(2S,10S,10aR)-10-benzoyloxy-5-oxo-9-pent-4-enoyloxymethyl-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-2-yl (4'S,5'R)-4'-(2-allyloxyphenyl)-3'-benzoyl-2'-(4-methoxyphenyl)oxazolidine-5-carboxylate | 1255794-66-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,10S,10aR)-10-benzoyloxy-5-oxo-9-pent-4-enoyloxymethyl-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-2-yl (4'S,5'R)-4'-(2-allyloxyphenyl)-3'-benzoyl-2'-(4-methoxyphenyl)oxazolidine-5-carboxylate
• CAS: 1255794-66-1
• 化学式: C₅₂H₄₈N₂O₁₁
• 分子量: 876.96
• InChiKey: QUFFERNPPOOKRQ-QNZFTWOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.29
• 重原子数：
  65.0
• 可旋转键数：
  16.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  147.21
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2S,10S,10aR)-10-benzoyloxy-5-oxo-9-pent-4-enoyloxymethyl-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-2-yl (4'S,5'R)-4'-(2-allyloxyphenyl)-3'-benzoyl-2'-(4-methoxyphenyl)oxazolidine-5-carboxylate 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以82%的产率得到(2S,10S,10aR)-10-benzoyloxy-5-oxo-9-(pent-4-enoyloxymethyl)-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-2-yl (2'R,3'S)-3'-(2-allyloxyphenyl)-3'-benzoylamino-2'-hydroxypropanoate
  参考文献：
  名称：

  Design and synthesis of de novo cytotoxic alkaloids by mimicking the bioactive conformation of paclitaxel

  摘要：

  Novel paclitaxel-mimicking alkaloids were designed and synthesized based on a bioactive conformation of paclitaxel, that is, REDOR-Taxol. The alkaloid 2 bearing a 5-7-6 tricyclic scaffold mimics REDOR-Taxol best among the compounds designed and was found to be the most potent compound against several drug-sensitive and drug-resistant human cancer cell lines. MD simulation study on the paclitaxel mimics 1 and 2 as well as REDOR-Taxol bound to the 1JFF tubulin structure was quite informative to evaluate the level of mimicking. The MD simulation study clearly distinguishes the 5-6-6 and 5-7-6 tricyclic scaffolds, and also shows substantial difference in the conformational stability of the tubulin-bound structures between 2 and REDOR-Taxol. The latter may account for the large difference in potency, and provides critical information for possible improvement in the future design of paclitaxel mimics. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.069
• 作为产物：
  描述：

  HO-Leu-Asp-Lys-Trp-Ala-Ser-Leu-Trp-Asn-Trp-Phe-NH2 在 咪唑 、 羟胺 作用下， 以 N-甲基吡咯烷酮 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 (2S,10S,10aR)-10-benzoyloxy-5-oxo-9-pent-4-enoyloxymethyl-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-2-yl (4'S,5'R)-4'-(2-allyloxyphenyl)-3'-benzoyl-2'-(4-methoxyphenyl)oxazolidine-5-carboxylate
  参考文献：
  名称：

  对映体纯N-羟基氨基酸的亚硝基保护基团：用于化学选择性连接的N末端肽羟基胺的合成†

  摘要：

  对映纯的合成 ñ -亚苄基N-羟基-α-氨基酸的硝酮及其使用标准品的掺入Fmoc描述了基于肽的化学成固体支持的肽链。脱保护和树脂裂解得到ñ-末端肽羟胺，它们是与 C-末端肽α-酮酸。该通用途径适用于多种不同的N-末端残基，并为肽羟胺的固相合成提供了通用方法。

  DOI：

  10.1039/c004490c