups, and the side-chain portion in 1 turned out to be important in the potent cytotoxicity shown by 1. Biological studies with aplyronine A (1) showed that 1 inhibited polymerization of G-actin to F-actin and depolymerized F-actin to G-actin.

  DOI：

  10.1021/jo9606113
• 作为产物：
  描述：

  [(3R,4R,5S,6R,9S,10S,11R)-11-[(2S,4E,6R,8R,10E,12S,15R,16R,17R,18R,20E,22E)-16-[tert-butyl(dimethyl)silyl]oxy-6,12-dimethoxy-8,11,15,17-tetramethyl-18-(methylsulfanylmethoxy)-24-oxo-1-oxacyclotetracosa-4,10,20,22-tetraen-2-yl]-6-[(3,4-dimethoxyphenyl)methoxymethoxy]-1-hydroxy-3,5,9-trimethyl-10-(methylsulfanylmethoxy)dodecan-4-yl] acetate 在 戴斯-马丁氧化剂 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 以73%的产率得到
  参考文献：
  名称：

  aplyronines B和C的绝对立体化学和合成，aplyronine A的同源物，aplyronine A是一种有效的海洋来源抗肿瘤物质

  摘要：

  对映体选择性地实现了对aplyronines B和C，aplyronine A的同类物的合成，建立了它们的立体结构。

  DOI：

  10.1016/0040-4039(95)00921-x